Thionyl Chloride → HCID 10976788, compound

Participants

Reaction Steps

3-Benzo[1,3]dioxol-5-yl-propionic acid (2.50 g, 12.9 mmol) and thionyl chloride (20 mL, 274 mmol) were heated to 79° C. for 4 h then concentrated to afford 3-(benzo[d][1,3]dioxol-5-yl)propanoyl chloride as a brown oil. 2-(2-Imidazol-1-yl-6-methyl-pyrimidin-4-yl)-2-methyl-propylamine (100 mg, 0.432 mmol) and methylene chloride (20 mL) were added and the reaction mixture stirred at rt for about 2 h. The reaction mixture was filtered, filtrate washed with K2CO3 (100 mL, sat. aq.), and the organic layer was dried over Na2SO4. Filtration, concentration and purification using column chromatography gave 40 mg of 3-benzo[1,3]dioxol-5-yl-N-[2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-2-methyl-propyl]-propionamide as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.90 (s, 1H), 7.92 (s, 1H), 7.05 (s, 1H), 6.90 (s, 1H), 6.70 (m, 3H), 5.90 (s, 2H), 3.59 (d, 2H), 2.94 (t, 2H), 2.57 (s, 3H), 2.40 (t, 2H), 1.28 (s, 6H).

Provenance & Evidence