5-(1-benzyl-1H-indol-3-yl)-3-[(1-pyrrolidinylacetyl)amino]-2-thiophenecarboxamide

Base Information

• Chemical Name: 5-(1-benzyl-1H-indol-3-yl)-3-[(1-pyrrolidinylacetyl)amino]-2-thiophenecarboxamide
• CAS No.: 1440958-19-9
• Molecular Formula: C₂₆H₂₆N₄O₂S
• Molecular Weight: 458.584

Synonyms:5-(1-benzyl-1H-indol-3-yl)-3-[(1-pyrrolidinylacetyl)amino]-2-thiophenecarboxamide

Chemical Property of 5-(1-benzyl-1H-indol-3-yl)-3-[(1-pyrrolidinylacetyl)amino]-2-thiophenecarboxamide

Chemical Property:

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Technology Process of 5-(1-benzyl-1H-indol-3-yl)-3-[(1-pyrrolidinylacetyl)amino]-2-thiophenecarboxamide

There total 10 articles about 5-(1-benzyl-1H-indol-3-yl)-3-[(1-pyrrolidinylacetyl)amino]-2-thiophenecarboxamide 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: 98.0%

pyrrolidine (123-75-1) + 5-(1-benzyl-1H-indol-3-yl)-3-[(chloroacetyl)amino]-2-thiophenecarboxamide (1440958-08-6) → 5-(1-benzyl-1H-indol-3-yl)-3-[(1-pyrrolidinylacetyl)amino]-2-thiophenecarboxamide (1440958-19-9)

Guidance literature:

With potassium carbonate; In acetonitrile; for 1h; Reflux;

DOI:10.1016/j.ejmech.2013.03.022

Reference yield:

3-acetylindole (703-80-0) → 5-(1-benzyl-1H-indol-3-yl)-3-[(1-pyrrolidinylacetyl)amino]-2-thiophenecarboxamide (1440958-19-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: potassium hydroxide / ethanol / 20 °C

1.2: 0.08 h / 20 °C

2.1: trichlorophosphate / 0.5 h / 0 °C

2.2: 3 h / 0 - 20 °C

2.3: Cooling with ice

3.1: hydroxylamine hydrochloride; sodium acetate / ethanol / 6 h / 60 °C

4.1: di-2-pyridyl thionocarbonate; dmap / dichloromethane / 20 °C

5.1: sodium sulfide nonahydrate / N,N-dimethyl-formamide / 2 h / 50 °C

6.1: N,N-dimethyl-formamide / 2 h / 50 °C

7.1: sodium ethanolate / ethanol / 2 h / 50 °C

8.1: triethylamine / tetrahydrofuran / 2 h / 0 - 20 °C

9.1: potassium carbonate / acetonitrile / 1 h / Reflux

With dmap; sodium sulfide nonahydrate; hydroxylamine hydrochloride; sodium ethanolate; sodium acetate; potassium carbonate; di-2-pyridyl thionocarbonate; triethylamine; potassium hydroxide; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2.1: |Vilsmeier-Haack Formylation / 2.2: |Vilsmeier-Haack Formylation;

DOI:10.1016/j.ejmech.2013.03.022

Reference yield:

3-acetyl-1-benzyl-1H-indole (93315-38-9) → 5-(1-benzyl-1H-indol-3-yl)-3-[(1-pyrrolidinylacetyl)amino]-2-thiophenecarboxamide (1440958-19-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: trichlorophosphate / 0.5 h / 0 °C

1.2: 3 h / 0 - 20 °C

1.3: Cooling with ice

2.1: hydroxylamine hydrochloride; sodium acetate / ethanol / 6 h / 60 °C

3.1: di-2-pyridyl thionocarbonate; dmap / dichloromethane / 20 °C

4.1: sodium sulfide nonahydrate / N,N-dimethyl-formamide / 2 h / 50 °C

5.1: N,N-dimethyl-formamide / 2 h / 50 °C

6.1: sodium ethanolate / ethanol / 2 h / 50 °C

7.1: triethylamine / tetrahydrofuran / 2 h / 0 - 20 °C

8.1: potassium carbonate / acetonitrile / 1 h / Reflux

With dmap; sodium sulfide nonahydrate; hydroxylamine hydrochloride; sodium ethanolate; sodium acetate; potassium carbonate; di-2-pyridyl thionocarbonate; triethylamine; trichlorophosphate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: |Vilsmeier-Haack Formylation / 1.2: |Vilsmeier-Haack Formylation;

DOI:10.1016/j.ejmech.2013.03.022

upstream raw materials:

3-acetylindole

3-acetyl-1-benzyl-1H-indole

3-(1-benzyl-1H-indol-3-yl)-3-chloro-2-propenal oxime

3-(1-benzyl-1H-indol-3-yl)-3-chloro-2-propenenitrile

Downstream raw materials:

6-(1-benzyl-1H-indol-3-yl)-2-(1-pyrrolidinylmethyl)thieno[3,2-d]pyrimidin-4(3H)-one

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