Exp177

==

=Objective= To synthesize a [|Ugi Product] following the EXPLAN005. The compound will contribute towards a library for Falcipain2 inhibitors. This compounds was ranked 38 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 This reaction used [|Phenanthrene-9-carboxaldehyde], [|propylamine], [|n-butyl isocyanide] and [|phenylacetic acid]. [|HNMR] carboxaldehyde || propylamine || Phenylacetic acid || n-butylisocyanide || N/A || (density=0.719g/ml) || 0.5mmol, 68.1mg || 0.5mmol, 52.3uL (density=0.795g/ml) ||  ||
 * Phenanthrene-9-Carboxaldehyde** (solid from Sigma-Aldrich)
 * ID/ Lib Rank || Solvent || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt Yes/No ||
 * 177/38 || Methanol || Phenanthrene-9-
 * Quantity || 2000uL || 0.5mmol, 103.1mg || 0.5mmol, 41.1uL

Density information found on the Ugi Chemicals Page in Left Navigation Bar.

=Results= Photos taken directly after all the components were charged and vortexed.

All results are recorded Master Table and Workflow Tables.

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

=Conclusion= Experiment aborted because a clear solution was never obtained immediately after mixing all reagents or the addition of extra solvent. A further discussion of the apparent amine selective solubility of phenanthrene-9-carboxaldehyde is presented here.

=Log=

2008-02-28
15:46- Weighed out the Phenanthrene-9-carboxaldehyde. 15:52- Weighed out the phenylacetic acid. 15:55- Charged a vial with 1000 ul of methanol. 16:04- Added the propylamine to the vial. 16:05 Vortexed vial 1 min 16:06- Added the phenanthrene-9-carboxaldehyde. 16:07-Vortexed vial 1 min 16:08- Added the phenylacetic acid. 16:09-Vortexed vial 1 min, did not dissolve, moved on to next addition 16:10- Added the n-butyl isocyanide. 16:11-Vortexed 5 min, still no dissolution, made decision to add methanol to dilute it. 16:16-Added extra 500ul of methanol 16:17-Vortexed 5 min, still no dissolution 16:22-Added another 500ul of methanol 16:23-Vortexed 5 min, no change in solubility 16:28-Concluded that no further dissolution possible. 16:35- A photo was taken (177A) to demonstrate insolubility.

=Tags= [|propylamine] [|InChI=1/C3H9N/c1-2-3-4/h2-4H2,1H3] InChIKey [|WGYKZJWCGVVSQN]-[|UHFFFAOYAG] [|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] [|QECIGCMPORCORE]-[|UHFFFAOYAE] [|phenylacetic acid] [|InChI=1/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3] [|WLJVXDMOQOGPHL]-[|UHFFFAOYAR] [|n-butyl isocyanide] [| InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3] InChIKey: [|FSBLVBBRXSCOKU]-[|UHFFFAOYAR] [|Ugi Product] [|InChI=1/C3 ​1H34N2O2/c​1-3-5-19-3​2-31(35)30​(33(20-4-2​)29(34)21-​23-13-7-6-​ 8-14-23)28​-22-24-15-​9-10-16-25​(24)26-17-​11-12-18-2​7(26)28/h6​ -18,22,30H​,3-5,19-21​H2,1-2H3,(​H,32,35)] InChIKey: [|JNSYWEITXVHUPZ]-[|UHFFFAOYAJ]