2-Cyclopentyl-N-{3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-benzo[b]thiophen-5-yl}-acetamide

Base Information

• Chemical Name: 2-Cyclopentyl-N-{3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-benzo[b]thiophen-5-yl}-acetamide
• CAS No.: 127973-89-1
• Molecular Formula: C₃₁H₃₂N₂O₅S₂
• Molecular Weight: 576.737

Synonyms:2-Cyclopentyl-N-{3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-benzo[b]thiophen-5-yl}-acetamide

Chemical Property of 2-Cyclopentyl-N-{3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-benzo[b]thiophen-5-yl}-acetamide

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Technology Process of 2-Cyclopentyl-N-{3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-benzo[b]thiophen-5-yl}-acetamide

There total 8 articles about 2-Cyclopentyl-N-{3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-benzo[b]thiophen-5-yl}-acetamide 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%

methyl 2-(aminosulfonyl)benzoate (88-19-7) + 4-<<5-(2-cyclopentylacetamido)benzothien-3-yl>methyl>-3-methoxybenzoic acid (127973-88-0) → 2-Cyclopentyl-N-{3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-benzo[b]thiophen-5-yl}-acetamide (127973-89-1)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 48h;

DOI:10.1021/jm00171a043

Reference yield:

methyl 5-nitrobenzo[b]thiophene-2-carboxylate (20699-86-9) → 2-Cyclopentyl-N-{3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-benzo[b]thiophen-5-yl}-acetamide (127973-89-1)

Guidance literature:

Multi-step reaction with 7 steps

1: aq. LiOH / tetrahydrofuran; methanol / 4 h

2: Cu⁰, quinoline / 170 - 180 °C

3: 30 percent / SnCl₄ / CH₂Cl₂ / 18 h / Heating

4: 54 percent / SnCl₂*2H₂O / ethanol / 2 h / Heating

5: 60 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 52 h

6: 96 percent / aq. LiOH / tetrahydrofuran; methanol / 4 h

7: 70 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h

With quinoline; dmap; lithium hydroxide; tin(IV) chloride; copper; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tin(ll) chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1021/jm00171a043

Reference yield:

5-nitrobenzo[b]thiophene (4965-26-8) → 2-Cyclopentyl-N-{3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-benzo[b]thiophen-5-yl}-acetamide (127973-89-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 30 percent / SnCl₄ / CH₂Cl₂ / 18 h / Heating

2: 54 percent / SnCl₂*2H₂O / ethanol / 2 h / Heating

3: 60 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 52 h

4: 96 percent / aq. LiOH / tetrahydrofuran; methanol / 4 h

5: 70 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h

With dmap; lithium hydroxide; tin(IV) chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tin(ll) chloride; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1021/jm00171a043

upstream raw materials:

methyl 2-(aminosulfonyl)benzoate

4-<<5-(2-cyclopentylacetamido)benzothien-3-yl>methyl>-3-methoxybenzoic acid

methyl 5-nitrobenzo[b]thiophene-2-carboxylate

5-nitrobenzo[b]thiophene

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