反应详情

A solution of 13-cyclohexyl-6-[[4-(4-morpholinyl)-1-piperidinyl]carbonyl]-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid (40 mg, 0.07 mmol), N,N-diisopropylethylamine (60 μL, 0.34 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (19 mg, 0.1 mmol), 1-hydroxybenzotriazole (14 mg, 0.1 mmol), and furfuryl amine (10 mg, 0.1 mmol) in CH2Cl2 (1.5 mL) was stirred at r.t. overnight, diluted with CH2Cl2 (3 mL), and chromatographed on silica gel (gradient elution: 0%→10% MeOH in CH2Cl2) to afford a yellow oil. Et2O (5 mL) was added to dissolve the oil, and concentration afforded the title compound as a pale yellow solid (42 mg, 95% yield). LC/MS (ESI) retention time: 1.74 min, m/z 633 (MH+); 1H NMR (400 MHz, CDCl3 ) δ 1.29-1.44 (m, 3 H) 1.46-1.57 (m, 1 H) 1.69-1.81 (m,3 H) 1.86-1.97 (m, 1 H) 1.98-2.11 (m, 3 H) 2.27-2.37 (m, 1 H) 2.38-2.49 (m, 4 H) 2.61-2.78 (m, 2 H) 2.78-2.89 (m, 1 H) 3.66 (s, 4 H) 4.38 (s, 1 H) 4.66 (d, J=5.29 Hz, 2 H) 5.06 (s, 1 H) 6.22-6.41 (m, 2 H) 6.64 (t, J=5.04 Hz, 1 H) 6.81 (s, 1 H) 7.33-7.50 (m, 5 H) 7.51-7.61 (m, 1 H) 7.85 (d, J=8.31 Hz, 1 H) 7.97 (s, 1 H); 13C NMR (101 MHz, CDCl3) δ 26.20, 27.02, 33.27, 36.73, 37.04, 41.92, 49.45, 61.67, 66.94, 107.54, 108.90, 110.48, 116.84, 120.05, 121.19, 127.05, 127.95, 128.21, 129.24, 130.08, 130.96, 131.24, 133.24, 134.00, 135.18, 136.39, 142.15, 151.57, 167.74, 168.88.

1. customchromatographed on silica gel (gradient elution: 0%→10% MeOH in CH2Cl2)
2. customto afford a yellow oil
3. dissolutionto dissolve
4. concentrationthe oil, and concentration