EXP167

=Objective= To synthesize a [|Ugi Product] following the EXPLAN005. The compound will contribute towards a library for Falcipain2 inhibitors, [|summary post]. This compunds was ranked 12 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

carboxaldehyde || propylamine || 3,4-methylenedioxyphenyl acetic acid || n-butylisocyanide || aborted || (density=0.795g/ml) ||  ||
 * ID/ Lib Rank || Solvent || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt Yes/No ||
 * 138-2/12 || Methanol || Phenanthrene-9-
 * Quantity || 1000uL || 0.5mmol, 103.1mg || 0.5mmol, 41.1 ul || 0.5mmol, 90.08 mg || 0.5mmol, 52.28 uL

Density information found at the Ugi Chemicals page.

= = =Results= all components** (167A) ||  ||
 * **30 min after mixing

All results are recorded Master Table and Workflow Tables. =Discussion= =Conclusion= Experiment aborted since no homogenous solution was formed. The aldehyde is not very soluble in the solvent, and no clear solution was ever obtained after the aldehyde was added. The insolubility of the aldehyde posed problems in other experiments as well but in others it didn't. This may be because of the reaction that the amine and aldehyde undergo to form a imine. The phenathrene may amine specific, in order to go into solution.

=Log=

2008-01-29
13:05 Added methanol to vial 13:10 Added propylamine to the vial and vortexed for 15 seconds. 13:15 Added aldehyde to vial and vortexed for 15 seconds followed by sonication for 5 minutes. 13:20- Vial was vortexed for 5 minutes, no solution obtained. 13:30 - The acid was added to the vial and vortexed for 15 seconds. 13:31- The vial was vortexed for 5 minutes. 13:36- The vial was sonicated for 5 minutes. 13:44- The isocyanide was added. 13:45 The solution was vortexed for 15 seconds. 13:46 The solution was sonicated for 5 minutes. 13:51 The solution was vortexed for an additional 10 minutes, no solution was obtained. 14:15 Picture **167A** was taken.

=Tags= [|propylamine] [|InChI=1/C3H9N/c1-2-3-4/h2-4H2,1H3] InChIKey [|WGYKZJWCGVVSQN]-[|UHFFFAOYAG] [|n-butylisocyanide] [|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%2811%2915-8-4-3-7-14%2812%2915/h1-10H] InChIKey [|QECIGCMPORCORE]-[|UHFFFAOYAE] [|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] [|UgiProduct InChI=1/C32H34N2O4/c1-3-5-16-33-32(36)31(27-20-23-10-6-7-11-24(23)25-12-8-9-13-26(25)27)34(17-4-2)30(35)19-22-14-15-28-29(18-22)38-21-37-28/h6-15,18,20,31H,3-5,16-17,19,21H2,1-2H3,(H,33,36) InChIKey XZPSENWJJNOGKV-UHFFFAOYAP]