Dimethylformamide → (S)-7-fluoro-N-((3-fluoro-4-methoxyphenyl)(1-methyl-1H-pyrazol-4-yl)methyl)-1,6-naphthyridine-2-carboxamide

Participants

Reaction Steps

A mixture of 74 (45 mg, 0.234 mmol), HATU (133.57 mg, 0.351 mmol), and DIPEA (0.123 mL, 0.703 mmol) in DMF (0.546 mL, 7.03 mmol) was stirred at RT for 5 min. To the solution was added in one portion (S)-(3-fluoro-4-methoxy-phenyl)-(1-methylpyrazol-4-yl)methanamine hydrochloride (50c) (76.36 mg, 0.281 mmol) and the reaction mixture was stirred at RT for 1 h. The reaction mixture was diluted with EtOAc (30 mL) and washed with water (20 mL). The organic layer was separated, dried (Na2SO4), filtered and concentrated in vacuo. The residue that was purified by SiO2 chromatography eluting a with an EtOAc/heptane gradient (0 to 100% EtOAc) to afford 80 mg (83%) of (S)-7-fluoro-N-((3-fluoro-4-methoxyphenyl)(1-methyl-1H-pyrazol-4-yl)methyl)-1,6-naphthyridine-2-carboxamide (76) as a yellow oil (80 mg, 83%), which was used in the next step without further purification.

Provenance & Evidence