反应详情

To a solution of tert-butyl 6-(2-anilino-2-oxoethyl)-9,10-dichloro-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (40 mg, 0.082 mmol) in CH2Cl2 (3 mL), TFA (0.032 mL, 0.41 mmol) was added while stirring at rt. Additional TFA (0.032 mL, 0.41 mmol) was added after 3 h. After 69 h, TFA (0.25 mL, 3.2 mmol) was added along with additional CH2Cl2 (3 mL). The reaction was quenched with 10% aqueous NaOH (5 mL) after 70 h and extracted with CH2Cl2 (3×15 mL). The combined organic layers were washed with brine, dried over Na2SO4, decanted, and concentrated to give 30 mg of crude solid. The hydrochloride salt prepared to give 23 mg (67%) of a white solid: mp 274.0-276.0° C.; 1H NMR (300 MHz, DMSO) δ 7.58 (d, J=7.9 Hz, 2H), 7.52 (d, J=8.7 Hz, 1H), 7.32 (m, 3H), 7.07 (t, J=7.2 Hz, 1H), 5.14 (s, 2H), 3.56 (m, 2H), 3.18 (m, 2H); IR (diffuse reflectance) 2995, 2983, 2967, 2948, 2940, 2936, 2809, 2767, 1680, 1600, 1549, 1448, 1314, 797, 759 cm−1; MS (ES+) m/z 388 (M+H+), 361, 359, 268, 266, 242, 241, 240, 238, 228, 226; Anal. Calcd for C20H19Cl2N3O.HCl: C, 56.55; H, 4.75; N, 9.89; found: C, 56.25; H, 4.89; N, 9.50.

1. customThe reaction was quenched with 10% aqueous NaOH (5 mL) after 70 h
2. extractionextracted with CH2Cl2 (3×15 mL)
3. washThe combined organic layers were washed with brine
4. dry with materialdried over Na2SO4
5. customdecanted
6. concentrationconcentrated
7. customto give 30 mg of crude solid