反应详情

BCl3 (1 M in CH2Cl2, 3.28 mL, 3.28 mmol, 4.0 equiv.) was added to a stirred solution of (Z)—N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(prop-1-enyl)pyrimidin-2-yl)thiophene-2-sulfonamide (375.6 mg, 0.82 mmol, 1.0 equiv.) in CH2Cl2 (20 mL) at room temperature under nitrogen. The reaction mixture was stirred for 30 min and then quenched with aq. NaHCO3 in ice bath. The reaction mixture was extracted with ethyl acetate and washed with water, brine, dried and evaporated. The crude product was crystallized with THF/isopropyl to afford (Z)-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-(prop-1-enyl)pyrimidin-2-yl)thiophene-2-sulfonamide (Compound 207) (255.1 mg, 77.4%). LC-MS (m/z)=403 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.75-0.76 (m, 2H), 0.95-1.00 (m, 2H), 1.79-1.81 (m, 2H), 1.90 (d, J=6.0 Hz, 1H), 1.93-1.97 (m, 1H), 5.60-6.04 (m, 0.6H), 6.26-6.31 (m, 0.4H), 6.46-6.49 (s, 1.5H), 6.79 (d, J=15.2 Hz, 0.4H), 7.57-7.59 (m, 1H), 7.74-7.79 (m, 3H), 8.19 (s, 0.6H), 8.39 (s, 0.4H), 8.94 (s, 0.5H), 9.33 (s, 0.3H).

1. customquenched with aq. NaHCO3 in ice bath
2. extractionThe reaction mixture was extracted with ethyl acetate
3. washwashed with water, brine
4. customdried
5. customevaporated
6. customThe crude product was crystallized with THF/isopropyl