Objective

To synthesize a Ugi Product following the EXPLAN005 with benzaldehyde, aniline, 1-pyrenebutyric acid and n-butylisocyanide. The compound will contribute towards a library for Falcipain2 inhibitors.
This compounds was ranked 83 in the DEXP014-V2B 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. The purpose of this experiment is to determine whether this set of starting material is soluble in different solvents. It was determined in Exp181-83 that they are insoluble in methanol.

Procedure

As described in Explan005
This reaction used benzaldehyde, aniline, n-butylisocyanide and 1-pyrenebutyric acid .

This experiment is Ranked 83. It is a repeat of Exp 181-83 in three different solvents: ethanol, acetonitrile, and dichloromethane.
Exp186-1 is in ethanol, Exp186-2 is in acetonitrile, and Exp186-3 is in dichloromethane.

ID/ Lib Rank
Solvent
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
186-1/83
ethanol
Benzaldehyde
Aniline
1-Pyrenebutyric acid
n-butylisocyanide
Reagents
Insoluble
186-2/83
acetonitrile
Benzaldehyde
Aniline
1-Pyrenebutyric acid
n-butylisocyanide
Reagents
Insoluble
186-3/83
dichloromethane
Benzaldehyde
Aniline
1-Pyrenebutyric acid
n-butylisocyanide
Reagents
Insoluble
Quantity
1000uL
(0.5mmol-50.8uL)
(0.5mmol-45.5uL)
(0.5mmol-144.1mg)
(0.5mmol-53uL)


Density information found on the Ugi Chemicals Page in Left Navigation Bar.

Results

Photos taken directly after all the components were charged and vortexed.
186-1 A
186-2 A
186-3 A
Exp186-1.JPG
Exp186-2.JPG
Exp186-3.JPG


Discussion



Conclusion

The starting materials are insoluble in each solvent.

Log

2008-05-07

16:32- Charged vial 186-1 with 1000 ul of ethanol.
16:36- Charged vial 186-2 with 1000 ul of acetonitrile.
16:40- Charged vial 186-3 with 1000 ul of dichloromethane.
16:44- Weighed out the 1-pyrenebutyric acid for each of the three samples.
16:56- Added the aniline to the vials.
16:59- Vortexed each vial 15 seconds each. Each sample was clear.
17:02- Added the benzaldehyde to each vial.
17:04- Vortexed vials for 2 minutes each. Each sample was clear.
17:12- Added the 1-pyrenebutyric acid to each vial.
17:15- Vortexed each vial 3 min. No clear solution was obtained.
17:25- Added the n-butyl isocyanide to each vial.
17:28- Vortexed 2 minutes each. No clear solutions were obtained.
17:35- Photos were taken of the vials 186-1 A, 186-2 A, and 186-3 A.


Tags


benzaldehyde InChI: InChI=1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H InChIKey: HUMNYLRZRPPJDN-UHFFFAOYAE
aniline InChI: InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2 InChIKey: PAYRUJLWNCNPSJ-UHFFFAOYAP
1-pyrenebutyric acid InChI=1/C20H16O2/c21-18(22)6-2-3-13-7-8-16-10-9-14-4-1-5-15-11-12‚Äč-17(13)20(16)19(14)15/h1,4-5,7-12H,2-3,6H2,(H,21,22) InChIKey: QXYRRCOJHNZVDJ-UHFFFAOYAV
n-butylisocyanide InChI: InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3 InChIKey: FSBLVBBRXSCOKU-UHFFFAOYAR