Ethanethiol, 2-(diethylamino)-, hydrochloride (1:1) → 2-{[(2-{[2-(Diethylamino)ethyl]sulfanyl}phenyl)sulfonyl]amino}-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-(diethylamino)ethanethiol hydrochloride (560 mg, 3.30 mmol) and 60% sodium hydride dispersion (224 mg, 10.18 mmol) was stirred in 3 mL of dry DMF until hydrogen evolution ceased. The mixture was treated with a solution of 2-([(2-fluorophenyl)sulfonyl]amino)-5,6,7,8-tetrahydro-1-napthalenecarboxylic acid methyl ester (200 mg, 0.55 mmol) in 1 mL of DMF, stirred at 70 to 75° C. overnight, and concentrated. The concentrate was purified by C18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product (200 mg, 78.7%). MS (APCI) m/e 462.8 (M+H)+; 1H NMR (400 MHz, CD3OD) δ 7.89 (dd, 1H), 7.65 (dd, 1H), 7.57 (dt, 1H) 7.34 (dt, 1H), 7.18 (d, 1H), 7.00 (d, 1H), 3.34-3.51 (m, 4H), 3.29 (m, 2H), 3.25 (q, 4H), 2.65-2.77 (m, 4H), 1.70 (m, 4H), 1.28 (t, 6H).

Provenance & Evidence