Pyridine → 1-Methyl-1H-pyrazole-3-sulfonic acid (4-chloro-benzyl)-(3-hydroxy-phenyl)-amide

Participants

Reaction Conditions

Reaction Steps

Pyridine (520 μl, 6.4 mmol) was added to a stirred solution of 3-(4-chloro-benzylamino)-phenol (500 mg, 2.2 mmol) and 1-methylpyrazole-3-sulfonyl chloride (181 mg, 4.5 mmol) in anhydrous dichloromethane (22 ml). The reaction was stirred under nitrogen at 50° C. for 48 hours and then quenched with water (50 ml). The reaction was extracted with dichloromethane (3×25 ml), and the organics combined, washed with water (50 ml) and brine (50 ml), dried over anhydrous sodium sulphate and then concentrated in vacuo. The crude product was dissolved in a solution of tetrahydrofuran/methanol/water (1:1:1) (25 ml), treated with lithium hydroxide (271 mg, 6.45 mmol) and the mixture was stirred at 85° C. for 2 hours. The reaction was cooled, quenched with 2M hydrochloric acid (aq) until slightly acidic and extracted with ethyl acetate (2×50 ml). The organic extracts were combined, washed with water (100 ml), dried over anhydrous sodium sulphate and concentrated in vacuo to obtain a white solid (645 mg, 27% yield). HPLC retention time 5.59 min Mass spectrum (ES+) m/z 378 (M+H).

Provenance & Evidence