Isobutyric Acid → HCID 44160056, compound

Participants

Reaction Steps

A mixture of 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)ethanamine (100 mg, 0.411 mmol), isobutyric acid (36 mg, 0.411 mmol), N,N′-dicyclohexylcarbodiimide (93 mg, 0.452 mmol) and 4-dimethylaminopyridine (55 mg, 0.452 mmol) in dry dichloromethane (5.0 ml) were stirred at room temperature for 4 h. The reaction mixture was filtered through Celite and concentrated using rotary evaporator to afford 16 mg of N-(2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)ethyl)isobutyramide as TFA Salt after purification 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). 1H NMR (DMSO) 9.95 (bs, 1H), 7.9 (t, 1H), 7.4 (d 1H), 7.2 (s, 1H), 7.0 (d, 1H), 4.5-4.61 (m, 1H), 4.1-4.28 (m, 3H), 3.7-3.9 (m, 2H), 3.1-3.2 (m, 2H), 2.95 (s, 3H), 2.4 (s, 3H), 2.19-2.3 (m, 1H), 1.2-1.38 (m, 2H), 0.9 (d, 6H).

Provenance & Evidence