4-(6-CHLORO-PYRIDAZIN-3-YL)-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Chemical Properties

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Light brown to off-white Solid

Safety Information

Hazard Codes 

Xi

4-(6-CHLORO-PYRIDAZIN-3-YL)-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER Usage And Synthesis

Uses

4-(6-Chloropyridazin-3-yl)piperazine-1-carboxylic Acid tert-Butyl Ester

Synthesis

To 3,6-dichloropyridazine (57.3 g, 385 mmol) and N-BOC-piperazine (71.6 g, 358 mmol) in 1,4-dioxane (250 mL) was added N,N-diisopropylethylamine (66.9 mL, 385 mmol). The reaction mixture was stirred at 80 °C overnight. Upon completion of the reaction, the mixture was concentrated under reduced pressure. The concentrated residue was dissolved in ethyl acetate (3 L) and washed sequentially with 10% citric acid solution, water and saturated saline. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by recrystallization from ethyl acetate to give tert-butyl 4-(6-chloropyridazin-3-yl)piperazine-1-carboxylate as an off-white solid (101 g, 88% yield). The product was confirmed by 1H NMR (400 MHz, CDCl3) and mass spectrometry (ESI): 1H NMR δ 1.25 (9H, s), 3.26-3.47 (8H, m), 6.67 (1H, d, J = 9.6 Hz), 7.00 (1H, d, J = 9.6 Hz); MS (ESI) m/z: 299.0 [M + H]+.

References

[1] Patent: US2015/353542, 2015, A1. Location in patent: Paragraph 0539
[2] Patent: EP3305785, 2018, A1. Location in patent: Paragraph 0204; 0205
[3] Patent: WO2017/197051, 2017, A1. Location in patent: Page/Page column 299
[4] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5361 - 5379
[5] Patent: US2005/176722, 2005, A1. Location in patent: Page/Page column 19

4-(6-CHLORO-PYRIDAZIN-3-YL)-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER(492431-11-5)Related Product Information

• ETHYL 1-BOC-5-OXO-HEXAHYDRO-1H-AZEPINE-4-CARBOXYLATE
• 1-Boc-5-formylindoline
• 7-Bromo-1H-indole, N-BOC protected
• 1-(5-Bromo-3-pyridyl)-4-tert-butoxycarbonylpiperazine
• TERT-BUTYL 4-[2-(AMINOMETHYL)PHENYL]PIPERAZINE-1-CARBOXYLATE
• 1-Boc-4-(5-Methyl-1,3,4-oxadiazol-2-yl)piperidine
• 4-[(AMINOIMINOMETHYL)AMINO]-1-PIPERIDINECARBOXYLIC ACID 1,1-DIMETHYLETHYL ESTER MONOHYDROCHLORIDE
• 1-BOC-OCTAHYDRO-PYRROLO[3,4-B]PYRIDINE
• tert-butyl 4-hydroxy-2-oxopiperidine-1-carboxylate
• 1-Boc-4-chloro-3-formylindole
• TERT-BUTYL 5-METHYLSPIRO[INDOLINE-3,4'-PIPERIDINE]-1-CARBOXYLATE
• 1-BOC-6-CHLOROINDOLE
• TERT-BUTYL 6-BROMO-1H-INDOLE-1-CARBOXYLATE
• 1-(6-Pyridazinyl)piperazine
• 4-(6-CHLORO-PYRIDAZIN-3-YL)-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 3-CHLORO-6-(4-METHYL-1-PIPERAZINYL)PYRIDAZINE
• tert-Butyl 1-piperazinecarboxylate
• 1-(6-Chloropyridazino-3-yl)piperazine