5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonyl chloride → HCID 10258200, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 8-(4-amino-benzyl)-3-cyclopropylmethyl-1-(2-fluoro-benzyl)-3,7-dihydro-purine-2,6-dione (2.0 g, 4.77 mmol) in pyridine (30 mL) under argon at 25° C. was treated with 5-chloro-1,3-dimethyl-pyrazole-4-sulfonyl chloride (1.31 g, 5.72 mmol). The reaction mixture was stirred at 25° C. for 24 h. The reaction mixture was then diluted with methylene chloride (500 mL) and washed with a 1.0N aqueous hydrochloric acid solution (3×100 mL). The combined water layers were extracted with methylene chloride (1×250 mL). The combined organics were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solid was stirred in acetonitrile (25 mL) for 20 min and then placed in the freezer for 1 h. The solids were collected by filtration, washed with cold acetonitrile, and dried in vacuo to afford 5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonic acid {4-[3-cyclopropylmethyl-1-(2-fluoro-benzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-amide (2.53 g, 87%) as a yellow solid; FAB-HRMS m/e calculated for C28H27ClFN7O4S (M+H)+ 612.1596, found 612.1585.

Provenance & Evidence