exp169a.gif

Objective

To synthesize a Ugi product (incorrect) following the EXPLAN005 by using Phenanthrene-9-carboxaldehyde , tert-butylisocyanide, cyclohexylamine, and 3,4-methylenedioxyphenylacetic acid. The compound will contribute towards a library for Falcipain2 inhibitors.This compunds was ranked 23 in the DEXP014-V1B file from D-EXP014 .

Procedure

As described in Explan005

ID/ Lib Rank
Solvent
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
169/23
Methanol
Phenanthrene-9-
carboxaldehyde
cyclohexylamine
3,4 methylenedioxyphenylacetic acid
tert-butylisocyanide
N/A
Quantity
1000uL
0.5mmol, 103.1mg
0.5mmol, 57.2uL
(density=0.867g/ml)
0.5mmol, 90.08 mgexternal image insert_table.gif
0.5mmol, 56.5uL
(density=0.735g/ml)


Density information found on the Ugi Chemicals page.

Results

Photos taken directly after all the components were charged and vortexed.
Exp169.jpg
169A (after mixing)

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

Discussion

All results are recorded Master Table and Workflow Tables

Conclusion

Experiment aborted because a clear solution was never obtained.

Log

2008-02-07

12:23- Added methanol to one dram vial.
12:26- Added amine to vial and vortexed for 15 seconds.
12:28- Added aldehyde to vial and vortexed for 10 minutes. No clear solution was obtained.
12:40-Added acid to vial and vortexed for 10 mintues. Very difficult to achieve solution, no solution was obtained.
12:52- Added isocyanide to vial and vortexed for 10 minutes. No solution was obtained.
1:02- Picture 169A was taken.

Tags

Phenanthrene-9-carboxaldehydeInChI=1/C15H10O/c16-10-12-9-11-5-1-2-6-13(11)15-8-4-3-7-14(12)15/h1-10HInChIKey QECIGCMPORCORE-UHFFFAOYAE
tert-butylisocyanideInChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3 InChIKey FAGLEPBREOXSAC-UHFFFAOYAL
cyclohexylamineInChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2InChIKeyIFYLVUHLOOCYBG-UHFFFAOYAD
3,4-methylenedioxyphenylacetic acid InChI=1/C9H8O4/c10-9(11)4-6-1-2-7-8(3-6)13-5-12-7/h1-3H,4-5H2,(H,10,11) InChIKeyODVLMCWNGKLROU-UHFFFAOYAB
Ugi Product InChI=1/C3 ​4H38N2O2/c​1-34(2,3)3​5-33(38)32​(30-23-25-​16-10-11-1​9-27(25)28​ -20-12-13-​21-29(28)3​0)36(26-17​-8-5-9-18-​26)31(37)2​2-24-14-6-​ 4-7-15-24/​h4,6-7,10-​16,19-21,2​3,26,32H,5​,8-9,17-18​,22H2,1-3H​ 3,(H,35,38​) InChIKeyNYDTYYMZLJAMKH-UHFFFAOYAI (incorrect)