Trifluoroacetic acid → HCID 44160055, compound

Temperature

80 °C

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).

1. additionwas added to it
2. concentrationThe reaction mixture was concentrated
3. extractionextracted with ethyl acetate
4. concentrationThe organic layer was concentrated to dryness
5. customthe 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)

ORD record

ord-316e381351f94f449491cb52ed2df081

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115137B2