N⁶-ethyl-N⁶-<4-<<4-(tert-butoxycarbonyl)piperazinyl>sulfonyl>benzyl>-6-aminobenzindol-2(1H)-one

Base Information

• Chemical Name: N⁶-ethyl-N⁶-<4-<<4-(tert-butoxycarbonyl)piperazinyl>sulfonyl>benzyl>-6-aminobenzindol-2(1H)-one
• CAS No.: 138384-96-0
• Molecular Formula: C₂₉H₃₄N₄O₅S
• Molecular Weight: 550.679

Synonyms:N⁶-ethyl-N⁶-<4-<<4-(tert-butoxycarbonyl)piperazinyl>sulfonyl>benzyl>-6-aminobenzindol-2(1H)-one

Chemical Property of N⁶-ethyl-N⁶-<4-<<4-(tert-butoxycarbonyl)piperazinyl>sulfonyl>benzyl>-6-aminobenzindol-2(1H)-one

Chemical Property:

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Technology Process of N⁶-ethyl-N⁶-<4-<<4-(tert-butoxycarbonyl)piperazinyl>sulfonyl>benzyl>-6-aminobenzindol-2(1H)-one

There total 7 articles about N⁶-ethyl-N⁶-<4-<<4-(tert-butoxycarbonyl)piperazinyl>sulfonyl>benzyl>-6-aminobenzindol-2(1H)-one 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: 47.0%

N6-ethyl 6-aminobenzindol-2(1H)-one (138384-95-9) + 1-(bromomethyl)-4-<<4-(tert-butoxycarbonyl)piperazinyl>sulfonyl>benzene (138384-98-2) → N6-ethyl-N6-<4-<<4-(tert-butoxycarbonyl)piperazinyl>sulfonyl>benzyl>-6-aminobenzindol-2(1H)-one (138384-96-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃;

DOI:10.1021/jm00082a006

Reference yield:

p-carboxyphenylsulfonyl chloride (10130-89-9) → N6-ethyl-N6-<4-<<4-(tert-butoxycarbonyl)piperazinyl>sulfonyl>benzyl>-6-aminobenzindol-2(1H)-one (138384-96-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 53 percent / DIEA / tetrahydrofuran / 1 h

2: 91 percent / K₂CO₃ / dimethylformamide / 0.33 h

3: 93 percent / 1 M DIBAL / tetrahydrofuran; hexane / 0.5 h

4: 96 percent / Ph₃P, CBr₄ / CH₂Cl₂ / 0.33 h

5: 47 percent / K₂CO₃ / dimethylformamide / 100 °C

With carbon tetrabromide; diisobutylaluminium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00082a006

Reference yield:

6-aminobenzindol-2(1H)-one hydrochloride (143301-38-6) → N6-ethyl-N6-<4-<<4-(tert-butoxycarbonyl)piperazinyl>sulfonyl>benzyl>-6-aminobenzindol-2(1H)-one (138384-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / dimethylformamide / 8 h / 70 - 100 °C

2: 47 percent / K₂CO₃ / dimethylformamide / 100 °C

With potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1021/jm00082a006

upstream raw materials:

N⁶-ethyl 6-aminobenzindol-2(1H)-one

1-(bromomethyl)-4-<<4-(tert-butoxycarbonyl)piperazinyl>sulfonyl>benzene

p-carboxyphenylsulfonyl chloride

6-aminobenzindol-2(1H)-one hydrochloride

Downstream raw materials:

N⁶-ethyl-N⁶-<4-(piperazinylsulfonyl)benzyl>-6-aminobenzindol-2(1H)-one

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