Chemical Products Description
4-(6-Aminopyridin-3-yl)piperazine-1-carboxylic acid tert-butyl ester is a pharmaceutical intermediate, mainly used for the synthesis of pabuxirib raw material medicine. 4-(6-Aminopyridin-3-yl)piperazine-1-carboxylic acid tert-butyl ester is an organic synthesis intermediate and pharmaceutical intermediate, mainly used as a laboratory research and development and chemical medicine synthesis process.
Chemical Products Basic Attributes
Molecular Formula ：C14H22N4O2
Molecular Mass ：278.354
Exact Mass ：278.174286
PSA ：71.7 A^2
H-bond Acceptor ：5
H-bond Donor ：1
Chemical Products Characteristics
Density ：1.2±0.1 g/cm3
Melting Point ：130-132℃
Flash Point ：228.4±28.7 °C
Refractive Index ：1.569
HS Code ：2933990090
Chemical Products Production Methods
Step b): synthesis of 4-(6-Amino-pyridin-3-yl)-piperazine-1-carboxylic acid tert- butyl ester formula 4)Step b): A 10 L autoclave was charged with 328.2 g of nitro 1 -Boc-4-(6-nitro-3- pyridyl)piperazine (formula 3) (1 .064 mol, 1 .00 eq.) and 3.5 L MeOH. The system was purged with NA 500-mL bottle was purged with nitrogen and charged with 188a (3.1 g, 10 mmol), 10percent palladium on carbon (50percent wet, 1.0 g) and ethanol (100 mL). It was evacuated, charged with hydrogen gas, and stirred for 16 h at room temperature. The hydrogen was then evacuated and nitrogen was charged into the bottle. The catalyst was removed by filtration through a pad of Celite and the filtrate concentrated under reduced pressure to afford 188b (2.7 g, 97percent). MS: [M+H]A 500-mL bottle was purged with nitrogen and charged with 115a (3.1 g, 10 mmol), 10percent palladium on carbon (50percent wet, 1.0 g) and ethanol (100 mL). Example 101h 1-tert-Butoxycarbonyl-4-(6-nitro-3-pyridyl)pyridazine (9.8 g, 31.78 mmol), ferric chloride hexahydrate added in a 250 mL three-neck round bottom flask at room temperature (0.6 g, 2.22 mmol) activated carbon (1.77 g) and ethanol(150mL), heat up to 80 °C for 0.5h, cool down to 65 °C, slowly add hydrazine hydrate (4.5mL, 73.9mmol), continue to heat upThe reaction was stirred at 80 ° C for 14 h, filtered while hot, washed three times with ethanol, most of the ethanol was removed under reduced pressure, and a yellow solid was evaporated.Filtration, drying and recrystallization from ethanol gave yellow acicular solid 1-tert-butoxycarbonyl-4-(6-amino-3-pyridyl)pyridazine8.617 g, yield 97.4percent, purity 98.8percent.To a vessel was added 4-(6-nitro-pyridin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester (12.0 g, 1.0 equiv.) along with ethyl acetate (48 mL, 4.0 vol.). To the slurry was added 50percent water wet 5percent Pd/C (480 mg, 4percent w/w) and the vessel was purged three times with nitrogen. The vessel was purged three times with hydrogen and then pressurized to 50 psi hydrogen. The mixture was heated to 42-47°C and allowed to stir until hydrogen uptake ceased (at least 8 hours).The product mixture was filtered and washed with ethyl acetate (2 x 1.5 mL). The combined filtrate was concentrated under reduced pressure to a volume of 6 mL (2 vol.). To the solution was added n-heptane (54 mL, 4.5 vol.) and the mixture was distilled under reduced pressure to a volume of 6 mL (2 vol.). To the solution was added n-heptane (54 mL, 4.5 vol.). The resulting thick slurry was cooled to 20-25°C and allowed to stir for 2 hours. The slurry was filtered and the filter cake washed with n-heptane (36 mL, 3 vol.). The solids were allowed to dry overnight in a vacuum oven at 50-55°C. The 4-(6-amino-pyridin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester was isolated as a pale orange solid (10.4 g collected; -96percent yield).A suspension of tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate (15.4 g, 50 mmol) in CHN,N-Diisopropylethylamine (4.77g, 36.94mmol) was added to a solution of 82 5-bromo-2-nitropyridine (5.00g, 24.63mmol) and 100 tert-butyl piperazine-1-carboxylate (5.10g, 27.09mol) in 101 acetonitrile ([ACN] 30mL). The mixture was refluxed for 2h, cooled to RT, concentrated under a vacuum, and purified by silica gel column chromatography (from 102 PE/86 EA=1:1 to 103 DCM/87 MeOH=20:1) to obtain 104 tert-butyl 4-(6-nitropyridin-3-yl)piperazine-1-carboxylate (3.80g; yield, 50percent) as a yellow solid. Pd/C (100.0mg) was added to a solution of tert-butyl 4-(6-nitropyridin-3-yl) piperazine-1-carboxylate (925.0mg, 3.0mmol) in EA/MeOH (10 mL/10mL). The mixture was degassed by flushing with HStep 2 Add 100 ml of methanol, 0.10 g of 10percent palladium carbon to 100 ml of the reaction vessel, and add 1.8 g of 4-(6-nitropyridin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester.
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