Exp137

=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] [|benzylamine][|InChI=1/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2] [|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] [|propylamine][|InChI=1/C3H9N/c1-2-3-4/h2-4H2,1H3] [|t-butylisocyanide][|InChI=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 acid][|InChI=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-chloroaniline][|InChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2] [|cyclohexylamine][|InChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2] [|aniline][|InChI=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]