Imidazo[1,5-a]pyrazine-1,7(8H)-dicarboxylic acid, 3-bromo-5,6-dihydro-, 7-(1,1-dimethylethyl) ester

Base Information

• Chemical Name: Imidazo[1,5-a]pyrazine-1,7(8H)-dicarboxylic acid, 3-bromo-5,6-dihydro-, 7-(1,1-dimethylethyl) ester
• CAS No.: 1094091-46-9
• Molecular Formula: C12H16BrN3O4
• Molecular Weight: 346.181
• Mol file: 1094091-46-9.mol

Synonyms:3-bromo-7-(tert-butoxycarbonyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylic acid;

Chemical Property of Imidazo[1,5-a]pyrazine-1,7(8H)-dicarboxylic acid, 3-bromo-5,6-dihydro-, 7-(1,1-dimethylethyl) ester

Chemical Property:

• PSA: 84.66000
• LogP: 2.03240

Purity/Quality:

97% purity ^*data from raw suppliers

3-Bromo-7-[(tert-butoxy)carbonyl]-5H,6H,7H,8H-imidazo[1,5-a]pyrazine-1-carboxylicacid 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Imidazo[1,5-a]pyrazine-1,7(8H)-dicarboxylic acid, 3-bromo-5,6-dihydro-, 7-(1,1-dimethylethyl) ester

There total 7 articles about Imidazo[1,5-a]pyrazine-1,7(8H)-dicarboxylic acid, 3-bromo-5,6-dihydro-, 7-(1,1-dimethylethyl) ester 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: 76.0%

7-(tert-butyl) 1-methyl 3-bromo-5,6-dihydroimidazo[1,5-a]pyrazine-1,7(8H)-dicarboxylate (1094091-45-8) → 3-bromo-7-(tert-butoxycarbonyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylic acid (1094091-46-9)

Guidance literature:

7-(tert-butyl) 1-methyl 3-bromo-5,6-dihydroimidazo[1,5-a]pyrazine-1,7(8H)-dicarboxylate; With lithium hydroxide; water; In methanol; at 50 ℃;

With hydrogenchloride; In water; at 0 ℃; pH=3;

Reference yield:

methyl 5-((benzyl(2-chloroethyl)amino)methyl)-1H-imidazole-4-carboxylate → 3-bromo-7-(tert-butoxycarbonyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylic acid (1094091-46-9)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / acetonitrile / 6 h / 80 °C / Inert atmosphere

2: N-ethyl-N,N-diisopropylamine; 20% palladium hydroxide-activated charcoal; hydrogen / ethanol / 3 h / 4654.46 Torr

3: N-Bromosuccinimide / acetonitrile / 4 h / Inert atmosphere

4: lithium hydroxide; water / methanol / 2 h / 40 °C

With N-Bromosuccinimide; 20% palladium hydroxide-activated charcoal; water; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In methanol; ethanol; acetonitrile;

Reference yield:

methyl 7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylate (1094091-43-6) → 3-bromo-7-(tert-butoxycarbonyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylic acid (1094091-46-9)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine; 20% palladium hydroxide-activated charcoal; hydrogen / ethanol / 3 h / 4654.46 Torr

2: N-Bromosuccinimide / acetonitrile / 4 h / Inert atmosphere

3: lithium hydroxide; water / methanol / 2 h / 40 °C

With N-Bromosuccinimide; 20% palladium hydroxide-activated charcoal; water; hydrogen; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In methanol; ethanol; acetonitrile;

upstream raw materials:

7-(tert-butyl) 1-methyl 3-bromo-5,6-dihydroimidazo[1,5-a]pyrazine-1,7(8H)-dicarboxylate

methyl 7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylate

7-tert-butyl 1-methyl 5,6-dihydroimidazo[1,5-α]pyrazine-1,7(8H)-dicarboxylate

methyl 5-formyl-1H-imidazole-4-carboxylate

Downstream raw materials:

3-benzoyl-7-(tert-butoxycarbonyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylic acid

Refernces

• 1、 -. "SUBSTITUTED IMIDAZOHETEROCYCLES". Page/Page column 17; 18. . Retrieved 2009/01/24.