3-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one → (R)-4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino [3,4-e]indazol-7-yl 4-(2-oxo-4,5-dihydro-1H-benzo[d][1,3]diazepin-3 (2H)-yl)piperidine-1-carboxylate

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Reaction Steps

(R)-4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino [3,4-e]indazol-7-yl 4-nitrophenyl carbonate (60 mg, 0.120 mmol) in dichloromethane (15 mL) was added 3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-one (32.5 mg, 0.132 mmol). The reaction mixture was stirred for 2 h. LC-MS analysis suggested formation of product (Rf=2.473, 605.22 (M+H)). The reaction mixture was washed with aqueous NaHCO3 followed by 1.0 M HCl. THe crude product was purified by flash chromatography using 5% MeOH in dichloromethane to give (R)-4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino [3,4-e]indazol-7-yl 4-(2-oxo-4,5-dihydro-1H-benzo[d][1,3]diazepin-3 (2H)-yl)piperidine-1-carboxylate (29.00 mg, 0.048 mmol, 40% yield). 1H NMR (500 MHz, CD3OD): in δ 8.30 (s, 1H), 7.32 (s, 1H), 7.09 (m, 3H), 6.93-6.87 (m, 3H), 6.09-6.05 (m, 1H), 5.50 (s, 2H), 5.44 (m, 1H), 4.68-4.54 (m, 1H), 4.39-4.35 (m, 2H), 4.32-4.19 (m, 1H), 4.16-4.05 (m, 3H), 3.55-3.50 (m, 3H), 3.12-2.92 (m, 2H), 1.87-1.74 (m, 4H); MS (ESI) 605 (M+H); Rf=2.47.

Provenance & Evidence