Reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[C:17]([C:18]([OH:20])=O)[C:11]=2[N:10]=1.[S:23]1[CH:27]=[CH:26][N:25]=[C:24]1[NH2:28].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[S:23]1[CH:27]=[CH:26][N:25]=[C:24]1[NH:28][C:18]([C:17]1[C:11]2[N:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:2]([F:1])([F:22])[F:21])[NH:13][C:12]=2[CH:14]=[CH:15][CH:16]=1)=[O:20]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid (3; 75 mg, 0.24 mmol) was taken up in DMF (2 mL) along with thiazol-2-amine (4; 24 mg, 0.24 mmol) and HATU (186 mg, 0.49 mmol). DIEA (81 μL, 0.49 mmol) was added. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with water and filtered. The collected solids were further purified by silica gel chromatography to afford the desired product, namely N-(thiazol-2-yl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide (Compound 208), as a white solid (35 mg, yield: 38%). MS (ESI) calcd for C18H11F3N4OS: 388.06; found: 389 [M+H].
Workup
- filtrationfiltered
- customThe collected solids were further purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-3c2ba477f6d94fa092f40a68852f9585
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846947B2
Linked notes
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