Triethylamine → HCID 67272458, compound

Participants

Reaction Steps

A solution of (3S)-methyl 7-(3-t-butyl-5-(3-(2,3-dichlorophenyl)ureido)-1H-pyrazol-1-yl)-2-(2,2,2-trifluoro-acetyl)-1,2,3,4-tetrahydroiso-quinoline-3-carboxylate from Example A42 (0.153 g, 0.250 mmol), methylamine hydrochloride (1.000 g, 14.8 mmol) and triethylamine (2.05 mL, 1.49 g, 14.7 mmol) in MeOH (5 mL) was stirred at 60° C. for 24 h. H2O was added (50 mL) and the mixture was extracted with CH2Cl2 (3×50 mL), dried (MgSO4) and concentrated. The residue was redissolved in CH2Cl2 (5 mL). Boc anhydride (0.055 g, 0.250 mmol) was added and the solution was stirred at RT for 30 min. The solvent was evaporated and the residue was purified by column chromatography to yield (3S)-t-butyl 7-(3-t-butyl-5-(3-(2,3-dichlorophenyl)ureido)-1H-pyrazol-1-yl)-3-(methyl-carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (52 mg, 34% yield) as a white solid. 1H NMR (400 MHz, acetone-d6) shows rotameric mixture. MS (EI) m/z: 615.2 (M+H+).

Provenance & Evidence