N,N-Dimethylglycine → HCID 56597424, compound

Participants

Reaction Steps

A mixture under Ar of (±)-5-bromo-1-(2-ethoxycarbonylmethoxy-5-fluoro-phenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (108 mg, 0.20 mmol, 1.00 eq.), methanesulfonamide (23 mg, 0.24 mmol, 1.20 eq.), N,N-dimethylglycine (4.3 mg, 0.04 mmol, 0.2 eq.), potassium phosphate tribasic (106 mg, 0.50 mmol, 2.5 eq.), and copper (I) iodide (7.6 mg, 0.04 mmol, 0.2 eq.) in DMF (2 mL) was stirred at 150° C. for 48 hours. The mixture was allowed to cool to r.t. and partitioned between AcOEt (25 mL) and H2O (25 mL). The layers were separated and the aq. phase was extracted with AcOEt (2×25 mL). The comb. org. phases were dried over MgSO4 and concentrated in vacuo. The residue was dissolved in DMF (1.0 mL). 1M aq. NaOH soln. (1.0 mL) was added. The mixture was stirred at r.t. for 18 hours. The solution was neutralized with 1M aq. HCl soln. (1.0 mL), then purified by prep. HPLC (column: Atlantis, 30×75 mm, 10 uM, acidic conditions, detection: UV/MS) to give the desired acid.

Provenance & Evidence