Pyridine → HCID 15958091, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 30 mg (0.075 mmol) 6-(4-benzyloxy-phenyl)-7-cyclohexyl-pyrazolo[1,5-a]pyrimidin-3-ylamine in 2 mL of acetonitrile (CH3CN) was added 0.018 mL (0.225 mmol) of pyridine (pyr), followed by 16 mg (0.2 mmol) of cyclopropylcarbonyl chloride or 19 mg (0.15 mmol) of ethanesulfonyl chloride, and 1 mg of dimethylaminopyridine (DMAP) and the resulting mixture was stirred at 60° C. overnight. Since analysis by LC-MS revealed product formation, the reaction mixture was concentrated to give a residue which was purified via reverse-phase chromatography to afford (after lyophilization) 17 mg (49% yield) of cyclopropanecarboxylic acid [6-(4-benzyloxy-phenyl)-7-cyclohexyl-pyrazolo[1,5-a]pyrimidin-3-yl]-amide (415) as a yellow solid or 17 mg (46% yield) of ethanesulfonic acid [6-(4-benzyloxy-phenyl)-7-cyclohexyl-pyrazolo[1,5-a]pyrimidin-3-yl]-amide (421) as a yellow solid as indicated by LC-MS—calcd for C29H30N4O2 [M++H]+: 467.24, found: 467.2; calcd for C27H30N4O3S [M++H]+: 491.2, found: 491.2.

Provenance & Evidence