Triethylamine → Carbamic acid, N-[trans-4-[[(3-chlorobenzo[b]thien-2-yl)carbonyl][[3-(4-pyridinyl)phenyl]methyl]amino]cyclohexyl]-, 1,1-dimethylethyl ester

Participants

Reaction Steps

To a solution of 18 (410 mg, 1.1 mmol) and Et3N (280 μL, 2.0 mmol) in CH2Cl2 (10 mL) was added 3-chlorobenzo[b]thiophene-2-carbonyl chloride 12 (278 mg, 1.2 mmol), and the reaction mixture was stirred at room temperature for 0.5 h. The solvent was removed and the residue was purified by a flash chromatography on silica gel (acetone/PE=5:1) to give the desired product 19 (587 mg) in 96% yield; 1H-NMR (400 MHz, CDCl3): 8.65 (br, 2H), 7.20-8.20 (m, 10H), 3.70-5.00 (m, 4H), 3.20-3.40 (br, 1H), 1.75-2.20 (m, 4H), 1.42-1.75 (br, 2H), 1.38 (s, 9H), 0.90-1.30 (br, 2H); 13C NMR (100 MHz, CDCl3): 163.7, 155.1, 150.2, 148.1, 147.7, 139.2, 138.4, 137.2, 135.6, 130.0, 129.3, 127.6, 126.5, 126.2, 125.5, 122.7, 122.5, 121.6, 119.0, 79.2, 58.7, 48.5, 45.1, 32.1, 30.5, 29.7, 29.3, 28.3; HRMS (EI) calcd for C32H34ClN3O3S (M+) 575.2009; found 575.2018.

Provenance & Evidence