Diisopropylethylamine → N-(1-{[4-Chloro-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-3-fluoro-4-pyridinecarboxamide

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Reaction Steps

To 3-fluoro-4-pyridinecarboxylic acid (27 mg, 0.191 mmol, Aldrich) was added a solution of HATU (24 mg, 0.189 mmol, Advanced asymmetrics) in DMF (0.5 ml), DIPEA (0.076 ml, 0.435 mmol) and then a solution of 1-{[4-chloro-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-amine (for a preparation see Intermediate 37)(40 mg, 0.145 mmol) in DMF (0.5 ml). The resulting yellow solution was stirred at ambient temperature overnight. Further amounts of HATU (72 mg, 0.189 mmol), 3-fluoro-4-pyridinecarboxylic acid (27 mg, 0.191 mmol) and DIPEA (0.076 ml, 0.435 mmol) were added. The reaction mixture was stirred at ambient temperature for a further 2 h. The reaction mixture was diluted with methanol and purified by MDAP on Sunfire C18 column (Method B) using Acetonitrile-Water with a Formic acid modifier. The solvent was evaporated in vacuo to give the title compound as a white solid (49 mg); LCMS: (System 4) MH+=399 tRET=2.82 min.

Provenance & Evidence