Exp167.gif

Objective

To synthesize a Ugi Product following the EXPLAN005 . The compound will contribute towards a library for Falcipain2 inhibitors, summary post. This compunds was ranked 12 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
138-2/12
Methanol
Phenanthrene-9-
carboxaldehyde
propylamine
3,4-methylenedioxyphenyl
acetic acid
n-butylisocyanide
aborted
Quantity
1000uL
0.5mmol, 103.1mg
0.5mmol, 41.1 ul
0.5mmol, 90.08 mg
0.5mmol, 52.28 uL
(density=0.795g/ml)


Density information found at the Ugi Chemicals page.

Results

30 min after mixing
all components
(167A)
Exp167.jpg





All results are recorded Master Table and Workflow Tables .

Discussion

Conclusion

Experiment aborted since no homogenous solution was formed. The aldehyde is not very soluble in the solvent, and no clear solution was ever obtained after the aldehyde was added. The insolubility of the aldehyde posed problems in other experiments as well but in others it didn't. This may be because of the reaction that the amine and aldehyde undergo to form a imine. The phenathrene may amine specific, in order to go into solution.

Log

2008-01-29

13:05 Added methanol to vial
13:10 Added propylamine to the vial and vortexed for 15 seconds.
13:15 Added aldehyde to vial and vortexed for 15 seconds followed by sonication for 5 minutes.
13:20- Vial was vortexed for 5 minutes, no solution obtained.
13:30 - The acid was added to the vial and vortexed for 15 seconds.
13:31- The vial was vortexed for 5 minutes.
13:36- The vial was sonicated for 5 minutes.
13:44- The isocyanide was added.
13:45 The solution was vortexed for 15 seconds.
13:46 The solution was sonicated for 5 minutes.
13:51 The solution was vortexed for an additional 10 minutes, no solution was obtained.
14:15 Picture 167A was taken.

Tags

propylamine InChI=1/C3H9N/c1-2-3-4/h2-4H2,1H3 InChIKey WGYKZJWCGVVSQN-UHFFFAOYAG
n-butylisocyanide InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3InChIKey FSBLVBBRXSCOKU-UHFFFAOYAR
Phenanthrene 9-carboxaldehyde InChI=1/C15H10O/c16-10-12-9-11-5-1-2-6-13%2811%2915-8-4-3-7-14%2812%2915/h1-10H InChIKey QECIGCMPORCORE-UHFFFAOYAE
3,4-methylenedioxyphenylacetic acid InChI=1/C9H8O4/c10-9(11)4-6-1-2-7-8(3-6)13-5-12-7/h1-3H,4-5H2,(H,10,11) InChIKeyODVLMCWNGKLROU-UHFFFAOYAB
UgiProduct InChI=1/C32H34N2O4/c1-3-5-16-33-32(36)31(27-20-23-10-6-7-11-24(23)25-12-8-9-13-26(25)27)34(17-4-2)30(35)19-22-14-15-28-29(18-22)38-21-37-28/h6-15,18,20,31H,3-5,16-17,19,21H2,1-2H3,(H,33,36) InChIKey XZPSENWJJNOGKV-UHFFFAOYAP