Acetic Acid → HCID 15616352, compound

Participants

Reaction Steps

A solution of 2,3,4,5-tetrahydro-2-[[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]-1H-pyrido[4,3-b]indol-1-one (523 mg) in dry DMF (30 ml) was treated with sodium hydride (60% dispersion in oil; 46 mg) and stirred for 15 min. at 21° under nitrogen. Cyclopentyl bromide (298 mg) was then added dropwise, and the mixture was stirred for 1 h and then heated at reflux for 4 h. The solution was left at 21° for 2 days, and then treated with a mixture of acetic acid (7 ml), water (7 ml) and THF (8 ml). The resulting solution was heated at reflux for 4 h, then basified with 2N sodium hydroxide and extracted with dichloromethane (3×25 ml). The combined extracts were washed with water (2×50 ml), concentrated in vacuo and purified by FCC eluting with System A (100:8:1) to give the free base of the title compound (42 mg) as a solid. Maleate formation gave the title compound (38 mg), m.p. 180° (decomp.), t.l.c. (System A, 100:8:1) Rf 0.3.

Provenance & Evidence