Cyclohexanemethanol → HCID 44159222, compound

Participants

Reaction Steps

To a solution of 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetic acid (200 mg, 0.7 mmol) and cyclohexyl methanol (80 mg, 0.7 mmol) in dichloromethane (10 ml) were added N,N′-dicyclohexylcarbodiimide (177 mg, 0.86 mmol) and 4-dimethylaminopyridine (105 mg, 0.86 mmol) and the contents were stirred at 25 deg C. for 16 h. The reaction mixture was concentrated to dryness to obtain the crude compound which was purified by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 ml) to give 30 mg (11.3%) of cyclohexylmethyl 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetate as TFA salt. 1H NMR (DMSO) TFA SALT 10.39 (bs, 1H), 7.60 (s, 1H), 7.50 (d, 1H), 7.2 (d, 1H), 5.3-5.1 (dd, 2H), 4.70 (d, 1H), 4.30 (bs, 1H), 4.0 (d, 2H), 3.85 (bs, 1H), 3.50 (bs, 1H), 3.10 (s, 2H), 2.85 (s, 3H), 1.60-0.90 (m, 11H).

Provenance & Evidence