1-Hydroxybenzotriazole → HCID 57526693, compound

Participants

Reaction Steps

13-cyclohexyl-6-[[4-(4-morpholinyl)-1-piperidinyl]carbonyl]-N-[[(2S)-tetrahydro-2-furanyl]methyl-7H-indolo[2,1-a[2]benzazepine-10-carboxamide. 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 (S)-(+)-tetrahydrofurfurylamine (10 mg, 0.1 mmol) in CH2Cl2 (1.5 mL) was stirred at r.t. overnight, diluted with CH2Cl2 (5 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 an off-white solid (32 mg, 72% yield). LC/MS (ESI) retention time: 1.73 min, m/z 637 (MH+); 1H NMR (400 MHz, CDCl3) δ 1.27-1.43 (m, 3 H) 1.47-1.57 (m, 1 H) 1.58-1.70 (m, 2 H) 1.70-1.81 (m, 2 H) 1.86-1.97 (m, 3 H) 1.98-2.12 (m, 4 H) 2.25-2.35 (m, 1 H) 2.42 (s, 3 H) 2.63-2.77 (m, 1 H) 2.78-2.89 (m, 1 H) 3.29-3.46 (m, 1 H) 3.65 (s, 4 H) 3.74-3.85 (m, 2 H) 3.85-3.98 (m, 1 H) 4.09 (ddd, J=14.16, 7.11, 3.40 Hz, 1 H) 4.39 (s, 1 H) 5.08 (s, 1 H) 6.67-6.75 (m, 1 H) 6.82 (s, 1 H) 7.34-7.39 (m, 1 H) 7.40-7.50 (m, 3 H) 7.52-7.59 (m, 1 H) 7.86 (d, J=8.56 Hz, 1 H) 7.99 (s, 1 H).

Provenance & Evidence