Sodium hydride → HCID 71557024, compound

Participants

Reaction Steps

To a solution of 2-(6-amino-9H-purin-9-yl)-4-chlorophenol (0.053 g, 0.2 mmol) in N,N-dimethylformamide (1 mL) was added sodium hydride (60% w/w dispersion in mineral oil, 0.009 g, 0.2 mmol) and the mixture was stirred for 1 h at ambient temperature. N-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.107 g, 0.24 mmol) was added and the mixture was stirred at ambient temperature for 16 h and partitioned between ethyl acetate (100 mL) and saturated aqueous ammonium chloride (20 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue obtained was dissolved in dichloromethane (3 mL) and trifluoroacetic acid (3 mL). The reaction mixture was stirred for 1 h at ambient temperature and concentrated in vacuo. The residue was purified by preparative reverse-phase HPLC to afford 4-(2-(6-amino-9H-purin-9-yl)-4-chlorophenoxy)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide as an off-white solid in 17% yield (0.018 g): 1H NMR (300 MHz, DMSO-d6) δ8.48 (br s, 1H), 8.39 (s, 1H), 8.17 (br s, 1H), 7.95-7.74 (m, 4H), 7.74-7.58 (m, 2H), 7.40 (d, J=8.4 Hz, 1H), 7.34-7.22 (m, 1H); MS (ES+) m/z 536.6 (M+1), 538.6 (M+1).

Provenance & Evidence