Water → HCID 11750392, compound

Participants

Reaction Conditions

Reaction Steps

3-(2,2-Difluoro-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)acetamido)benzoic acid 20 (407 mg, 1.02 mmol) was dissolved in SOCl2 (5.7 mL) and two drops of DMF were added at 0° C. This mixture was stirred at 0° C. for 1 h then evaporated under vacuum and the crude product was dissolved in CH2Cl2 (5 mL). B) Hydroxylamine hydrochloride (3.18 g, 45.7 mmol) was dissolved in THF (41.17 mL) and water (8.25 mL) and Et3N (8.25 mL) at 0° C., the mixture was stirred at 0° C. for 1 h. Solution A) was added at 0° C. via syringe in B) and the mixture was stirred at 0° C. for 10 min and abandoned at RT for 19 h. The mixture was evaporated and the residue obtained was extracted with CH2Cl2 (3×50 mL) and washed with water (50 mL). The organic layer was washed with brine (2×50 mL), dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography eluent (cyclohexane:EtOAc=98:02). 3-(2,2-Difluoro-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-7-yl)acetamido)-N-hydroxybenzamide EHT 9710 was obtained (40 mg, 10% yield) as an orange solid.

Provenance & Evidence