Dichloromethane → HCID 68568015, compound

Participants

Reaction Steps

Amine 14 (62 mg) and NEt3 (0.1 mL) were stirred in THF (6 mL) and DCM (6 mL) and cooled to 5° C. 4-Cyanophenylsulfonyl chloride (30 mg) was added dropwise by syringe, and stirring was continued at rt for 2 h, then the reaction mixture was concentrated. The residue was redissolved in DCM and washed with saturated NaHCO3, brine, and dried over MgSO4. After removal of solvent, the crude product was purified by preparative TLC (silica gel, DCM/MeOH=12/1) to give 16 mg (36%) of 15.3 as an off-white foam. 1H-NMR (200 MHz, CDCl3): δ 1.50-1.67 (m, 2H), 1.80 (s, 3H), 2.94-3.20 (m, 4H), 3.32-3.46 (m, 1H), 3.50-3.70 (m, 2H), 3.80-3.95 (m, 2H), 4.47 (s, 2H), 5.72 (brs, 1H), 6.22 (s, 1H), 6.81 (brs, 1H), 7.20-7.38 (m, 3H), 7.75-7.90 (m, 4H), 8.37-8.40 (m, 2H), 9.37 (brs, 1H); MS (ES): 574.1 [MH+].

Provenance & Evidence