1-Hydroxybenzotriazole → HCID 57526693, compound

Participants

Reaction Steps

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 (R)-(−)-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: 1.75 min, m/z 637 (MH+); 1H NMR (400 MHz, CDCl) 8 1.31-1.44 (m, 3 H) 1.48-1.57 (m, 1 H) 1.58-1.69 (m, 2 H) 1.72-1.80 (m, 2 H) 1.87-1.96 (m, 3 H) 1.98-2.11 (m, 4 H)2.25-2.36 (m, 1 H) 2.42 (s, 3 H) 2.62-2.78 (m, 1 H) 2.78-2.89 (m, 1 H) 3.39 (ddd, J=12.53, 6.20 Hz, 1 H) 3.66 (s, 4 H) 3.74-3.85 (m, 2 H) 3.86-3.95 (m, 1 H) 4.40 (s, 1 H) 5.07 (s, 1 H) 6.60 (t, J=5.29 Hz, 1 H) 6.82 (s, 1 H) 7.34- 7.50 (m, 4 H) 7.52-7.59 (m, 1 H) 7.86 (d, J=8.56 Hz, 1 H) 7.97 (s, 1 H).

Provenance & Evidence