6-(TERT-BUTOXYCARBONYL)-5,6,7,8-TETRAHYDROPYRIDO[3,4-B]PYRAZINE-7-CARBOXYLIC ACID

Base Information

• Chemical Name: 6-(TERT-BUTOXYCARBONYL)-5,6,7,8-TETRAHYDROPYRIDO[3,4-B]PYRAZINE-7-CARBOXYLIC ACID
• CAS No.: 264623-57-6
• Molecular Formula: C13H17N3O4
• Molecular Weight: 279.29200
• Hs Code.: 2933990090
• Mol file: 264623-57-6.mol

Synonyms:(+-)-6-tert-Butoxycarbonyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-7-carboxylic Acid;(+/-)-N-tert-butoxycarbonyl-5,6,7,8-Tetrahydropyrido[3,4-b]pyrazine-7-carboxylic acid;

Chemical Property of 6-(TERT-BUTOXYCARBONYL)-5,6,7,8-TETRAHYDROPYRIDO[3,4-B]PYRAZINE-7-CARBOXYLIC ACID

Chemical Property:

• Vapor Pressure: 9.29E-09mmHg at 25°C
• Boiling Point: 446.6oC at 760 mmHg
• Flash Point: 223.9oC
• PSA: 92.62000
• Density: 1.309g/cm3
• LogP: 1.16090
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-(tert-Butoxycarbonyl)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-7-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-(TERT-BUTOXYCARBONYL)-5,6,7,8-TETRAHYDROPYRIDO[3,4-B]PYRAZINE-7-CARBOXYLIC ACID

There total 6 articles about 6-(TERT-BUTOXYCARBONYL)-5,6,7,8-TETRAHYDROPYRIDO[3,4-B]PYRAZINE-7-CARBOXYLIC ACID which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 49.3%

di-tert-butyl dicarbonate (24424-99-5) + ethyl 6-acetyl-7-ethoxycarbonyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-7-carboxylate (264623-82-7) → (+/-)-6-tert-butoxycarbonyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-7-carboxylic acid (264623-57-6)

Guidance literature:

ethyl 6-acetyl-7-ethoxycarbonyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-7-carboxylate; With hydrogenchloride; In water monomer; for 1h; Reflux;

With sodium hydroxide; In water monomer; pH=> 10 - 12; Cooling with ice;

di-tert-butyl dicarbonate; In 1,4-dioxane; water monomer; at 20 ℃; for 24h;

DOI:10.1021/acs.jmedchem.1c01564

Reference yield: 44.0%

di-tert-butyl dicarbonate (24424-99-5) + 5,6,7,8-tetrahydro-pyrido[3,4-b]pyrazine-7-carboxylic acid (764635-62-3) → (+/-)-6-tert-butoxycarbonyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-7-carboxylic acid (264623-57-6)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 20 ℃; for 72h;

DOI:10.1016/S0968-0896(02)00426-1

Reference yield:

(+/-)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-7-carboxylic acid hydrochloride (264623-56-5) + di-tert-butyl dicarbonate (24424-99-5) → (+/-)-6-tert-butoxycarbonyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-7-carboxylic acid (264623-57-6)

Guidance literature:

(+/-)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-7-carboxylic acid hydrochloride; di-tert-butyl dicarbonate; With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20 ℃; for 4h;

With hydrogenchloride; In 1,4-dioxane; water; pH=3;

upstream raw materials:

di-tert-butyl dicarbonate

5,6,7,8-tetrahydro-pyrido[3,4-b]pyrazine-7-carboxylic acid

2,3-dimethylpyrazine

2,3-bis(chloromethyl)pyrazine

Refernces

• 1、 Yoshiizumi, Kazuya,Yamamoto, Minoru,Miyasaka, Tomohiro,Ito, Yasuko,Kumihara, Hiroshi,Sawa, Masaaki,Kiyoi, Takao,Yamamoto, Takeshi,Nakajima, Fumio,Hirayama, Ryoichi,Kondo, Hirosato,Ishibushi, Etsuko,Ohmoto, Hiroshi,Inoue, Yoshimasa,Yoshino, Kohichiro. "Synthesis and structure-activity relationships of 5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-based hydroxamic acids as HB-EGF shedding inhibitors". . p. 433 - 450. Retrieved 2007/10/03.