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

Base Information

• Chemical Name: N²-tert-butyl-6-chloro-7-(4-methoxyphenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide
• CAS No.: 1352086-75-9
• Molecular Formula: C₂₀H₂₅ClN₄O₃
• Molecular Weight: 404.896

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

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

Chemical Property:

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

There total 7 articles about N²-tert-butyl-6-chloro-7-(4-methoxyphenyl)-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:

8-carbamoyl-6-chloro-7-(4-methoxyphenyl)-1,2,3,4-dihydropyrrolo[1,2-a]pyrazine monohydrochloride (1352087-47-8) + Tert-butyl isocyanate (1609-86-5) → N2-tert-butyl-6-chloro-7-(4-methoxyphenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide (1352086-75-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

Reference yield:

tert-butyl 8-cyano-3,4-dihydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (1352087-38-7) → N2-tert-butyl-6-chloro-7-(4-methoxyphenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide (1352086-75-9)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium hydroxide; water; dihydrogen peroxide / methanol / 26 h / 55 °C

2: N-chloro-succinimide / dichloromethane / 6.66 h / -40 °C

3: N-Bromosuccinimide / ethyl acetate; Difluoromethane / 17 h / 0 - 20 °C

4: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; tetrahydrofuran / 20 h / 100 °C / Inert atmosphere

5: chloro-trimethyl-silane / methanol / 19 h

6: triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

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

Reference yield:

tert-butyl 8-carbamoyl-3,4-dihydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate (1352087-39-8) → N2-tert-butyl-6-chloro-7-(4-methoxyphenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxamide (1352086-75-9)

Guidance literature:

Multi-step reaction with 5 steps

1: N-chloro-succinimide / dichloromethane / 6.66 h / -40 °C

2: N-Bromosuccinimide / ethyl acetate; Difluoromethane / 17 h / 0 - 20 °C

3: caesium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; tetrahydrofuran / 20 h / 100 °C / Inert atmosphere

4: chloro-trimethyl-silane / methanol / 19 h

5: triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With N-chloro-succinimide; N-Bromosuccinimide; chloro-trimethyl-silane; caesium carbonate; triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; methanol; Difluoromethane; dichloromethane; water; ethyl acetate; 3: Suzuki Coupling;

upstream raw materials:

8-carbamoyl-6-chloro-7-(4-methoxyphenyl)-1,2,3,4-dihydropyrrolo[1,2-a]pyrazine monohydrochloride

Tert-butyl isocyanate

sodium 4-(tert-butyloxycarbonyl)-1-formylpiperazine-2-carboxylate

tert-butyl 8-carbamoyl-6-chloro-7-(4-methoxy-phenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate

Downstream raw materials:

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

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