Exp163



=Objective= To synthesize a [|Ugi product] from phenanthrene-9-carboxaldehyde, furfurylamine, Mandelic acid, and t-butylisocyanide following the EXPLAN005. The compound will contribute towards a library for Falcipain2 inhibitors. This compunds was ranked 14 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

carboxaldehyde || furfurylamine || hydroxy(phenyl)acetic acid [Mandelic acid] racemic || tert-butylisocyanide || no || (density=0.735g/ml) ||  ||
 * ID/ Lib Rank || Solvent || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt Yes/No ||
 * 157/14 || Methanol || Phenanthrene-9-
 * Quantity || 1000uL || 0.5mmol, 103.1mg || .5mmol, 44.18 ul || 0.5mmol, 76.075 mg || 0.5mmol, 56.5uL

Density information found on the Ugi Chemicals[|Ugi Chemicals].

=Results=

all components (Exp163A)** || **One day after mixing all components (Exp163A1)** || all components (Exp163A2)** ||
 * **5 min after mixing
 * [[image:exp163A.jpg width="131" height="113" link="http://usefulchem.wikispaces.com/space/showimage/Exp163A.JPG"]] || [[image:Exp163A1.jpg width="151" height="112" link="http://usefulchem.wikispaces.com/space/showimage/Exp163A1.JPG"]] ||
 * **Two days after mixing

All results are recorded Master Table and Workflow Tables.

=Discussion= A clear yellow solution was obtained after all the reactants were added and vortexed as well as sonicated, what is interesting is that once the isocyanide was added to the solution it seemed to help with the overall solubility of the solution.

=Conclusion= No precipitate was observed after 24 hours.

=Log=

2008-01-24
15:22- Methanol added to one dram vial. 15:24- Furfurylamine was added to the vial and solution was vortexed for 20 seconds. 15:30-Weighed out Phenanthrene-9-carboxaldehyde. 15:32- Added Phenanthrene-9-carboxaldehyde to solution and vortexed for 20 seconds, a homogenous solution was not formed thus the solution was sonicated for 5 minutes, and still no homogeneous solution was formed. 15:38- Weighed out Mandelic acid. 15:40- Added Mandelic acid and vortexed for 20 seconds, no homogeneous solution was formed thus the solution was sonicated for 5 minutes. 15:46- Isocyanide was added to the solution and the vial was vortexed for 20 seconds and sonicated for 10 minutes. 15:56- A homogenous mixture was obtained. 16:00- A picture **163A** of the vial was taken. 15:16- Picture **163A1** was taken 24hrs after reaction. 14:02- Solution was vortexed for 15 seconds. 14:03 Picture **163A2** was taken. =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] [|Furfurylamine] [|InChI=1/C5H7NO/c6-4-5-2-1-3-7-5/h1-3H,4,6H2]InChIKey [|DDRPCXLAQZKBJP]-[|UHFFFAOYAX] [|tert-butyl isocyanide][|InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3] InChIKey [|FAGLEPBREOXSAC]-[|UHFFFAOYAL] [|Mandelic acid] [|InChI=1/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1] InChIKey [|IWYDHOAUDWTVEP]-[|UHFFFAOYAD] [|UgiProduct InChI=1/C33H32N2O4/c1-33(2,3)34-31(37)29(28-20-23-14-7-8-16-25(23)26-17-9-10-18-27(26)28)35(21-24-15-11-19-39-24)32(38)30(36)22-12-5-4-6-13-22/h4-20,29-30,36H,21H2,1-3H3,(H,34,37)] InChIKey [|KWDYVEIXHGZXHC]-[|UHFFFAOYAW]
 * 2008-01-25**
 * 2008-01-26**
 * 2008-03-13** 12:52 Obtained [|HNMR of Mandelic Acid]