Exp179

== =Objective= To synthesize a [|Ugi Product] following the EXPLAN005. The compound will contribute towards a library for Falcipain2 inhibitors. This compounds was ranked 44 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], [|Aniline], [|4-chlorophenyl acetic acid] and [|t-butyl isocyanide] [|HNMR] carboxaldehyde || aniline || 4-chlorophenyl acetic acid || t-butylisocyanide || N/A || (density=0.719g/ml) || 0.5mmol, 85.3mg || 0.5mmol, 56.3uL (density=0.795g/ml) ||  ||
 * Phenanthrene-9-Carboxaldehyde** (solid from Sigma-Aldrich)
 * ID/ Lib Rank || Solvent || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt Yes/No ||
 * 179/44 || Methanol || Phenanthrene-9-
 * Quantity || 1500uL || 0.5mmol, 103.1mg || 0.5mmol, 45.6uL

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

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

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

=Discussion= This experiment is another example of the apparent amine-dependent solubility of the phenanthrene carboxaldehyde. One might hypothesize that the aromaticity of the aniline increases its stability and thus decreases its willingness to dissolve the phenanthrene-9-carboxaldehyde.

=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=

2008-03-03
16:00- Charged a vial with 1000 ul of methanol. 16:02- Weighed out the Phenanthrene-9-carboxaldehyde. 16:07- Weighed out the phenylacetic acid. 16:15- Added the aniline to the vial. 16:16 Vortexed vial 1 min 16:21- Added the phenanthrene-9-carboxaldehyde. 16:22-Vortexed vial 2 min 16:24- Added the 4-chlorophenyl acetic acid. 16:25-Vortexed vial 1 min, did not dissolve, moved on to next addition 16:26- Added the t-butyl isocyanide. 16:27-Vortexed 5 min, still no dissolution, made decision to add methanol to dilute it. 16:33-Added extra 500ul of methanol 16:34-Vortexed 5 min, still no dissolution 16:40-Concluded that no further dissolution possible. 16:45- A photo was taken (179A) to demonstrate insolubility.

=Tags= [|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] InChIKey: [|QECIGCMPORCORE]-[|UHFFFAOYAE] [|Aniline] [|InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2] InChIKey: [|PAYRUJLWNCNPSJ]-[|UHFFFAOYAP] [|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)] InChIKey: [|CDPKJZJVTHSESZ]-[|UHFFFAOYAC] [|t-butyl isocyanide][|InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3]InChIKey: [|FAGLEPBREOXSAC]-[|UHFFFAOYAL] [|Ugi Product] [|InChI=1/C3 ​4H31ClN2O2​/c1-34(2,3​)36-33(39)​32(30-22-2​4-11-7-8-1​4-27(24)28​ -15-9-10-1​6-29(28)30​)37(26-12-​5-4-6-13-2​6)31(38)21​-23-17-19-​ 25(35)20-1​8-23/h4-20​,22,32H,21​H2,1-3H3,(​H,36,39)] InChIKey: [|KKLAGOLUKOTRAL]-[|UHFFFAOYAS]