Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH:7]1([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:33][CH2:32][CH:31](NC)[CH2:30]4)=[CH:25][CH:24]=3)=[O:21])=[CH:15][CH:14]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1.C[CH2:37][N:38](C(C)C)C(C)C>ClCCl>[CH:7]1([O:12][C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:20](=[O:21])[NH:22][C:23]3[CH:28]=[CH:27][C:26]([N:29]4[CH2:33][CH2:32][CH:31]([CH2:37][NH:38][C:2](=[O:3])[O:4][CH2:5][CH3:6])[CH2:30]4)=[CH:25][CH:24]=3)=[CH:17][CH:18]=2)[CH2:8][CH2:9][CH2:10][CH2:11]1Ethyl chloroformate (8 μl) was added dropwise to a solution of 1-(4-cyclopentyloxyphenyl)-3-[4-(3-methylaminopyrrolidin-1-yl)phenyl]urea (20 mg) and Hünig's base (10 mg) in dichloromethane (3 ml). After 12 hours, the reaction mixture was concentrated and the residue was purified by preparative HPLC. This resulted in the product with the molecular weight of 466.59 (C26H34N4O4); MS (ESI): 467 (M+H+) as hydrotrifluoroacetate.
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