N-tert-butyl-5-(5-chloro-4-(5-(trans-2-methylcyclopropyl)-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide → 5-(5-chloro-4-(5-(trans-2-methylcyclopropyl)-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide
Reaction equation
C([NH:5][S:6]([C:9]1[S:10][C:11]([C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[C:24]([C@@H:26]4[CH2:28][C@H:27]4[CH3:29])[NH:23][N:22]=3)[C:17]([Cl:30])=[CH:16][N:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O>[Cl:30][C:17]1[C:18]([NH:20][C:21]2[CH:25]=[C:24]([C@@H:26]3[CH2:28][C@H:27]3[CH3:29])[NH:23][N:22]=2)=[N:19][C:14]([C:11]2[S:10][C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:13][CH:12]=2)=[N:15][CH:16]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
The solution of N-tert-butyl-5-(5-chloro-4-(5-(trans-2-methylcyclopropyl)-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide (90 mg, 0.19 mmol) in TFA (5 mL) was heated to reflux for 0.5 h. After concentration, the resulting residue was dilute with EtOAc and washed with water, saturate NaHCO3, brine, dried (Na2SO4) and filtered. The filtrate was concentrated to afford the title compound 5-(5-chloro-4-(5-(trans-2-methylcyclopropyl)-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide (Compound 320) (70 mg, 89%). LC-MS (m/z)=411 [M+H]% 1H NMR (400 MHz, DMSO-d6) δ 0.78-0.81 (m, 1H), 0.92-0.95 (m, 1H), 1.16 (m, 4H), 1.64-1.65 (m, 1H), 6.37 (s, 1H), 7.58 (d, J=4.0 Hz, 1H), 7.75 (d, J=3.6 Hz, 1H), 7.81 (s, 2H), 8.45 (s, 1H), 9.42 (s, 1H), 12.26 (s, 1H).