Exp_177_Rxn_Scheme.JPG
Reaction Scheme


Objective

To synthesize a Ugi Product following the EXPLAN005 . The compound will contribute towards a library for Falcipain2 inhibitors.
This compounds was ranked 38 in the DEXP014-V1B 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

As described in Explan005
This reaction used Phenanthrene-9-carboxaldehyde, propylamine, n-butyl isocyanide and phenylacetic acid.
Phenanthrene-9-Carboxaldehyde (solid from Sigma-Aldrich)
HNMR
ID/ Lib Rank
Solvent
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
177/38
Methanol
Phenanthrene-9-
carboxaldehyde
propylamine
Phenylacetic acid
n-butylisocyanide
N/A
Quantity
2000uL
0.5mmol, 103.1mg
0.5mmol, 41.1uL
(density=0.719g/ml)
0.5mmol, 68.1mg
0.5mmol, 52.3uL
(density=0.795g/ml)


Density information found on the Ugi Chemicals Page in Left Navigation Bar.

Results

Photos taken directly after all the components were charged and vortexed.
rank_38.JPG
177A


All results are recorded Master Table and Workflow Tables .


Discussion

No dissolution could be achieved during the additions even with 30 minutes of vortexing as well as further dilution.

Conclusion

Experiment aborted because a clear solution was never obtained immediately after mixing all reagents or the addition of extra solvent. A further discussion of the apparent amine selective solubility of phenanthrene-9-carboxaldehyde is presented here.

Log

2008-02-28

15:46- Weighed out the Phenanthrene-9-carboxaldehyde.
15:52- Weighed out the phenylacetic acid.
15:55- Charged a vial with 1000 ul of methanol.
16:04- Added the propylamine to the vial.
16:05 Vortexed vial 1 min
16:06- Added the phenanthrene-9-carboxaldehyde.
16:07-Vortexed vial 1 min
16:08- Added the phenylacetic acid.
16:09-Vortexed vial 1 min, did not dissolve, moved on to next addition
16:10- Added the n-butyl isocyanide.
16:11-Vortexed 5 min, still no dissolution, made decision to add methanol to dilute it.
16:16-Added extra 500ul of methanol
16:17-Vortexed 5 min, still no dissolution
16:22-Added another 500ul of methanol
16:23-Vortexed 5 min, no change in solubility
16:28-Concluded that no further dissolution possible.
16:35- A photo was taken (177A) to demonstrate insolubility.

Tags

propylamine InChI=1/C3H9N/c1-2-3-4/h2-4H2,1H3 InChIKey WGYKZJWCGVVSQN-UHFFFAOYAG
Phenanthrene-9-carboxaldehydeInChI=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
phenylacetic acid InChI=1/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3 WLJVXDMOQOGPHL-UHFFFAOYAR
n-butyl isocyanide InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3 InChIKey: FSBLVBBRXSCOKU-UHFFFAOYAR
Ugi Product InChI=1/C3 ​1H34N2O2/c​1-3-5-19-3​2-31(35)30​(33(20-4-2​)29(34)21-​23-13-7-6-​ 8-14-23)28​-22-24-15-​9-10-16-25​(24)26-17-​11-12-18-2​7(26)28/h6​ -18,22,30H​,3-5,19-21​H2,1-2H3,(​H,32,35) InChIKey: JNSYWEITXVHUPZ-UHFFFAOYAJ