Ammonia → HCID 16035377, compound

Participants

Reaction Steps

A solution of dimethyl sulfoxide (0.037 g) in dichloromethane (1 mL) was added to a solution of oxalyl chloride (0.030 g) in dichloromethane (10 mL) at −78° C. The reaction was stirred for 15 minutes and then a solution of N-(2-dimethylaminoethyl)-N-(2-hydroxyethyl)-3-phenethyloxy-propanamide (Example 14a), 0.067 g) in dichloromethane (1 mL+1 mL wash) was added and the reaction stirred for a further 15 minutes. Triethylamine (0.11 g) was added and the reaction mixture was allowed to warm to room temperature over a period of 1 hour. The mixture was subsequently diluted (dichloromethane, 30 mL), the organics washed with saturated sodium hydrogencarbonate solution (20 mL) and then brine (20 mL), dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give a crude aldehyde product which was used immediately. The crude product was dissolved in methanol (10 mL) and 7-(2-aminoethyl)-4-hydroxy-3H-benzothiazol-2-one hydrochloride (0.054 g) added along with acetic acid (0.1 mL) and water (0.1 mL). After stirring at room temperature for 30 minutes, sodium cyanoborohydride (0.014 g) was added and the reaction mixture was stirred overnight. Ammonia (7N in methanol, 1 mL) was added and the mixture was concentrated. The crude residue was purified by flash silica column chromatography eluting with 1% ammonia; 5%-7% methanol in dichloromethane to afford the titled compound as a white solid (0.012 g).

Provenance & Evidence