4-Methoxybenzenesulfonyl chloride → HCID 178492815, compound

Participants

Reaction Steps

The crude 5-phenyl-3-(4-piperidinyl)-1H-indazole-7-carboxamide hydrochloride (21.1 mg, 0.066 mmol) (Example 2) was suspended in dichloromethane (8 mL) and treated with diisopropylethyl amine (46 uL, 0.264 mmols), DMAP (8 mg, 0.065 mmol), and 4-(methyloxy)benzenesulfonyl chloride (21 mg, 0.1 mmols) at 0° C. After 12 hrs, the mixture was concentrated to dryness in vacuo at ambient temperature, treated with water (10 mL), and extracted with ethyl acetate (3×25 mL). The organic phase was washed with water, dried over MgSO4, filtered, and concentrated to give a light brown solid. This was purified via preparative HPLC eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) to give the title compound (16 mg, 55%).

Provenance & Evidence