Objective

To synthesize 2 Ugi products following the EXPLAN005 . The compound will contribute towards a library for Falcipain2 inhibitors. These compunds were ranked 204 and 205 in the DEXP014-V1B file from D-EXP014.

Procedure

As described in Explan005
Two Ugi reactions were carried out in 1 dram vials labeled 1and 2. Vial 1 contained Phenanthrene-9-carboxaldehyde (0.25mmol, 51.6mg), t-butylamine(0.25mmol, 24.6uL), Phenylacetic Acid(0.25mmol, 34.0mg), and Tosylmethyl isocyanide (0.25mmol, 38.8mg), added in that order. Vial 2 contained 2-furaldehyde (0.25mmol, 30.5mg), Furfurylamine (0.25mmol, 27.4uL), 2,3 dihydroxybenzoic acid(0.25mmol, 38.5mg), and Tosylmethyl isocyanide (0.25mmol, 38.8mg), added in that order. After each addition, the solution was vortexed for 15s and made sure a homogeneous solution was obtained. The formation or absence of precipitate was noted. The dram vials were left at room temperature.
Comp ID/ Lib Rank
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
146-1/204
Phenanthrene-9-carboxaldehyde (0.25mmol, 51.6mg)
t-butylamine(0.25mmol, 24.6uL)
Phenylacetic Acid(0.25mmol, 34.0mg)
Tosylmethyl isocyanide (0.25mmol, 38.8mg)
No
146-2/205
2-furaldehyde (0.25mmol, 30.5mg)
Furfurylamine (0.25mmol, 27.4uL)
2,3 dihydroxybenzoic acid(0.25mmol, 38.5mg)
Tosylmethyl isocyanide (0.25mmol, 38.8mg)
No


Results

All results are recorded in the Master Table of all Ugi synthesis attempts

Discussion


Conclusion

Experiment aborted - no results provided.

Log

2007-11-16

15:47: Weighed out phenylacetic acid, tosylmethyl isocyanide, phenanthrene-9-carboxaldehyde, 2-furaldehyde, and 2,3-dihydroxybenzoic acid on weighing paper
15:50: Added methanol (500uL) into the dram vials, followed by 15 seconds vortexing.
15:52: Added aldehyde into the dram vials, followed by 15 seconds vortexing.
15:55: Added amine into the dram vials, followed by 15 seconds vortexing.
15:58: Added acid into the dram vials followed by 15 seconds vortexing
16:02: Added isocyanide into dram vials followed by 15 seconds vortexing
16:04: Vials were kept in hood overnight

2007-11-19

15:38: Vials were looked at and determined to have no precipitate
next chance you have take a pic - remember to vortex first

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/h1-10H
tosylmethylisocyanide InChI=1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3
t-butylamine InChI=1/C4H11N/c1-4(2,3)5/h5H2,1-3H3
phenylacetic acid InChI=1/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3
2-furaldehyde InChI=1/C5H4O2/c6-4-5-2-1-3-7-5/h1-4H
furfurylamine InChI=1/C5H7NO/c6-4-5-2-1-3-7-5/h1-3H,4,6H2