Exp186

=Objective= To synthesize a Ugi Product following the EXPLAN005 with [|benzaldehyde], aniline, 1-pyrenebutyric acid and n-butylisocyanide. The compound will contribute towards a library for Falcipain2 inhibitors. This compounds was ranked 83 in the [|DEXP014-V2B]   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]. The purpose of this experiment is to determine whether this set of starting material is soluble in different solvents. It was determined in Exp181-83 that they are insoluble in methanol.

=Procedure= As described in Explan005 This reaction used [|benzaldehyde], [|aniline], [|n-butylisocyanide] and [|1-pyrenebutyric acid].

This experiment is Ranked 83. It is a repeat of Exp 181-83 in three different solvents: ethanol, acetonitrile, and dichloromethane. Exp186-1 is in ethanol, Exp186-2 is in acetonitrile, and Exp186-3 is in dichloromethane.

Insoluble || Insoluble || Insoluble ||
 * ID/ Lib Rank || Solvent || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt Yes/No ||
 * 186-1/83 || ethanol || Benzaldehyde || Aniline || 1-Pyrenebutyric acid || n-butylisocyanide || Reagents
 * 186-2/83 || acetonitrile || Benzaldehyde || Aniline || 1-Pyrenebutyric acid || n-butylisocyanide || Reagents
 * 186-3/83 || dichloromethane || Benzaldehyde || Aniline || 1-Pyrenebutyric acid || n-butylisocyanide || Reagents
 * Quantity || 1000uL || (0.5mmol-50.8uL) || (0.5mmol-45.5uL) || (0.5mmol-144.1mg) || (0.5mmol-53uL) ||  ||

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

=Results= Photos taken directly after all the components were charged and vortexed.
 * **186-1 A** || **186-2 A** || **186-3 A** ||
 * [[image:Exp186-1.JPG width="117" height="89" link="http://usefulchem.wikispaces.com/space/showimage/Exp186-1.JPG"]] || [[image:Exp186-2.JPG width="115" height="87" link="http://usefulchem.wikispaces.com/space/showimage/Exp186-2.JPG"]] || [[image:Exp186-3.JPG width="120" height="90" link="http://usefulchem.wikispaces.com/space/showimage/Exp186-3.JPG"]] ||

=Discussion=

=Conclusion= The starting materials are insoluble in each solvent.

=Log=

2008-05-07
16:32- Charged vial 186-1 with 1000 ul of ethanol. 16:36- Charged vial 186-2 with 1000 ul of acetonitrile. 16:40- Charged vial 186-3 with 1000 ul of dichloromethane. 16:44- Weighed out the 1-pyrenebutyric acid for each of the three samples. 16:56- Added the aniline to the vials. 16:59- Vortexed each vial 15 seconds each. Each sample was clear. 17:02- Added the benzaldehyde to each vial. 17:04- Vortexed vials for 2 minutes each. Each sample was clear. 17:12- Added the 1-pyrenebutyric acid to each vial. 17:15- Vortexed each vial 3 min. No clear solution was obtained. 17:25- Added the n-butyl isocyanide to each vial. 17:28- Vortexed 2 minutes each. No clear solutions were obtained. 17:35- Photos were taken of the vials **186-1 A**, **186-2 A**, and **186-3 A**.

=Tags=

[|benzaldehyde] InChI: [|InChI=1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H] InChIKey: [|HUMNYLRZRPPJDN]-[|UHFFFAOYAE] [|aniline] InChI: [|InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2] InChIKey: [|PAYRUJLWNCNPSJ]-[|UHFFFAOYAP] [|1-pyrenebutyric acid] [|InChI=1/C20H16O2/c21-18(22)6-2-3-13-7-8-16-10-9-14-4-1-5-15-11-12​-17(13)20(16)19(14)15/h1,4-5,7-12H,2-3,6H2,(H,21,22)] InChIKey: [|QXYRRCOJHNZVDJ]-[|UHFFFAOYAV] [|n-butylisocyanide] InChI: [|InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3] InChIKey: [|FSBLVBBRXSCOKU]-[|UHFFFAOYAR]