Dimethyl Sulfoxide → HCID 178430848, compound

Participants

Reaction Steps

To a solution of oxalyl chloride (0.06 mL, 0.72 mmol) in anhydrous dichloromethane (1.0 mL) was added anhydrous dimethyl sulfoxide (0.09 mL, 1.20 mmol) dropwise at −78° C. under nitrogen atmosphere. The resulting solution was stirred for 10 minutes, followed by dropwise addition of a solution of N-(4-(4-methyl-4,5-dihydro-1H-imidazol-2-yl)pyridin-2-yl)benzamide (0.17 g, 0.60 mmol) in anhydrous dichloromethane (1.5 mL). The reaction mixture was stirred for 40 minutes, followed by the addition of anhydrous triethyl amine (0.33 mL, 2.38 mmol), warmed to ambient temperature during 3 hours and partitioned between water (15 mL) and dichloromethane (25 mL). The aqueous layer was extracted with dichloromethane (2×25 mL). The organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography eluting with ethyl acetate followed by methanol in ethyl acetate (1:25 ratio) to give N-(4-(4-methyl-1H-imidazol-2-yl)pyridin-2-yl)benzamide as a colorless solid (0.05 g, 38%): mp 133-135° C.; 1H NMR (300 MHz, DMSO-d6) δ 12.70 (s, 1H), 10.81 (s, 1H), 8.69 (s, 1H), 8.40 (d, J=5.3 Hz, 1H), 8.08-8.03 (m, 2H), 7.64-7.49 (m, 4H), 6.95 (br s, 1H), 2.24 (s, 3H); 13C NMR (75 MHz, CD3OD) δ 168.5, 154.1, 149.8, 144.5, 140.8, 135.6, 133.4, 129.8, 128.8, 116.9, 111.4, 11.6; MS (ES+) m/z 279.4 (M+1).

Provenance & Evidence