Hydrochloric Acid → HCID 70944699, compound

Participants

Reaction Conditions

Reaction Steps

1-[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 185 mg, 0.516 mmol), 4-chloro-6-cyclopropyl-5-methylpyrimidine (Intermediate 52, 122 mg, 0.722 mmol) and DIPEA (0.180 ml, 1.032 mmol) were added together in N-methyl-2-pyrrolidone (NMP) (2 ml) and the resulting mixture was heated at 120° C. for 18 hours and allowed to cool to room temperature. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was separated, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by SP4 column chromatography eluting with a gradient of 0-100% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure. The residue, contaminated with NMP, was dissolved in methanol and passed down an SCX column (1 g) eluting with methanol, followed by 2M ammonia/methanol. Product containing fractions were combined and evaporated under reduced pressure. The resulting residue was dissolved in methanol (1 mL), treated with 1M hydrochloric acid in ether (0.05 ml, 0.050 mmol), the solvent removed under reduced pressure and the residue dried under high vacuum at 40° C. for 4 hours to give the title compound as a yellow solid, (10 mg);

Provenance & Evidence