Dimethylformamide → HCID 86602720, compound

Participants

Reaction Steps

To a solution of (rac)-(cis)-3-(acetyloxy)-cyclopentaneacetic acid (770 mg, 4.1 mmol) and N,N-dimethylformamide (0.01 ml, 0.13 mmol) in dichloromethane (10 ml) were added oxalyl chloride (1.4 ml, 17 mmol) and the resulting solution stirred for 18 h at ambient temperature. After evaporation of the volatile components in vacuo, the residue was taken up in toluene (10 ml) and again evaporated to dryness. The obtained acid chloride was then dissolved in dichloromethane (20 ml) and subsequently treated with N-ethyl-diisopropyl amine (2.5 ml, 15 mmol) and 4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine (960 mg, 3.6 mmol). After stirring for 2 h at ambient temperature and another hour at 50° C., the mixture was cooled to room temperature and treated with saturated aqueous sodium hydrogen carbonate (15 ml) and extracted twice with dichloromethane (20 ml each). After drying over magnesium sulphate and evaporation of the solvents, flash chromatography (silica, eluent dichloromethane/ethyl acetate 85:15) afforded (rac)-(cis)-2-(3-acetoxy-cyclopentyl)-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-acetamide as off-white solid. Separation by preparative chiral HPLC (Chiralpack AD, eluent heptane/isopropanol 85:15) afforded the title compound as first eluting isomer. Light yellow solid (4% yield). MS: m/e=434(M+H+), mp 171-172° C.

Provenance & Evidence