Exp164

== = = =Objective= To synthesize a [|Ugi adduct] from aniline, phenanthrene-9-carboxaldehyde, phenyl acetic acid and n-butyl isocyanide in methanol using Ugi 4CR following Explan005. The target compound was ranked 20 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= To a one dram vial, charged with methanol (1mL) and aniline, phenanthrene-9-carboxaldehyde, phenyl acetic acid and n-butyl isocyanide (0.5mmol each) was added in that order. After each addition, the resulting solution was vortexed for at least 15 seconds and confirmed that a homogeneous solution had been obtained. The vial was capped tight and left at room temperature for 1 day.

carboxaldehyde || aniline || phenyl acetic acid || n-butyl isocyanide || Aborted || (density=1.022g/ml) || 0.5mmol, 68.08 mg || 0.5mmol, 52.28 ul (density=0.795g/ml) ||  ||
 * ID/ Lib Rank || Solvent || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt Yes/No ||
 * 164/20 || Methanol || Phenanthrene-9-
 * Quantity || 1500uL || 0.5 mmol, 103.12 mg || 0.5mmol, 45.6uL

Density information found on the Sigma-Aldrich website (www.sigmaaldrich.com)

=Results=

all components (164A)** ||  ||
 * **5 min after mixing
 * [[image:Exp164A.JPG width="147" height="110" link="http://usefulchem.wikispaces.com/space/showimage/Exp164A.JPG"]] ||  ||

=Discussion=

All results are recorded Master Table and Workflow Tables.

=Conclusion= This Ugi reaction failed to dissolve, possibly due to the apparent selective solubility of phenanthrene-9-carboxaldehyde as discussed here.

=Log=

2008-01-24
15:37- Charged a vial with 1 ml of methanol. 15:39- Started to weigh out the phenanthrene-9-carboxaldehyde 15:45- Started to weigh out the phenylacetic acid. 15:49- Added the aniline to the vial and vortexed for 15 seconds. A clear solution was obtained. 15:52- Added the phenanthrene-9-carboxaldehyde to the vial and vortexed for 6 minutes. No clear solution was obtained. 15:59- Added the phenylacetic acid and vortexed for 5 minutes. No clear solution was obtained. 16:08- Added the n-butylisocyanide and vortexed for 5 minutes. No clear solution was obtained. 16:15- Added another 0.5 ml of methanol to the vial and vortexed for one minute. There was no change in the vial and no clear solution. 16:17- Vortexed for 5 more minutes. No clear solution was obtained. 16:25- Took a photo of the vial. This experiment needs to be aborted, because the components did not all go into solution.

=Tags= [|aniline] [|InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2] InChIKey: [|PAYRUJLWNCNPSJ]-[|UHFFFAOYAP] [|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] [|phenyl acetic acid] [|InChI=1/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)] InChIKey: [|WLJVXDMOQOGPHL]-[|UHFFFAOYAR] [|n-butyl isocyanide] [|InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3][|InChIKey:][|FSBLVBBRXSCOKU]-[|UHFFFAOYAR] [|Ugi adduct] [|InChI=1/C3 ​4H32N2O2/c​1-2-3-22-3​5-34(38)33​(31-24-26-​16-10-11-1​9-28(26)29​ -20-12-13-​21-30(29)3​1)36(27-17​-8-5-9-18-​27)32(37)2​3-25-14-6-​ 4-7-15-25/​h4-21,24,3​3H,2-3,22-​23H2,1H3,(​H,35,38)] InChIKey: [|UBRMSVUGUNBCHK]-[|UHFFFAOYAX]