Trifluoroacetic acid → 2-(acetylamino)-4-[2-(4-aminophenyl)ethyl]-N-methyl-1,3-thiazole-5-carboxamide
Reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:26]([NH:28][CH3:29])=[O:27])=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18]C(=O)OC(C)(C)C)=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O>>[C:1]([NH:4][C:5]1[S:6][C:7]([C:26]([NH:28][CH3:29])=[O:27])=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2]Participants
3
Procedure
tert-Butyl 4-(2-{2-(acetylamino)-5-[(methylamino)carbonyl]-1,3-thiazol-4-yl}ethyl)phenylcarbamate (95 mg) and trifluoroacetic acid (2 ml) were combined at 0° C. The reaction mixture was stirred at room temperature for an hour, and concentrated in vacuo. The residue was dissolved in chloroform. The organic solution was washed with 1N sodium hydroxide solution, water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative silica gel column chromatography with chloroform/methanol (10:1) as an eluent to give 2-(acetylamino)-4-[2-(4-aminophenyl)ethyl]-N-methyl-1,3-thiazole-5-carboxamide (49 mg) as an off-white amorphous substance.
Workup
- customwere combined at 0° C
- concentrationconcentrated in vacuo
- dissolutionThe residue was dissolved in chloroform
- washThe organic solution was washed with 1N sodium hydroxide solution, water and saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was purified by preparative silica gel column chromatography with chloroform/methanol (10:1) as an eluent
Sources & evidence
- ORD record
- ord-1ea56c4f357f4b7a8c031363e82ada96
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07442715B2
Reaction notes
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