Objective

To synthesize eight Ugi products following the EXPLAN005 . The compound will contribute toward a library for Falcipain2 inhibitors.
These compunds were ranked 2-9 in the DEXP014-V1B

Procedure

Eight Ugi reactions were carried out in 1 dram vials labeled 1, 2, 3, 4, 5, 6, 7, and 8. Vial 1 contained methanol (500uL), phenanthrene-9-carboxaldehyde (0.25mmol, 42.4uL), propylamine (0.25mmol, 20.4uL), 4-chlorophenyl acetic acid (0.25mmol, 42.65mg), and n-butylisocyanide (0.25mmol, 26.1uL), added in that order. Vial 2 contained methanol (500uL), phenanthrene-9-carboxaldehyde (0.25mmol, 42.4uL), propylamine (0.25mmol, 20.4uL), 3,4-hydroxyphenylacetic acid (0.25mmol, 152.1mg), and n-butylisocyanide (0.25mmol, 26.1uL), added in that order. Vial 3 contained methanol (500 uL), phenanthrene-9-carboxaldehyde (0.25mmol, 42.04g), furfurylamine (0.25mmol, 22.1uL), 4-chlorophenyl acetic acid (0.25mmol, 42.65mg), and n-butylisocyanide (0.25mmol, 26.1uL) added in that order. Vial 4 contained phenanthrene-9-carboxaldehyde (0.25mmol, 42.4uL), aniline (0.25mmol, 22.8uL), 4-chlorophenyl acetic acid (0.25mmol, 42.65mg), and n-butylisocyanide (0.25mmol, 26.1uL), added in that order. Vial 5 contained phenanthrene-9-carboxaldehyde (0.25mmol, 42.4uL), 2-chloroaniline (0.25mmol, 25.9uL), 4-chlorophenyl acetic acid (0.25mmol, 42.65mg), and n-butylisocyanide (0.25mmol, 26.1uL), added in that order. Vial 6 contained phenanthrene-9-carboxaldehyde (0.25mmol, 42.4uL), hexylamine (0.25mmol, 32.8 uL), crotonic acid (0.5mmol, 21.52mg), and n-butylisocyanide (0.25mmol, 26.1uL), added in that order. Vial 7 contained phenanthrene-9-carboxaldehyde (0.25mmol, 42.4uL), cyclohexylamine (0.25mmol, 28.5uL), 4-chlorophenyl acetic acid (0.25mmol, 42.65mg), and t-butylisocyanide (0.25mmol, 28.3uL), added in that order. Vial 8 contained phenanthrene-9-carboxaldehyde (0.25mmol, 42.4uL), benzylamine(0.25mmol, 27.4uL), furoic acid (0.25mmol, 28.02mg), and n-butylisocyanide (0.25mmol, 26.1uL), 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.

Results

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

Discussion


No precipitate or color change was observed in these samples. However, there is an important factor to make note of in this experiment. A bad sample of phenanthrene-9-carboxaldehyde was used in all 8 samples made in this experiment. As a result, no significant conclusions can be made for this experiment as many of these results may be different with a good sample of phenanthrene-9-carboxaldehyde. Repeated experimentation will be necessary for these compounds in the future.

Conclusion

Experiment aborted because of bad reagent and no results recorded.

Log

2007-10-17

16:50: Weighed out acids on weighing paper
17:05: Added methanol (500uL) into the dram vials, followed by 30 seconds vortexing.
17:10: Added aldehyde into the dram vials, followed by 15 seconds vortexing.
17:14: Added amine into the dram vials, followed by 30 second vortexing.
17:24: Added acid into the dram vials followed by 15 second vortexing
17:28: Added isocyanide into dram vials followed by 15 second vortexing.
17:32: Let vials sit in fume hoods tonight

2007-10-18

09:00: Found no precipitate in any of the dram vials any pics? did you try sonicating?

Tags

n-butylisocyanide InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3
hexylamine InChI=1/C6H15N/c1-2-3-4-5-6-7/h2-7H2,1H3
benzylamineInChI=1/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2
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
propylamineInChI=1/C3H9N/c1-2-3-4/h2-4H2,1H3
t-butylisocyanideInChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3
furfurylamine InChI=1/C5H7NO/c6-4-5-2-1-3-7-5/h1-3H,4,6H2
4-chlorophenyl acetic acidInChI=1/C8H7ClO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2,(H,10,11)/f/h10H
3,4-hydroxyphenylacetic acid InChI=1/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)/f/h11H
2-chloroanilineInChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2
cyclohexylamineInChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2
anilineInChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
furoic acid InChI=1/C5H4O3/c6-5(7)4-2-1-3-8-4/h1-3H,(H,6,7)
crotonic acid InChI=1/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/f/h5H