N²-tert-butyl-6-cyclopropyl-7-(3-trifluoromethylphenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide

Base Information

• Chemical Name: N²-tert-butyl-6-cyclopropyl-7-(3-trifluoromethylphenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide
• CAS No.: 1352086-27-1
• Molecular Formula: C₂₃H₂₇F₃N₄O₂
• Molecular Weight: 448.488

Synonyms:N²-tert-butyl-6-cyclopropyl-7-(3-trifluoromethylphenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide

Chemical Property of N²-tert-butyl-6-cyclopropyl-7-(3-trifluoromethylphenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide

Chemical Property:

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Technology Process of N²-tert-butyl-6-cyclopropyl-7-(3-trifluoromethylphenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide

There total 6 articles about N²-tert-butyl-6-cyclopropyl-7-(3-trifluoromethylphenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide 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:

N2-tert-butyl-7-bromo-6-cyclopropyl-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide (1352087-57-0) + (meta-(trifluoromethyl)phenyl)boronic acid (1423-26-3) → N2-tert-butyl-6-cyclopropyl-7-(3-trifluoromethylphenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide (1352086-27-1)

Guidance literature:

With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; water; at 70 ℃; for 20h; Inert atmosphere;

Reference yield:

1-tert-butyl 3-methyl 4-cyclopropanecarbonyl-piperazine-1,3-dicarboxylate (1352087-49-0) → N2-tert-butyl-6-cyclopropyl-7-(3-trifluoromethylphenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide (1352086-27-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydroxide; water / methanol / 24 h

2.1: p-toluenesulfonyl chloride / Difluoromethane / 0.33 h

2.2: 0.33 h

3.1: N-Bromosuccinimide / dichloromethane / 1 h / -35 - -30 °C

4.1: chloro-trimethyl-silane / methanol / 18 h / Inert atmosphere

5.1: triethylamine / dichloromethane / 2 h / 0 °C

6.1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; tetrahydrofuran / 20 h / 70 °C / Inert atmosphere

With N-Bromosuccinimide; chloro-trimethyl-silane; water; sodium carbonate; triethylamine; p-toluenesulfonyl chloride; sodium hydroxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; methanol; Difluoromethane; dichloromethane; water; 6.1: Suzuki Coupling;

Reference yield:

tert-butyl 8-carbamoyl-6-cyclopropyl-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylate (1352087-51-4) → N2-tert-butyl-6-cyclopropyl-7-(3-trifluoromethylphenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide (1352086-27-1)

Guidance literature:

Multi-step reaction with 4 steps

1: N-Bromosuccinimide / dichloromethane / 1 h / -35 - -30 °C

2: chloro-trimethyl-silane / methanol / 18 h / Inert atmosphere

3: triethylamine / dichloromethane / 2 h / 0 °C

4: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; tetrahydrofuran / 20 h / 70 °C / Inert atmosphere

With N-Bromosuccinimide; chloro-trimethyl-silane; sodium carbonate; triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; methanol; dichloromethane; water; 4: Suzuki Coupling;

upstream raw materials:

N²-tert-butyl-7-bromo-6-cyclopropyl-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide

(meta-(trifluoromethyl)phenyl)boronic acid

1-tert-butyl 3-methyl 4-cyclopropanecarbonyl-piperazine-1,3-dicarboxylate

sodium 1-tert-butyl 4-cyclopropanecarbonyl-piperazine-1, 3-dicarboxylate

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