Acetyl chloride → HCID 59320892, compound

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:9]=[C:10]([C:14]3[CH:19]=[CH:18][N:17]4[C:20]([C:23]5[CH:24]=[C:25]([NH:29][C:30]([NH:32][CH2:33][C:34]([F:37])([F:36])[F:35])=[O:31])[CH:26]=[CH:27][CH:28]=5)=[CH:21][N:22]=[C:16]4[CH:15]=3)[CH:11]=[CH:12][CH:13]=2)[CH2:3][CH2:2]1.[C:38](Cl)(=[O:40])[CH3:39].CCN(CC)CC>CN(C=O)C>[C:38]([N:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:9]=[C:10]([C:14]3[CH:19]=[CH:18][N:17]4[C:20]([C:23]5[CH:24]=[C:25]([NH:29][C:30]([NH:32][CH2:33][C:34]([F:35])([F:36])[F:37])=[O:31])[CH:26]=[CH:27][CH:28]=5)=[CH:21][N:22]=[C:16]4[CH:15]=3)[CH:11]=[CH:12][CH:13]=2)[CH2:3][CH2:2]1)(=[O:40])[CH3:39]

Participants

Procedure

To a solution of 1-(3-{7-[3-(Piperidin-4-yloxy)-phenyl]-imidazo[1,2-a]pyridine-3-yl}-phenyl)-3-(2,2,2-trifluoro-ethyl)-urea (50 mg, 98 μmol in DMF(10 ml) was added acetyl chloride (6.3 μl, 82 μmol) and Et3N (14 μl). The reaction was stirred at room temperature for 3 h, then partitioned between EtOAc and H2O. The aqueous layer was again extracted with EtOAc, the organics combined, dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by preparative HPLC to give the title compound (17.5 mg).