Exp160

= = = = =Objective= To synthesize a [|Ugi adduct] from [|furfurylamine], [|phenanthrene-9-carboxaldehyde], [|3,4-dihydroxyphenyl acetic acid] and [|n-butyl isocyanide] in methanol using Ugi 4CR following Explan005. The target compound was ranked 19 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, 3,4-dihydroxyphenyl 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 || 3,4-dihydroxyphenyl acetic acid || n-butyl isocyanide || No || (density=1.099g/ml) || 0.5mmol, 84.08 mg || 0.5mmol, 52.28 ul (density=0.795g/ml) ||  ||
 * ID/ Lib Rank || Solvent || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt Yes/No ||
 * 160/19 || Methanol || Phenanthrene-9-
 * Quantity || 1000uL || 0.5 mmol, 103.12 mg || 0.5mmol, 44.19uL

Density information: [|Ugi Chemicals]

=Results=

all components (160A)** || **One day after mixing all components (160B)** ||
 * **5 min after mixing
 * [[image:Exp160day1.JPG width="141" height="105" link="http://usefulchem.wikispaces.com/space/showimage/Exp160day1.JPG"]] || [[image:Exp160day2.JPG width="143" height="107" link="http://usefulchem.wikispaces.com/space/showimage/Exp160day2.JPG"]] ||


 * **After sonication (160C)** ||  ||
 * [[image:Exp160day2a.JPG width="133" height="99" link="http://usefulchem.wikispaces.com/space/showimage/Exp160day2a.JPG"]] ||  ||

=Discussion=

The phenanthrene-9-carboxaldehyde appeared to be less soluble than the other starting materials. The vortex time recorded in the log is five minutes compared to the 15 seconds necessary for the other components. All results are recorded Master Table and Workflow Tables.

=Conclusion=

After the vial set out at room temperature for a day and was sonicated. No precipitate was formed.

=Log= 17:13- Started to weigh out the phenanthrene-9-carboxaldehyde. 17:20- Started to weigh out the 3,4-dihydroxyphenyl acetic acid. 17:25- Charged a vial with 1 mL of methanol. 17:28- Added the furfurylamine to the vial and vortexed for 15 seconds. A clear solution was obtained. 17:33- Added the phenanthrene-9-carboxaldehyde to the vial and vortexed for 5 minutes until a clear solution was obtained. 17:38- Added the 3,4-dihydroxyphenyl acetic acid to the vial and vortexed for 15 seconds. A clear solution was obtained. 17:44- Added the n-butyl isocyanide to the vial and vortexed for 15 seconds. A clear solution was obtained. 17:49- Took a photo **(160A)** of the vial, and left it to sit for 24 hours at room temperature.
 * 2008-01-18**

16:50- Took a photo **(160B)** of the vial. There was no precipitate that formed. 16:55- Put the vial into the sonicator for ten minutes. 17:05- Removed the vial and took another picture **(160C)**. No solid has formed.
 * 2008-01-19**

=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] [|3,4-dihydroxyphenyl acetic acid] [|InChI=1/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)] InChIKey: [|CFFZDZCDUFSOFZ]-[|UHFFFAOYAU] [|n-butyl isocyanide] [|InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3] InChIKey: [|FSBLVBBRXSCOKU]-[|UHFFFAOYAR] [| Ugi product] InChIKey: [|NVRQEIRPSKDYGZ]-[|UHFFFAOYAO]