exp168a.gif

Objective

To synthesize a Ugi product using Beta-methoxy-alpha-naphthaldehyde, Methylaminef, formic acid,and Tosylmethyl isocyanidefollowing the EXPLAN005 . The compound will contribute towards a library for Falcipain2 inhibitors.
This compunds was ranked 22 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

ID/ Lib Rank
Solvent
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
168-2/22
Methanol
B-methoxy-alpha-naphthaldehyde
methylamine, 2.0M solution in methanol.
formic acid
tosylmethyl isocyanide

Quantity
1000uL
0.5mmol, 93.105mg
0.5mmol, 19.78 ul (error)
0.5mmol, 18.86ul
0.5mmol, 97.62 mg


Density information found at the Ugi Chemicals page.

Results

5 min after mixing
all components

Exp168A.jpg

24 hours after mixing

Exp168B.jpg

All results are recorded Master Table and Workflow Tables .

Discussion

Conclusion

Experiment aborted because of a miscalculation of amine solution volume.

Log

2008-02-05

12:10 One dram vial charged with 1ml of methanol.
12:12 Amine in methanol solution was added to vial.
12:13 Vortexed for 15 seconds.
12:16 Added aldehyde to one dram vial.
12:17 Vortexed aldehyde for 5 minutes. Solution was obtained. It was not difficult to get a clear solution.
12:22 Added acid to vial. Even though the smallest pipette says 20ul it actually goes down to 10ul and up to 270ul. (how did you add 18.9 ul of formic acid? I thought our smallest micropipette had a min of 20 ul)
12:25 Vortexed for 15 seconds until solution was obtained.
12:26 Isocyanide was added to the vial, and vortexed for 5 mintues until solution was formed.
12:32 Picture was taken, but could not be uploaded onto the wiki due to a faulty connection with the camera.

2008-02-06

12:20 Picture was taken and no precipitate was formed.

Tags

Methylamine InChI=1/CH5N/c1-2/h2H2,1H3 InChIKey BAVYZALUXZFZLV-UHFFFAOYAN
Tosylmethyl isocyanide InChI=1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3 InChIKeyCFOAUYCPAUGDFF-UHFFFAOYAC
formic acid InChI=1/CH2O2/c2-1-3/h1H,(H,2,3) InChIKeyBDAGIHXWWSANSR-UHFFFAOYAT
Beta-methoxy-alpha-naphthaldehyde InChI=1/C12H10O2/c1-14-12-7-6-9-4-2-3-5-10(9)11(12)8-13/h2-8H,1H3 InChIKeyYIQGLTKAOHRZOL-UHFFFAOYAN
Ugi Product InChI=1/C2 ​3H24N2O5S/​c1-16-8-11​-18(12-9-1​6)31(28,29​)14-24-23(​27)22(25(2​ )15-26)21-​19-7-5-4-6​-17(19)10-​13-20(21)3​0-3/h4-13,​15,22H,14H​ 2,1-3H3,(H​,24,27) InChIKey RDBIZMTYKUDBFZ-UHFFFAOYAM