N-{2-[(cyclopentylamino)methyl]-4-methyl-1H-indol-5-yl}-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide

Base Information

Chemical Name:N-{2-[(cyclopentylamino)methyl]-4-methyl-1H-indol-5-yl}-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide
CAS No.:1314127-25-7
Molecular Formula:C₂₇H₃₃N₃O₃
Molecular Weight:447.577
Hs Code.:

Synonyms:N-{2-[(cyclopentylamino)methyl]-4-methyl-1H-indol-5-yl}-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide

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Chemical Property of N-{2-[(cyclopentylamino)methyl]-4-methyl-1H-indol-5-yl}-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide

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Technology Process of N-{2-[(cyclopentylamino)methyl]-4-methyl-1H-indol-5-yl}-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide

There total 7 articles about N-{2-[(cyclopentylamino)methyl]-4-methyl-1H-indol-5-yl}-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide 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: 61.0%

: 1314128-27-2
N-(2-formyl-4-methyl-1H-indol-5-yl)-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide

: 1003-03-8
Cyclopentamine

: 1314127-25-7
N-{2-[(cyclopentylamino)methyl]-4-methyl-1H-indol-5-yl}-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide

Guidance literature:: N-(2-formyl-4-methyl-1H-indol-5-yl)-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide; Cyclopentamine; With acetic acid; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 2h;

With sodium tris(acetoxy)borohydride; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 16h;

With sodium hydroxide; In 1-methyl-pyrrolidin-2-one; water; ethyl acetate; at 20 ℃;

Reference yield:

: 87392-07-2
(S)-tetrahydro-2-furoic acid

: 1314127-25-7
N-{2-[(cyclopentylamino)methyl]-4-methyl-1H-indol-5-yl}-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: sulfuric acid / 11 h / 22 - 75 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 10 °C

2.2: 2 - 4 °C

3.1: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 96 h / 20 - 25 °C

3.2: 2 h / 90 °C

3.3: Cooling with ice

4.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dmap / N,N-dimethyl-formamide / 17 h / 20 °C

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C

5.2: 1 h / Reflux

6.1: acetic acid / 1-methyl-pyrrolidin-2-one / 2 h / 20 °C

6.2: 16 h / 20 °C

6.3: 20 °C

With lithium aluminium tetrahydride; sulfuric acid; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; dmap; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide; toluene;

Reference yield:

: 99-76-3,156291-94-0
methyl 4-hydroxylbenzoate

: 1314127-25-7
N-{2-[(cyclopentylamino)methyl]-4-methyl-1H-indol-5-yl}-4-[(2S)-tetrahydrofuran-2-ylmethoxy]benzamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / 96 h / 20 - 25 °C

1.2: 2 h / 90 °C

1.3: Cooling with ice

2.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dmap / N,N-dimethyl-formamide / 17 h / 20 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C

3.2: 1 h / Reflux

4.1: acetic acid / 1-methyl-pyrrolidin-2-one / 2 h / 20 °C

4.2: 16 h / 20 °C

4.3: 20 °C

With lithium aluminium tetrahydride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; dmap; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide; toluene;