198904-84-6

Basic information

• Product Name: tert-Butyl [[4-(2-pyridinyl)phenyl]methylene]hydrazinecarboxylate
• Synonyms: [[4-(2-pyridinyl)phenyl]methylene]hydrazinecarboxylic acid 1,1-dimethylethyl ester;tert-Butyl [[4-(2-pyridinyl)phenyl]methylene]hydrazinecarboxylate;Hydrazinecarboxylic acid, [[4-(2-pyridinyl)phenyl]methylene]-, 1,1-dimethylethyl ester;[[4-(2-pyridinyl)phenyl]methylene]-, 1,1-dimethylethyl ester;Hydrazinecarboxylicacid,[[4-(2-pyridinyl)phenyl];N-1-Boc-N-2-[4-(2-pyridinyl)benzylidene]hydrazone;Hydrazinecarboxylic acid, [[4-(2-;pyridinyl)phenyl]methylene]-, 1,1-dimethylethyl ester
• CAS NO: 198904-84-6
• Molecular Formula: C₁₇H₁₉N₃O₂
• Molecular Weight: 297.35
• EINECS: 1312995-182-4
• Product Categories: Aromatics Compounds;Aromatics;Heterocycles
• Mol File: 198904-84-6.mol
• Article Data: 11

Chemical Properties

• Appearance: White solid
• Density: 1.1 g/cm³
• Refractive Index: 1.559
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Dichloromethane, Methanol
• PKA: 10.14±0.46(Predicted)
• CAS DataBase Reference: tert-Butyl [[4-(2-pyridinyl)phenyl]methylene]hydrazinecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl [[4-(2-pyridinyl)phenyl]methylene]hydrazinecarboxylate(198904-84-6)
• EPA Substance Registry System: tert-Butyl [[4-(2-pyridinyl)phenyl]methylene]hydrazinecarboxylate(198904-84-6)

Safety Data

• Hazardous Substances Data: 198904-84-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C17H19N3O2/c1-17(2,3)22-16(21)20-19-12-13-7-9-14(10-8-13)15-6-4-5-11-18-15/h4-12H,1-3H3,(H,20,21)/b19-12+

Upstream product

• 109-04-6 2-bromo-pyridine 
• 87199-17-5 4-formylphenylboronic acid, 
• 127406-56-8 4-(2'-pyridyl)benzaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 870-46-2 t-butoxycarbonylhydrazine 

Downstream Products

• 198904-86-8 1-[4-(pyridine-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane 
• 198904-87-9 1-[4-(pyridin-2-yl)phenyl]-4(S)-hydroxy-5(S)-2,5-diamino-6-phenyl-2-azahexane trihydrochloride 
• 198904-31-3 atazanavir 
• 229975-97-7 atazanavir sulphate 
• 198904-85-7 N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine 
• 4467-06-5 2-(4-methylphenyl)pyridine 

Relevant articles and documents

A scalable synthesis of biaryl unit of the HIV protease inhibitor atazanavir

Atazanavir is one of the most prescribed HIV-1 protease inhibitors approved by the FDA. It was the first protease inhibitor approved for once-a-day dosing to treat AIDS due to good oral bioa-vailability and favorable pharmacokinetic profile. This research aims to develop a new synthetic cost effective process for biaryl-hydrazine unit {tert-butyl 2-[4-(2-pyridinyl)benzyl]hydrazinecarboxylate} of atazanavir on a large scale. The synthesis involved palladium catalyzed Suzuki-Miyaura coupling of 2-chloropyridine and (4-cyanophenyl)boronic acid followed by DIBAL-H reduction of cyano group to aldehyde which is then treated with tert-butyl carbazate to furnish hydrazone subsequently in situ reduction with NaBH4. A large scale synthesis of biaryl-hydrazine unit of atazanavir was accomplished in three steps with 71% overall yield. We have developed a short and efficient synthesis of atazanavir key intermediate biaryl-hydrazine unit. The process does not require the usage of Grignard reagent, expensive catalyst, protection/deprotection of aldehyde moiety and catalytic hydrogenation.

Preparation method of tert-butyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate

The invention discloses a preparation method of tert-butyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate. The preparation method comprises the steps that 1, 4-(2-pyridyl)benzaldehyde, ethyl alcohol and tert-butyl carbazate are put into a reaction kettle, and stirring is started; 2, tert-butyl 2-2-[4-(2-pyridyl)benzal]hydrazinecarboxylate is obtained; 3, tert-butyl 2-2-[4-(2-pyridyl)benzal]hydrazinecarboxylate, ethyl alcohol and palladium carbon are put into the reaction kettle, and stirring is started; 4, a sodium formate solution is dropwise added into a solution obtained in the step 3; 5, after a reaction is completed, a finished product is obtained. The preparation method has the following advantages that the production steps are greatly reduced compared with the prior art, and meanwhile a produced by-product is single and easy to separate; absolute ethyl alcohol serving as a solvent can be recycled repeatedly, palladium carbon serving as a catalyst can be used multiple times through recycling and draining, the production cost is lowered, and the production benefit of an enterprise is improved.

A three step continuous flow synthesis of the biaryl unit of the HIV protease inhibitor Atazanavir

The development of multistep continuous flow reactions for the synthesis of important intermediates for the pharmaceutical industry is still a significant challenge. In the present contribution the biaryl-hydrazine unit of Atazanavir, an important HIV protease inhibitor, was prepared in a three-step continuous flow sequence in 74% overall yield. The synthesis involved Pd-catalyzed Suzuki-Miyaura cross-coupling, followed by hydrazone formation and a subsequent hydrogenation step, and additionally incorporates a liquid-liquid extraction step.