Trifluoroacetic acid → HCID 44160055, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetate (500 mg, 1.63 mmol) in oxalyl chloride (2.0 g, 16.33 mmol) was stirred at 25° C. for 3 h. After completion of the reaction (monitored by LCMS), cyclohexyl amine (1.0 ml, excess) was added to it and the reaction mixture heated at 80° C. for 3 h. The reaction mixture was concentrated and basified with aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was concentrated to dryness and the resulting crude 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 obtain 10 mg (yield: 2.0%) of 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)-N-cyclohexylacetamide as TFA salt. 1H NMR (DMSO) 10.0 (bs, 1H), 8.30 (d, 1H), 7.60 (s, 1H), 7.5 (d, 1H), 7.21 (d, 1H), 4.80 (m, 2H), 4.6 (m, 1H), 4.30 (m, 1H), 3.80 (m, 1H), 3.41 (m, 2H), 3.10 (bs, 2H), 3.0 (s, 3H), 1.80-1.20 (m, 10H).

Provenance & Evidence