4-(5-AMINO-6-METHYL-2-PYRIDINYL)-1-PIPERAZINECARBOXYLIC ACID 1,1-DIMETHYLETHYL ESTER synthesis

Yield:936368-54-6 99%

Reaction Conditions:

with hydrogen;5% palladium over charcoal in tetrahydrofuran;methanol at 20; under 2068.65 - 2327.23 Torr; for 17 h;

Steps:

3

.Mix a slurry of 4-(6-methyl-5-nitro-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester (46.00 g, 142.7 mmol) in THF (750 mL) at room temperature with Pd/C (5% Aldrich, 3.04 g, 1.43 mmol) then place under a hydrogen atmosphere (Parr shaker, 40-45 psi) for 6 hours. Add MeOH (250 mL), and subject the slurry to an atmosphere of hydrogen for 4 hours at room temperature. Add additional catalyst(3.04 g), then place the mixture under hydrogen for 7 hours. Filter the mixture through a pad of Celite 521, washing with THF and MeOH then concentrate under reduced pressure to provide the title compound a pale pink solid. (41.58 g, 99% yield, MS(ES+): m/z = 293 [M+H]).

References:

WO2007/53394,2007,A1 Location in patent:Page/Page column 13