Objective

To synthesize 66 Ugi adducts using Ugi 4CR following Explan005 .The target compound were ranked 55 -124 (except 58) in the DEXP014-V2B file from D-EXP014 . The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this summary post .

Procedure

To sixty nine vials, labeled 181# (55-124 except 58) and charged with methanol, four reactants [aldehyde, amine, acid and isocyanide] (0.5mmol each) were added to each in that order. After each addition, the resulting solution was vortexed for 30seconds (or more) . The vials were capped tight and left at room temperature. The vials which formed solid precipitates or crystals were decanted and the solid was washed with methanol (3x 500uL) and dried under vacuum to obtain corresponding Ugi products.

Exp-Lib Rank
Aldehyde
Amine
Acid
Isocyanide
Ppt (Y/N) & Yield
181-55
Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
5-Methylfurfurylamine
(0.5mmol-55.7uL)
2,6-dihydroxybenzoic aicd
(0.5mmol-77.0mg)
n-butylisocyanide
(0.5mmol-53uL)
N
181-56
Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
Furfurylamine
(0.5mmol-44.2uL)
2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
n-butylisocyanide
(0.5mmol-53uL)
Reactants
Insoluble
181-57
Salicylaldehyde
(0.5mmol-53.3uL)
Methylamine
(0.5mmol-250uL)
Phenylpropynoic acid
(0.5mmol-73.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-59
o-tolualdehyde
(0.5mmol-57.8uL)
Methylamine
(0.5mmol-250uL)
4-hydroxybenzoic acid
(0.5mmol-69mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-60
Salicylaldehyde
(0.5mmol-53.3uL)
Furfurylamine
(0.5mmol-44.2uL)
Phenylpropynoic acid
(0.5mmol-73.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-61
2,4,6-trimethylbenzaldehyde -(spoilt)
(0.5mmol-73.8uL)

3-Chloroaniline
(0.5mmol-53uL)

alpha-hydroxyphenylacetic acid
(0.5mmol-76mg)

TOSMIC
(0.5mmol-97.6mg)

N/A
181-62
3,5-dimethoxybenzaldehyde
(0.5mmol-83.1mg)
Methylamine
(0.5mmol-250uL)
4-hydroxybenzoic acid
(0.5mmol-69mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-63
Salicylaldehyde
(0.5mmol-53.3uL)
Propylamine
(0.5mmol-41.1uL)
3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-64
3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
1-hexylamine
(0.5mmol-66ul)
3-Methyl-2-butenoic acid
(0.5mmol-50.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-65
3,5-dimethoxybenzaldehyde
(0.5mmol-83.1mg)
Benzylamine
(0.5mmol-54.6uL)
Quinic Acid
(0.5mmol-96.1mg)
t-butylisocyanide
(0.5mmol-57.5uL)
N
181-66
3-hydroxybenzaldehyde
(0.5mmol-61.0mg)
Methylamine
(0.5mmol-250uL)
2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-67
4-hydroxybenzaldehyde
(0.5mmol-61mg)
Furfurylamine
(0.5mmol-44.2uL)
3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-68
o-vanillin
(0.5mmol-76.0mg)
Methylamine
(0.5mmol-250uL)
3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-69
2-naphthaldehyde
(0.5mmol- 78.1mg)
Aniline
(0.5mmol-45.5uL)
2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
TOSMIC
(0.5mmol-97.6mg)
Reactants
Insoluble
181-70
o-tolualdehyde
(0.5mmol-57.8uL)
3-Chloroaniline
(0.5mmol-53uL)
1-Pyrenebutyric acid
(0.5mmol-144.1mg)
n-butylisocyanide
(0.5mmol-53uL)
Reactants
Insoluble
181-71
Benzaldehyde
(0.5mmol-50.8uL)
Benzylamine
(0.5mmol-54.6uL)
alpha-hydroxyphenylacetic acid
(0.5mmol-76mg)
TOSMIC
(0.5mmol-97.6mg)
Y No Ugi product
181-72
4-(trifluoromethyl)benzaldehyde
(0.5mmol-68.3uL)
Methylamine
(0.5mmol-250uL)
2,6-dihydroxybenzoic aicd.H2O
(0.5mmol-77.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-73
Benzaldehdye
(0.5mmol-50.8uL)
Methylamine
(0.5mmol-250uL)
Boc-Trp-OH
(0.5mmol-152.1mg)
t-butylisocyanide
(0.5mmol-57.5uL)
N
181-74
3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
Aniline
(0.5mmol-45.5uL)
3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
t-butylisocyanide
(0.5mmol-57.5uL)
N
181-75
Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
Furfurylamine
(0.5mmol-44.2uL)
alpha-hydroxyphenylacetic acid
(0.5mmol-76mg)
n-butylisocyanide
(0.5mmol-53uL)
N
181-76
3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
Propylamine
(0.5mmol-41.1uL)
diphenylaceitc acid
(0.5mmol-106.1mg)
n-butylisocyanide
(0.5mmol-53uL)
N
181-77
3-methoxybenzaldehyde
(0.5mmol-61uL)
5-Methylfurfurylamine
(0.5mmol-55.7uL)
2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
n-butylisocyanide
(0.5mmol-53uL)
Reactants
Insoluble
181-78
Salicylaldehyde
(0.5mmol-53.3uL)
1-hexylamine
(0.5mmol-66ul)
1-Pyrenebutyric acid
(0.5mmol-144.1mg)
t-butylisocyanide
(0.5mmol-57.5uL)
Reactants
Insoluble
181-79
Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
Furfurylamine
(0.5mmol-44.2uL)
2,4,6-trihydroxybenzoic acid
(0.5mmol-94mg)
t-butylisocyanide
(0.5mmol-57.5uL)
Reactants
Insoluble
181-80
3-methoxybenzaldehyde
(0.5mmol-61uL)
Aniline
(0.5mmol-45.5uL)
2,4,6-trihydroxybenzoic acid
(0.5mmol-94mg)
TOSMIC
(0.5mmol-97.6mg)
Y
181-81
2-naphthaldehyde
(0.5mmol- 78.1mg)
2-Chloroaniline
(0.5mmol-52.6uL)
3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
t-butylisocyanide
(0.5mmol-57.5uL)
Reactants
Insoluble
181-82
3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
Furfurylamine
(0.5mmol-44.2uL)
3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-83
Benzaldehye
(0.5mmol-50.8uL)
Aniline
(0.5mmol-45.5uL)
1-Pyrenebutyric acid
(0.5mmol-144.1mg)
n-butylisocyanide
(0.5mmol-53uL)
Reactants
Insoluble
181-84
3-methoxybenzaldehyde
(0.5mmol-61uL)
Benzylamine
(0.5mmol-54.6uL)
alpha-hydroxyphenylacetic acid
(0.5mmol-76mg)
n-butylisocyanide
(0.5mmol-53uL)
N
181-85
Salicylaldehyde
(0.5mmol-53.3uL)
3-Chloroaniline
(0.5mmol-53uL)
2,5-dimethoxyphenylacetic acid
(0.5mmol-98.1)
TOSMIC
(0.5mmol-97.6mg)
N
181-86
3-hydroxybenzaldehyde
(0.5mmol-61.0mg)
Methylamine
(0.5mmol-250uL)
4-hydroxybenzoic acid
(0.5mmol-69mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-87
2,4-dimethylbenzaldehyde
(0.5mmol-69.7uL)
Methylamine
(0.5mmol-250uL)
1-Pyrenebutyric acid
(0.5mmol-144.1mg)
t-butylisocyanide
(0.5mmol-57.5uL)
Reactants
Insoluble
181-88
3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
5-Methylfurfurylamine
(0.5mmol-55.7uL)
diphenylaceitc acid
(0.5mmol-106.1mg)
n-butylisocyanide
(0.5mmol-53uL)
N
181-89
Salicylaldehyde
(0.5mmol-53.3uL)
3-Chloroaniline
(0.5mmol-53uL)
hexanoic acid
(0.5mmol-62.6uL)
TOSMIC
(0.5mmol-97.6mg)
Reactants
Insoluble
181-90
3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
Methylamine
(0.5mmol-250uL)
4-Nitrobenzoic acid
(0.5mmol-83.5mg)
TOSMIC
(0.5mmol-97.6mg)
Reactants
Insoluble
181-91
2-chloro-6-methylbenzaldehyde-(unavailable)
(05.mmol-77.3mg)
Methylamine
(0.5mmol-250uL)
Boc-Trp-OH
(0.5mmol-152.1mg)
n-butylisocyanide
(0.5mmol-53uL)
N/A
181-92
3-methoxybenzaldehyde
(0.5mmol-61uL)
2-Chloroaniline
(0.5mmol-52.6uL)
Decanoic acid
(0.5mmol-96.5uL)
TOSMIC
(0.5mmol-97.6mg)
N
181-93
Salicylaldehyde
(0.5mmol-53.3uL)
Aniline
(0.5mmol-45.5uL)
hexanoic acid
(0.5mmol-62.6uL)
TOSMIC
(0.5mmol-97.6mg)
N
181-94
3,5-dimethoxybenzaldehyde
(0.5mmol-83.1mg)
Furfurylamine
(0.5mmol-44.2uL)
3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-95
2-chloro-6-methylbenzaldehyde-(unavailable)
(05.mmol-77.3mg)
3-Chloroaniline
(0.5mmol-53uL)
alpha-hydroxyphenylacetic acid
(0.5mmol-76mg)
TOSMIC
(0.5mmol-97.6mg)
N/A
181-96
3-methoxybenzaldehyde
(0.5mmol-61uL)
Methylamine
(0.5mmol-250uL)
4-hydroxybenzoic acid
(0.5mmol-69mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-97
Salicylaldehyde
(0.5mmol-53.3uL)
Furfurylamine
(0.5mmol-44.2uL)
3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-98
4-hydroxybenzaldehyde
(0.5mmol-61mg)
Methylamine
(0.5mmol-250uL)
2,3-dihydroxybenzoic acid.
(0.5mmol-77.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-99
4-methoxybenzaldehyde
(0.5mmol-60.8uL)
2-Chloroaniline
(0.5mmol-52.6uL)
4-hydroxybenzoic acid
(0.5mmol-69mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-100
4-chlorobenzaldehyde
(0.5mmol-70.3mg)
Methylamine
(0.5mmol-250uL)
Quinic Acid
(0.5mmol-96.1mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-101
4,7-dimethoxy-1-naphthaldehyde
(0.5mmol-108.1mg)
Methylamine
(0.5mmol-250uL)
2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
TOSMIC
(0.5mmol-97.6mg)
Reactants
Insoluble
181-102
3-hydroxybenzaldehyde
(0.5mmol-61.0mg)
5-Methylfurfurylamine
(0.5mmol-55.7uL)
3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-103
Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
Methylamine
(0.5mmol-250uL)
alpha-hydroxyphenylacetic acid
(0.5mmol-76mg)
n-butylisocyanide
(0.5mmol-53uL)
N
181-104
4-(Dimethylamino)benzaldehyde
(0.5mmol-74.6mg)
Methylamine
(0.5mmol-250uL)
Quinic Acid
(0.5mmol-96.1mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-105
3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
t-butylamine
(05mmol-52.5uL)
4-chlorophenylacetic acid
(0.5mmol-85.3mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-106
2-naphthaldehyde
(0.5mmol- 78.1mg)
Methylamine
(0.5mmol-250uL)
4-hydroxybenzoic acid
(0.5mmol-69mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-107
Salicylaldehyde
(0.5mmol-53.3uL)
Aniline
(0.5mmol-45.5uL)
Phenylpropynoic acid
(0.5mmol-73.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-108
2-naphthaldehyde
(0.5mmol- 78.1mg)
Methylamine
(0.5mmol-250uL)
Quinic Acid
(0.5mmol-96.1mg)
TOSMIC
(0.5mmol-97.6mg)
Y No Ugi product
181-109
3-methoxybenzaldehyde
(0.5mmol-61uL)
1-hexylamine
(0.5mmol-66ul)
4-hydroxybenzoic acid
(0.5mmol-69mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-110
Salicylaldehyde
(0.5mmol-53.3uL)
Aniline
(0.5mmol-45.5uL)
3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-111
Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
Methylamine
(0.5mmol-250uL)
2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
t-butylisocyanide
(0.5mmol-57.5uL)
Reactants
Insoluble
181-112
4-methoxybenzaldehyde
(0.5mmol-60.8uL)
Methylamine
(0.5mmol-250uL)
2,3-dihydroxybenzoic acid
(0.5mmol-77.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-113
Veratraldehyde
(0.5mmol-83.1mg)
3-Chloroaniline
(0.5mmol-53uL)
3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-114
Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
5-Methylfurfurylamine
(0.5mmol-55.7uL)
2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
n-butylisocyanide
(0.5mmol-53uL)
Reactants
Insoluble
181-115
2-naphthaldehyde
(0.5mmol- 78.1mg)
3-Chloroaniline
(0.5mmol-53uL)
3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
t-butylisocyanide
(0.5mmol-57.5uL)
Reactants
Insoluble
181-116
4-chlorobenzaldehyde
(0.5mmol-70.3mg)
Methylamine
(0.5mmol-250uL)
2,3-dihydroxybenzoic acid
(0.5mmol-77.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-117
Veratraldehyde
(0.5mmol-83.1mg)
Furfurylamine
(0.5mmol-44.2uL)
2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
TOSMIC
(0.5mmol-97.6mg)
Reactants
Insoluble
181-118
5-bromo-2-thiophenecarboxaldehyde (0.5mmol-59.4uL)
Methylamine
(0.5mmol-250uL)
3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
TOSMIC
(0.5mmol-97.6mg)
N
181-119
3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
Methylamine
(0.5mmol-250uL)
diphenylaceitc acid
(0.5mmol-106.1mg)
n-butylisocyanide
(0.5mmol-53uL)
N
181-120
3,5-Bis(trifluoromethyl)benzaldehyde
(0.5mmol-121.0mg-??)
Methylamine
(0.5mmol-250uL)
2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
TOSMIC (0.5mmol-97.6mg)
N
181-121
3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
3-Chloroaniline
(0.5mmol-53uL)
4-chlorophenylacetic acid
(0.5mmol-85.3mg)
TOSMIC (0.5mmol-97.6mg)
N
181-122
Veratraldehyde
(0.5mmol-83.1mg)
2-Chloroaniline
(0.5mmol-52.6uL)
4-hydroxybenzoic acid
(0.5mmol-69mg)
TOSMIC (0.5mmol-97.6mg)
N
181-123
Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
Furfurylamine
(0.5mmol-44.2uL)
3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
TOSMIC (0.5mmol-97.6mg)
N
181-124
Salicylaldehyde
(0.5mmol-53.3uL)
Benzylamine
(0.5mmol-54.6uL)
3-(4-Methoxyphenyl)propionic acid (0.5mmol-90.1mg
TOSMIC (0.5mmol-97.6mg)
N

Results

Exp ID
Day1
Day-3
Final
Analytical data
181-55
181-55day1.JPG
181-55day3.JPG


181-56
181-56day1.JPG
181-56day3.JPG

Reactants
Insoluble
181-57
181-57day1.JPG
181-57day3.JPG


181-59
181-59day1.JPG
181-59day3.JPG


181-60
181-60day1.JPG
181-60day3.JPG


181-62
181-62day1.JPG
181-62day3.JPG


181-63
181-63day1.JPG
181-63day3.JPG


181-64
181-64day1.JPG
181-64day3.JPG


181-65
181-65day1.JPG
181-65day3.JPG


181-66
181-66day1.JPG
181-66day3.JPG


181-67
181-67day1.JPG
181-67day3.JPG


181-68
181-68day1.JPG
181-68day3.JPG


181-69
181-69day1.JPG
181-69day3.JPG

Reactants
Insoluble
181-70
181-70day1.JPG
181-70day3.JPG

Reactants
Insoluble
181-71
181-71day1.JPG
Day 1
181-71day3.JPG
Day 3
181-71day12.JPG
Day 12
Amount: 46mg
Yield:
M.P : 169-171C
IR
HNMR
CNMR
FAB-MS
181-72
181-72day1.JPG
181-72day3.JPG


181-73
181-73day1.JPG
181-73day3.JPG


181-74
181-74day1.JPG
181-74day3.JPG


181-75
181-75day1.JPG
181-75day3.JPG


181-76
181-76day1.JPG
181-76day3.JPG


181-77
181-77day1.JPG
181-77day3.JPG

Reactants
Insoluble
181-78
181-78day1.JPG
181-78day3.JPG

Reactants
Insoluble
181-79
181-79day1.JPG
181-79day3.JPG

Reactants
Insoluble
181-80
181-80day1.JPG
181-80day3.JPG

HNMR
CNMR
IR
FAB-MS
Crystal Structure
181-81
181-81day1.JPG
181-81day3.JPG

Reactants
Insoluble
181-82
181-82day1.JPG
181-82day3.JPG


181-83
181-83day1.JPG
181-83day3.JPG

Reactants
Insoluble
181-84
181-84day1.JPG
181-84day3.JPG


181-85
181-85day1.JPG
181-85day3.JPG


181-86
181-86day1.JPG
181-86day3.JPG


181-87
181-87day1.JPG
181-87day3.JPG

Reactants
Insoluble
181-88
181-88day1.JPG
181-88day3.JPG


181-89
181-89day1.JPG
181-89day3.JPG


181-90
181-90day1.JPG
181-90day3.JPG

Reactants
Insoluble
181-92
181-92day1.JPG
181-92day3.JPG


181-93
181-93day1.JPG
181-93day3.JPG


181-94
181-94day1.JPG
181-94day3.JPG


181-96
181-96day1.JPG
181-96day3.JPG


181-97
181-97day1.JPG
181-97day3.JPG


181-98
181-98day1.JPG
181-98day3.JPG


181-99
181-99day1.JPG
181-99day3.JPG


181-100
181-100day1.JPG
181-100day3.JPG

Reactants
Insoluble
181-101
181-101day1.JPG
181-101day3.JPG

Reactants
Insoluble
181-102
181-102day1.JPG
181-102day3.JPG


181-103
181-103day1.JPG
181-103day3.JPG


181-104
181-104day1.JPG
181-104day3.JPG


181-105
181-105day1.JPG
181-105day3.JPG


181-106
181-106day1.JPG
181-106day3.JPG


181-107
181-107day1.JPG
181-107day3.JPG


181-108
181-108day1.JPG
Day 1
181-108day3.JPG
Day 3
181-108day12.JPG
Day 12
Amount: 16mg -
Isoluble in DMSO-D6
Yield
M.P: 203-205C
IR
FAB-MS
181-109
181-109day1.JPG
181-109day3.JPG


181-110
181-110day1.JPG
181-110day3.JPG


181-111
181-111day1.JPG
181-111day3.JPG

Reactants
Insoluble
181-112
181-112day1.JPG
181-112day3.JPG


181-113
181-113day1.JPG
181-113day3.JPG


181-114
181-114day1.JPG
181-114day3.JPG

Reactants
Insoluble
181-115
181-115day1.JPG
181-115day3.JPG

Reactants
Insoluble
181-116
181-116day1.JPG
181-116day3.JPG


181-117
181-117day1.JPG
181-117day3.JPG

Reactants
Insoluble
181-118
181-118day1.JPG
181-118day1.JPG


181-119
181-119day1.JPG
181-119day1.JPG


181-120
181-120day1.JPG
181-120day1.JPG


181-121
181-121day1.JPG
181-121day1.JPG


181-122
181-122day1.JPG
181-122day1.JPG


181-123
181-123day1.JPG
181-123day1.JPG


181-124
181-124day1.JPG
181-124day1.JPG



Discussion

181-71 From the HNMR of the sample it is obvious that the solid obtained is not a clean ugi product, if at all. Similarly 181-108, the FAB MS shows no peaks corresponding to a ugi product. It is beyond the scope of this project to isolate or determine the nautre of these compounds.

Conclusions

No Ugi products isolated from this experiment.

Log

2008-04-09
13:00 Made up a solution of each aldehyde in methanol in vials labelled with Exp-Rank number. 2ml of methanol was used in vials which did not use methyl amine (in methanol solution). Vials which used methyl amine as the amine component used only 1850uL of methanol. Each vial was vortexed for 30s. Phenanthrene-9-Carboxaldehyde (181-55,56,75,79,103,111,114,123) and 4,7-dimethoxy-1-naphthaldehyde (181-101) did not go in solution.
Weights of dry,empty vials with labels and no cap-
181-055- 4.7012g
181-056- 4.6561g
181-057- 4.6500g
181-059- 4.6503g
181-060- 4.6620g
181-061- 4.6585g
181-062- 4.6755g
181-063- 4.7131g
181-064- 4.7336g
181-065- 4.6360g
181-066- 4.6888g
181-067- 4.6888g
181-068- 4.6744g
181-069- 4.6813g
181-070- 4.6575g
181-071- 4.6683g
181-072- 4.6789g
181-073- 4.6613g
181-074- 4.6420g
181-075- 4.6650g
181-076- 4.6905g
181-077- 4.6530g
181-078- 4.6733g
181-079- 4.6621g
181-080- 4.6685g
181-081- 4.6540g
181-082- 4.6532g
181-083- 4.6900g
181-084- 4.6943g
181-085- 4.6545g
181-086- 4.6466g
181-087- 4.6879g
181-088- 4.6700g
181-089- 4.6788g
181-090- 4.6638g
181-092- 4.6990g
181-093- 4.6676g
181-094- 4.6493g
181-096- 4.6820g
181-097- 4.6760g
181-098- 4.6610g
181-099- 4.6677g
181-100- 4.6600g
181-101- 4.6686g
181-102- 4.6785g
181-103- 4.6673g
181-104- 4.6729g
181-105- 4.6545g
181-106- 4.6545g
181-107- 4.6795g
181-108- 4.6786g
181-109- 4.6900g
181-110- 4.6700g
181-111- 4.6675g
181-112- 4.6415g
181-113- 4.6558g
181-114- 4.6785g
181-115- 4.6902g
181-116- 4.6684g
181-117- 4.6600g
181-118- 4.6712g
181-119- 4.6530g
181-120- 4.6618g
181-121- 4.6700g
181-122- 4.6655g
181-123- 4.6560g
181-124- 4.6948g
15:30 Added respective amines to each vial. Vortexed for 30s.
2008-04-10
23:00 Completed addition of respective acids to each vial. The vials were vortexed for 30s each after the acid addition.
2008-04-14
22:30 Completed addition of respective isocyanides to each vial. The vials were vortexed for 30s each after the isocyanide addition; obtained picture of the vials -(Day-1 series)
2008-04-16
16:50 Obtained pictures of the vials-(Day-3 series)
2008-04-23
11:45 Vortexed vial containing solutions 181-055 -181-124 for 15s each. Solution number 181-100 previously reported as 'reactants insoluble' has now turned clear.
2008-04-25
10:00 Observed solid in vials 181-71 and 181-108; obtained pictures.
2008-04-30
14:00 Vortexed 181-71 and 181-108 for 30s each, centrifuged them for 1min and decanted the supernatant. The residue was washed with methanol (3x 1000uL) each time vortexing the solution for 30s and centrifuging for 1min before decanting the supernatant.
15:45 The residues from 181-71 and 181-108 were set on high vac.
18:45 Removed them from high vac and obtained the now renamed 181-71A (46 mg) and 181-108A (16 mg)

Tags

Chemical
Inchi
Inchikey
benzaldehyde
InChI=1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H
HUMNYLRZRPPJDN-UHFFFAOYAE
3-methoxybenzaldehyde
InChI=1/C8H8O2/c1-10-8-4-2-3-7(5-8)6-9/h2-6H,1H3/i1-12,2-12,3-12,4-12,5-12,6-12,7-12,8-12,9-16,10-16
WMPDAIZRQDCGFH-UHFFFAOYAC
Phenanthrene-9-carboxaldehyde
InChI=1/C15H10O/c16-10-12-9-11-5-1-2-6-13(11)15-8-4-3-7-14(12)15/h1-10H
QECIGCMPORCORE-UHFFFAOYAE
Salicylaldehyde
InChI=1/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H
SMQUZDBALVYZAC-UHFFFAOYAD
3,4-dimethoxybenzaldehyde
InChI=1/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3
WJUFSDZVCOTFON-UHFFFAOYAT
4-methylbenzaldehyde
InChI=1/C8H8O/c1-7-2-4-8(6-9)5-3-7/h2-6H,1H3/i1-12,2-12,3-12,4-12,5-12,6-12,7-12,8-12,9-16

2-naphthaldehyde
InChI=1/C11H8O/c12-8-9-5-6-10-3-1-2-4-11(10)7-9/h1-8H
PJKVFARRVXDXAD-UHFFFAOYAM
2,3-dihydroxybenzaldehyde
InChI=1/C7H6O3/c8-4-5-2-1-3-6(9)7(5)10/h1-4,9-10H
IXWOUPGDGMCKGT-UHFFFAOYAD
4-chlorobenzaldehyde
InChI=1/C7H5ClO/c8-7-3-1-6(5-9)2-4-7/h1-5H
AVPYQKSLYISFPO-UHFFFAOYAQ
4-methoxybenzaldehyde
InChI=1/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3
ZRSNZINYAWTAHE-UHFFFAOYAA
3,4-dihydroxybenzaldehyde
nChI=1/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H
IBGBGRVKPALMCQ-UHFFFAOYAN
3-hydoxybenzaldehyde
InChI=1/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H
IAVREABSGIHHMO-UHFFFAOYAC
3,5-dimethoxybenzaldehyde
InChI=1/C9H10O3/c1-11-8-3-7(6-10)4-9(5-8)12-2/h3-6H,1-2H3
VFZRZRDOXPRTSC-UHFFFAOYAG
4,7-Dimethoxy-1-naphthaldehyde
InChI=1/C13H12O3/c1-15-10-4-5-11-12(7-10)9(8-14)3-6-13(11)16-2/h3-8H,1-2H3
FFAODEUKHYBIKI-UHFFFAOYAI
5-methylfurfurylamine
InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3
YSEAGSCGERFGBL-UHFFFAOYAH
furfurylamine
InChI=1/C5H7NO/c6-4-5-2-1-3-fu7-5/h1-3H,4,6H2c
DDRPCXLAQZKBJP-UHFFFAOYAX
methylamine
InChI=1/CH5N/c1-2/h2H2,1H3
BAVYZALUXZFZLV-UHFFFAOYAN
n-propylamine
InChI=1/C3H9N/c1-2-3-4/h2-4H2,1H3
WGYKZJWCGVVSQN-UHFFFAOYAG
aniline
InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
PAYRUJLWNCNPSJ-UHFFFAOYAP
3-chloroaniline
InChI=1/C6H6ClN/c7-5-2-1-3-6(8)4-5/h1-4H,8H2/i1-12,2-12,3-12,4-12,5-12,6-12,7-35,8-14

3,4-dihydroxyphenylacetiacid
InChI=1/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
CFFZDZCDUFSOFZ-UHFFFAOYAU
5-nitrosalicylic acid
InChI=1/C7H5NO5/c9-6-2-1-4(8(12)13)3-5(6)7(10)11/h1-3,9H,(H,10,11)
PPDRLQLKHRZIJC-UHFFFAOYAT
benzoic acid
InChI=1/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
WPYMKLBDIGXBTP-UHFFFAOYAD
Boc-L-tryptophan
InChI=1/C1 ​6H20N2O4/c​1-16(2,3)2​2-15(21)18​-13(14(19)​20)8-10-9-​17-12-7-5-​ 4-6-11(10)​12/h4-7,9,​13,17H,8H2​,1-3H3,(H,​18,21)(H,1​9,20)
NFVNYBJCJGKVQK-UHFFFAOYAR
2,4,6-trihydroxybenzoicacid
InChI=1/C7H6O5/c8-3-1-4(9)6(7(11)12)5(10)2-3/h1-2,8-10H,(H,11,12)
IBHWREHFNDMRPR-UHFFFAOYAP
2-methylpropeneoicacid
InChI=1/C4H6O2/c1-3(2)4(5)6/h1H2,2H3,(H,5,6)
CERQOIWHTDAKMF-UHFFFAOYAE
(±)-2-Phenylbutanoic acid
InChI=1/C10H12O2/c1-2-9(10(11)12)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,11,12)
OFJWFSNDPCAWDK-UHFFFAOYAE
D-(−)-Quinic acid
InChI=1/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5?,7?/m1/s1
AAWZDTNXLSGCEK-LNVDRNJUBH
n-butanoic acid
InChI=1/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
FERIUCNNQQJTOY-UHFFFAOYAP
Mandelic acid
InChI=1/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1
IWYDHOAUDWTVEP-ZETCQYMHBP
2-Hydroxy-5-nitrobenzoicacid
InChI=1/C7H5NO5/c9-6-2-1-4(8(12)13)3-5(6)7(10)11/h1-3,9H,(H,10,11)
PPDRLQLKHRZIJC-UHFFFAOYAT
(2,5-Dimethoxyphenyl)acetic acid
InChI=1/C10H12O4/c1-13-8-3-4-9(14-2)7(5-8)6-10(11)12/h3-5H,6H2,1-2H3,(H,11,12)
BBZDYQUXRFATHZ-UHFFFAOYAX
TOSMIC
InChI=1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3
CFOAUYCPAUGDFF-UHFFFAOYA
n-butylisocyanide
InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3
FSBLVBBRXSCOKU-UHFFFAOYAR
t-butylisocyanide
InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3
FAGLEPBREOXSAC-UHFFFAOYAL
4-hydroxybenzoic acid
InChI=1/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)
FJKROLUGYXJWQN-UHFFFAOYAQ
2,5-dimethoxyphenylacetic acid
InChI=1/C10H12O4/c1-13-8-3-4-9(14-2)7(5-8)6-10(11)12/h3-5H,6H2,1-2H3,(H,11,12)
BBZDYQUXRFATHZ-UHFFFAOYAX
diphenylacetic acid
InChI=1/C14H12O2/c15-14(16)13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13H,(H,15,16)
PYHXGXCGESYPCW-UHFFFAOYAC
3-methylbut-2-enoic acid
InChI=1/C5H8O2/c1-4(2)3-5(6)7/h3H,1-2H3,(H,6,7)
YYPNJNDODFVZLE-UHFFFAOYAX
2,6-dihydroxybenzoic aicd
InChI=1/C7H6O4/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3,8-9H,(H,10,11)
AKEUNCKRJATALU-UHFFFAOYAG
Phenylpropynoic acid
InChI=1/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11)
XNERWVPQCYSMLC-UHFFFAOYAX
1-hexylamine
InChI=1/C6H15N/c1-2-3-4-5-6-7/h2-7H2,1H3
BMVXCPBXGZKUPN-UHFFFAOYAQ
Benzylamine
InChI=1/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2
WGQKYBSKWIADBV-UHFFFAOYAL
3-hydroxybenzaldehyde
InChI=1/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H
IAVREABSGIHHMO-UHFFFAOYAC
2,4,6-trimethylbenzaldehyde
InChI=1/C10H12O/c1-7-4-8(2)10(6-11)9(3)5-7/h4-6H,1-3H3/i1-12,2-12,3-12,4-12,5-12,6-12,7-12,8-12,9-12,1-12,11-16

2-methylbenzaldehyde
InChI=1/C8H8O/c1-7-4-2-3-5-8(7)6-9/h2-6H,1H3/i1-12,2-12,3-12,4-12,5-12,6-12,7-12,8-12,9-16

2-Hydroxybenzaldehyde
InChI=1/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H
SMQUZDBALVYZAC-UHFFFAOYAD