exp182.gif

Objective

To synthesize a Ugi Product following the EXPLAN005 with phenanthrene-9-carboxaldehyde, heptylamine, furoic acid acid and n-butyl isocyanide. The compound will contribute towards a library for Falcipain2 inhibitors.
This compounds was ranked 28 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, n-Heptylamine, n-butyl isocyanide and Furoic acid.
Phenanthrene-9-Carboxaldehyde (solid from Sigma-Aldrich)
HNMR
ID/ Lib Rank
Solvent
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
182/28
Methanol
Phenanthrene-9-
carboxaldehyde
heptylamine
Furoic acid
n-butylisocyanide
Reagents
Insoluble
Quantity
1000uL
0.5mmol, 103.1mg
0.5mmol, 74.1uL
(density=0.777g/ml)
0.5mmol, 56.04
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.
182A
Exp182A.JPG


Discussion



Conclusion

The starting materials are insoluble.

Log

2008-04-07

13:39- Charged a vial with 1000 ul of methanol.
13:42- Weighed out the Phenanthrene-9-carboxaldehyde.
13:45- Added the heptylamine to the vial.
13:48- Vortexed vial 15 seconds.
13:50- Added the phenanthrene-9-carboxaldehyde.
13:51- Vortexed vial 2 min. No clear solution was obtained.
13:55- Added the furoicic acid.
13:58- Vortexed vial 3 min. No clear solution was obtained.
14:03- Added the n-butyl isocyanide.
14:05- Vortexed 5 min. No clear solution was obtained.
14:12- A photo was taken (182A).


Tags

n-butyl isocyanide InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3 InChIKey: FSBLVBBRXSCOKU-UHFFFAOYAR
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 InChIKey: QECIGCMPORCORE-UHFFFAOYAE
n-Heptylamine : InChI=1/C7H17N/c1-2-3-4-5-6-7-8/h2-8H2,1H3 InChIKey: WJYIASZWHGOTOU-UHFFFAOYAD
Furoic acid InChI=1/C5H4O3/c6-5(7)4-2-1-3-8-4/h1-3H,(H,6,7) InChiKey: SMNDYUVBFMFKNZ-UHFFFAOYAH