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UC on ChemSpider
Alicia's Masters Thesis
Open Web Drug Dev.
To Do List
Ugi NMR Analysis
Synthesize seven Ugi products six of which were synthesized previously. THF is used as solvent for compounds containing polyaromatics. Target Ugi product 215-G is ranked 2 in the
Suicide Inhibitor Library-1 according to Goldscore
Equimolar amounts of aldehyde, amine, carboxylic acid and an isocyanide was dissolved in THF in glass vials and vortexed to dissolve them. Addition of the components to THF followed the sequence aldehyde, amine, carboxylic acid and isocyanide. After component was added the vials was vortexed to obtain homogenous solution. Vials were left undisturbed for four days, a picture was obtained each day to check if a solid precipitate had formed in them. The solid precipiate (if formed) was then washed with hot methanol (2-3mL) and the residue collected after filteration was dried in a disiccator. The product was analyzed by HNMR.
Characterization of UCExp215F-2
:2-[benzyl-[2-(4-chlorophenyl)acetyl]amino]-N-butyl-2-(9-phenanthryl)acetamide;C35H33ClN2O2; 1H NMR (
ppm, CDCl3) 0.88 (t, 3H J 7.3Hz),1.24-1.32 (m, 2H), 1.4-1.5 (m, 2H), 3.2-3.32 (m, 1H), 3.36-3.47(m, 1H), 3.52-3.72 (m, 2H), 4.66-4.82 (m, 2H), 5.82 (t, 1H J 5.6Hz), 6.6-6.68 (m, 2H), 6.72-6.9 (m, 3H), 7.07 (d, 2H J 8.3Hz), 7.11 (s, 1H), 7.23 (d, 2H, J 8.3Hz), 7.52-7.59 (m, 1H), 7.6-7.71 (m, 3H), 7.78 (d, 1H J 7.3Hz), 7.87 (s, 1H), 8.09 (d, 1H, J 7.8Hz), 8.57 (d, 1H, J 8.3Hz), 8.63 (d, 1H, J 7.8Hz) yield 30.2%
Labile Proton test
Only one Ugi product (UC215-F2) could be isolated from this experiment.
20:00 To 2mL solutions of phenanthrene-9-carboxaldehyde (2mmol, 412.48mg ) in THF labeled
2mmol of remaining three components components from the
were added. All the components dissolved freely in each solution. Similarly to
, a 2mL THF solution of 2-naphthlaldehyde (2mmol, 312.36mg), 2mmols of the remaining components were added. All the components again freely dissolved in the solution. Addition of the components followed the order, aldehyde (1st dissolved in the solvent), amine (2nd), acid (3rd) and finally isocyanide (4th). After the addition of each component the solutions were vortexed for 30s (each time)
21:00 Solutions labeled
were prepared in 1mL THF. Initially, the aldehyde was dissolved in the solvent, followed by the additon of amine, acid and the isocyanide in that order. The individual amount of each component added to the solution is listed in the
22:00 A solution of
was prepared in methanol...first 1mmol of 5-bromothiophenecarboxaldehyde (1mmol) was dissolved in methanol (1mL). To this 3-chloroaniline (1mmol) was added..the solution remained clear...soon after the addition of chloroacetic acid (1mmol) the entire solution turned in to a yellow/ brown precipitate (within 3min). To dissolve this precipitate methanol (1mL) was further added to it..this did not dissolve the ppt. This is when THF (1mL) was added to the reaction vial. and vortexed for 30s. The entire ppt dissolved completely in solution. After each addition the solutions were vortexed for 30s (each time)
23:00 The reaction vials were left in the hood at room temperature.
: A 2M methanolic solution of methylamine was used in reactions 215-C, 215D and 215E as the amine component.
12;00 Except solution 215-G all the solutions still remain clear. Vial labeled 215-G appears to have accumulated some brown colored ppt at the bottom.
17:30 Obtained a picture of the solutions.
21:03 Obtained a picture of the solution- None of the solutions have developed any solid in them. All the solutions were clear.
21:30 To the vial labeled 215-A, n-hexane (3mL) was added drop wise...still nothing.
21:45 The vials were left in a freezer..
15:36 Removed the vials from the freezer. Vials 215-E and 215F have developed solids in them. Obtained a picture of the vials. Left the vials back in the freezer.
14:00 The vials were removed from the freezer, no change in conditions of the solutions, 215E and 215F had accumulated ppts.
14:30 Poured out the reaction mixtures from the vials on to clean watch glass (labeled with the solution numbers) and left them in the hood uncovered for the solvent to evaporate.
18:00 Except for 215A and 215B which remained as oily liquids, rest of the solutions had some kind of solid accumulation after evaporation on the watch glass..(could be the starting materials). To the residue from 215-C to 215G methanol was added and the solid was scraped out into small beakers...additional methanol was added to the beakers (approximately 2ml)
19:00 Set the beakers on a hot water bath and tried to dissolve the solid in it...none of the solid (from the reaction mixtures) dissolved in hot methanol except 215G, which was then filtered and set aside to cool..this is 215G-.After cooling down all the reaction mixtures (except 215F) was parafilmed and set in a hood)...
19:30 The solid in 215F which did not dissolve in hot methanol was filtered and washed further with 2-3ml methanol. The residue collected after filtration was set to dry in a desiccator.
12:00 Removed 215F from the desiccator and obtained
(332mg- yied- 30.2%). Obtained an HNMR of a small sample in CDCl3, also permformed a labile proton test by adding D2O (200uL) to the NMR tube contained a small amount of 215F-2 in CDCl3 (700uL)...the NMR tube was shaken vigourously for 2min inorder to felicitate exchange of labile protons with deuteriums.
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