(E)-N-cyclohexyl-3-ethylidene-5-(4-methoxybenzyl)-4-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-6-carboxamide

Base Information

• Chemical Name: (E)-N-cyclohexyl-3-ethylidene-5-(4-methoxybenzyl)-4-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-6-carboxamide
• CAS No.: 1447525-19-0
• Molecular Formula: C₂₈H₃₁N₃O₃
• Molecular Weight: 457.572

Synonyms:(E)-N-cyclohexyl-3-ethylidene-5-(4-methoxybenzyl)-4-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-6-carboxamide

Chemical Property of (E)-N-cyclohexyl-3-ethylidene-5-(4-methoxybenzyl)-4-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-6-carboxamide

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Technology Process of (E)-N-cyclohexyl-3-ethylidene-5-(4-methoxybenzyl)-4-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-6-carboxamide

There total 4 articles about (E)-N-cyclohexyl-3-ethylidene-5-(4-methoxybenzyl)-4-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-6-carboxamide 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: 70.0%

N-(2-(cyclohexylamino)-1-(1H-indol-4-yl)-2-oxoethyl)-N-(4-methoxybenzyl)but-2-ynamide (1447524-97-1) → (E)-N-cyclohexyl-3-ethylidene-5-(4-methoxybenzyl)-4-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-6-carboxamide (1447525-19-0)

Guidance literature:

With indium(III) triflate; In 1,2-dichloro-ethane; at 100 ℃; for 3h; regioselective reaction; Inert atmosphere;

DOI:10.1039/c3cc42704h

Reference yield:

4-formyl indole (1074-86-8) → (E)-N-cyclohexyl-3-ethylidene-5-(4-methoxybenzyl)-4-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-6-carboxamide (1447525-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium sulfate; methanol / 50 °C

2: indium(III) triflate / 1,2-dichloro-ethane / 3 h / 100 °C / Inert atmosphere

With indium(III) triflate; methanol; sodium sulfate; In 1,2-dichloro-ethane; 1: |Ugi Condensation;

DOI:10.1039/c3cc42704h

Reference yield:

Cyclohexyl isocyanide (931-53-3) → (E)-N-cyclohexyl-3-ethylidene-5-(4-methoxybenzyl)-4-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-6-carboxamide (1447525-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium sulfate; methanol / 50 °C

2: indium(III) triflate / 1,2-dichloro-ethane / 3 h / 100 °C / Inert atmosphere

With indium(III) triflate; methanol; sodium sulfate; In 1,2-dichloro-ethane; 1: |Ugi Condensation;

DOI:10.1039/c3cc42704h

upstream raw materials:

Cyclohexyl isocyanide

4-formyl indole

N-(2-(cyclohexylamino)-1-(1H-indol-4-yl)-2-oxoethyl)-N-(4-methoxybenzyl)but-2-ynamide

4-methoxy-benzylamine

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