Triethylamine → HCID 59684267, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-[3-(3-chlorophenyl)-7-((S)-3-hydroxy-2-methylpropoxy)-1-oxo-1H-isoquinolin-2-yl]-N-isopropylacetamide (319 mg, 0.720 mmol) and triethylamine (0.30 mL, 2.16 mmol) in dry DCM (7.0 mL) was cooled to 0° C. and methanesulfonyl chloride (67 μL, 0.86 mmol) was added dropwise via a syringe. The mixture was stirred for 1 h at 0° C., a second aliquot of methanesulfonyl chloride (25 μL, 0.32 mmol) was added, and stirring was continued 30 min at room temperature. The mixture was diluted with ethyl acetate (20 mL) and washed with 1 N HCl (aq.) (20 mL), sat. NaHCO3 (aq.) (20 mL) and brine (20 mL). The aqueous washes were back-extracted with ethyl acetate (20 mL), and the combined organic extracts were dried (MgSO4) and concentrated to give crude methanesulfonic acid (R)-3-[3-(3-chlorophenyl)-2-(isopropylcarbamoylmethyl)-1-oxo-1,2-dihydroisoquinolin-7-yloxy]-2-methylpropyl ester (316 mg, 0.720 mmol, 84%) as off-white solid.

Provenance & Evidence