[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([NH:19][C:20]3[N:25]=[C:24]([CH2:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[CH:34]([CH3:38])[C:35]([NH2:37])=[O:36])[C:23]([C:39]([F:42])([F:41])[F:40])=[CH:22][N:21]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1.N1C=CC=CC=1>C(Cl)Cl>[C:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH:18]=[C:17]([NH:19][C:20]3[N:25]=[C:24]([CH2:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[CH:34]([CH3:38])[C:35]([NH2:37])=[O:36])[C:23]([C:39]([F:41])([F:40])[F:42])=[CH:22][N:21]=3)[CH:16]=[N:15]2)[CH2:12][CH2:13]1)(=[O:3])[CH3:2]Acetic anhydride (15 μL, 0.15 mmol) was added to a solution of 2-(2-(2-(2-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamide 56 (50 mg, 0.10 mmol) in DCM (5 mL) and pyridine (12 μL, 0.15 mmol) and the mixture was stirred at room temperature overnight. The volatiles were removed in vacuo and the resultant solid was suspended in water (25 mL) and sonicated for 5 minutes. The solid was collected by filtration and washed with sat. aq. Na2CO3 (20 mL), water (50 mL) then petroleum benzine 40-60° C. to give the title compound 58 as a white solid (42 mg, 77%). LCMS-D: rt 3.176 min; m/z 530.4 [M+H]+.
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