Triethylamine → tert-butyl (2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)(6-{[(1-methylcyclopropyl)carbonyl]amino}pyridin-3-yl)carbamate

Participants

Reaction Steps

tert-butyl (5-amino-4-methylpyridin-2-yl)(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)carbamate (80 mg, 0.17 mmol) from Step 2 of Example 30a, 1-methylcyclopropane-1-carboxylic acid (19.2 mg, 0.19 mmol), HATU (84 mg, 0.22 mmol) and triethylamine (68.5 mg, 0.68 mmol) were added in DMF (1.7 mL) at room temperature for 2 days. The reaction was added ethyl acetate (20 mL, washed with sodium bicarbonate saturated solution (10 mL), second wash with brine (10 mL). The organic phase was dried by magnesium sulfate, filtered, concentrated and purified by column chromatography through a 25 gram Biotage SNAP KP-Sil™ silica gel cartridge eluting with 30% ethyl acetate/hexanes to give the title compound as a pale yellow oil.

Provenance & Evidence