2-Methylbenzoic acid → HCID 11541305, compound

Participants

Reaction Conditions

Reaction Steps

Carbonyl diimidazole (0.074 g 0.55 mmol) was added to a solution of 2-toluic acid (0.111 g, 0.67 mmol) in DMF (3 mL) and stirred at 22° C. for 1 h. To this, a solution of 4-chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester (free base of example 16, 0.2 g, 0.45 mmol) in DMF (2 mL) was added and stirred at 22° C. for 1 h. Solvent was removed and ice water (5 mL) was added. The solid separated was filtered, washed with water. The crude product obtained was purified by column chromatography (silica gel, ethyl acetate/pet ether) to obtain the title compound. Yield: 0.093 g (53%); mp: 201-204° C.; 1H NMR (DMSO-d6, 500 MHz): δ 2.23 (s, 3H, CH3), 2.64 (s, 3H, CH3), 3.15 (s, 2H, CH2), 3.28 (s, 2H, CH2), 3.34 (s, 2H, CH2), 3.39 (s, 2H, CH2), 3.87 (s, 3H, OCH3), 5.16 (s, 2H, CH2), 7.12 (s, 1H, Ar), 7.16 (s, 1H, Ar), 7.20 (m, 4H, Ar), 8.11 (s, 1H, Ar), 8.16 (s, 1H, Ar); MS: m/e (ES+) 555 (M+1).

Provenance & Evidence