1-(2-Diethylcarbamoyl-ethyl)-3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indole-5-carboxylic acid cyclopentylmethyl-amide

Base Information

• Chemical Name: 1-(2-Diethylcarbamoyl-ethyl)-3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indole-5-carboxylic acid cyclopentylmethyl-amide
• CAS No.: 142535-37-3
• Molecular Formula: C₃₈H₄₆N₄O₆S
• Molecular Weight: 686.872
• Mol file: 142535-37-3.mol

Synonyms:1-(2-Diethylcarbamoyl-ethyl)-3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indole-5-carboxylic acid cyclopentylmethyl-amide

Chemical Property of 1-(2-Diethylcarbamoyl-ethyl)-3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indole-5-carboxylic acid cyclopentylmethyl-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2-Diethylcarbamoyl-ethyl)-3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indole-5-carboxylic acid cyclopentylmethyl-amide

There total 6 articles about 1-(2-Diethylcarbamoyl-ethyl)-3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indole-5-carboxylic acid cyclopentylmethyl-amide 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: 55.0%

methyl 2-(aminosulfonyl)benzoate (88-19-7) + 4-[5-(Cyclopentylmethyl-carbamoyl)-1-(2-diethylcarbamoyl-ethyl)-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid (142535-36-2) → 1-(2-Diethylcarbamoyl-ethyl)-3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indole-5-carboxylic acid cyclopentylmethyl-amide (142535-37-3)

Guidance literature:

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

DOI:10.1021/jm00091a010

Reference yield:

1H-Indole-5-carboxylic acid (1670-81-1,142396-03-0) → 1-(2-Diethylcarbamoyl-ethyl)-3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indole-5-carboxylic acid cyclopentylmethyl-amide (142535-37-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 12 h

2: 1.) Ag₂O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h

3: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF, RT, 8 h

4: 80 percent / aq. LiOH / methanol; tetrahydrofuran

5: 55 percent / Me₂N(CH₂)3N=C=NEt*HCl, DMAP / CH₂Cl₂

With dmap; lithium hydroxide; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00091a010

Reference yield:

cyclopentylmethylamine (6053-81-2) → 1-(2-Diethylcarbamoyl-ethyl)-3-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indole-5-carboxylic acid cyclopentylmethyl-amide (142535-37-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / 4-(dimethylamino)pyridine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 12 h

2: 1.) Ag₂O / 1.) dioxane, reflux, 1 h, 2.) dioxane, reflux, 3.5 h

3: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF, RT, 8 h

4: 80 percent / aq. LiOH / methanol; tetrahydrofuran

5: 55 percent / Me₂N(CH₂)3N=C=NEt*HCl, DMAP / CH₂Cl₂

With dmap; lithium hydroxide; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; silver(l) oxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00091a010

upstream raw materials:

methyl 2-(aminosulfonyl)benzoate

4-[5-(Cyclopentylmethyl-carbamoyl)-1-(2-diethylcarbamoyl-ethyl)-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid

1H-Indole-5-carboxylic acid

cyclopentylmethylamine

Refernces