Exp170

== =Objective= To synthesize a  [|Ugi adduct] from [|furfurylamine], [|phenanthrene-9-carboxaldehyde], [|phenyl acetic acid] and [|n-butyl isocyanide] in methanol using Ugi 4CR following Explan005. The target compound was ranked 29 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 furfurylamine, 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 || furfurylamine || 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) ||  || Density information: [|Ugi Chemicals]
 * ID/ Lib Rank || Solvent || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt Yes/No ||
 * 170/29 || Methanol || Phenanthrene-9-
 * Quantity || 1000uL || 0.5 mmol, 103.1 mg || 0.5mmol, 44.2uL

=Results=
 * **(170A)** || **(170B)** ||
 * [[image:Exp170A.JPG width="104" height="137" link="http://usefulchem.wikispaces.com/space/showimage/Exp170A.JPG"]] || [[image:Exp170B.JPG width="102" height="136" link="http://usefulchem.wikispaces.com/space/showimage/Exp170B.JPG"]] ||
 * **(170C)** ||  ||
 * [[image:Exp170C.JPG width="122" height="91" link="http://usefulchem.wikispaces.com/space/showimage/Exp170C.JPG"]] ||  ||

=Discussion= All results are recorded Master Table and Workflow Tables.

=Conclusion= A solid was formed but it was not washed - experiment aborted. Next time centrifugation and only vortexing should be used (no sonication), as described in EXPLAN005.

=Log=

2008-02-07
16:07- Charged a vial with 1 ml of methanol. 16:10- Started to weigh out the phenanthrene-9-carboxaldehyde 16:15- Started to weigh out the phenylacetic acid. 16:19- Added the furfurylamine to the vial and vortexed for 15 seconds. A clear solution was obtained. 16:21- Added the phenanthrene-9-carboxaldehyde to the vial and vortexed for 5 minutes. No clear solution was obtained. 16:28- Added the phenylacetic acid and vortexed for 3 minutes. A clear solution was obtained. 16:32- Added the n-butylisocyanide and vortexed for 15 seconds. A clear solution was obtained. 16:35- Took a photo of the vial (170A).

2008-02-08
15:15- Took another photo (170B) of the solid Ugi product in the vial. 16:14- Vortexed the product in the vial for 15 seconds. No solvent could be seen. //**this is where you should have centrifuged the first time**// 16:16- Added 500 ul of methanol to the vial and vortexed for 15 seconds. The solvent remained on top of the solid. 16:18- Sonicated the vial containing undissolved solid and methanol on top for 1 min, then vortexed it for 15 sec. At this time the solid packing at the bottom of the vial mixed well with the solvent and a pasty mixture covered the walls of the vial. 16:21- The vial was then emptied onto a clean watch glass. 16:22- Next 250 ul of methanol was added to the vial vortexed. Then the remaining solid was emptied onto the watch glass. 16:25- A photo was taken (170C) of the watch glass and empty vial. The methanol will evaporate so the product can be weighed.

=Tags=

[|furfurylamine] [|InChI=1/C5H7NO/c6-4-5-2-1-3-7-5/h1-3H,4,6H2] InChIKey: [|DDRPCXLAQZKBJP]-[|UHFFFAOYAX] [|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 Product] (//**not found in CS**//) [|InChI=1/C3 ​3H32N2O3/c​1-2-3-19-3​4-33(37)32​(30-22-25-​14-7-8-16-​27(25)28-1​ 7-9-10-18-​29(28)30)3​5(23-26-15​-11-20-38-​26)31(36)2​1-24-12-5-​ 4-6-13-24/​h4-18,20,2​2,32H,2-3,​19,21,23H2​,1H3,(H,34​,37)] InChIKey: [|RGGYLRDGJAJICY]-[|UHFFFAOYAH]