3-{6-(2-Cyclopentyl-acetylamino)-1-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indol-3-yl}-propionamide

Base Information

Chemical Name:3-{6-(2-Cyclopentyl-acetylamino)-1-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indol-3-yl}-propionamide
CAS No.:142535-16-8
Molecular Formula:C₃₄H₃₈N₄O₆S
Molecular Weight:630.765
Hs Code.:

Synonyms:3-{6-(2-Cyclopentyl-acetylamino)-1-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indol-3-yl}-propionamide

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Chemical Property of 3-{6-(2-Cyclopentyl-acetylamino)-1-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indol-3-yl}-propionamide

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Technology Process of 3-{6-(2-Cyclopentyl-acetylamino)-1-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indol-3-yl}-propionamide

There total 6 articles about 3-{6-(2-Cyclopentyl-acetylamino)-1-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indol-3-yl}-propionamide 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: 41.0%

: 88-19-7
methyl 2-(aminosulfonyl)benzoate

: 142535-14-6
4-<<3-(2-carbamoylethyl)-6-(cyclopentylacetamido)indol-1-yl>methyl>-3-methoxybenzoic acid

: 142535-16-8
3-{6-(2-Cyclopentyl-acetylamino)-1-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indol-3-yl}-propionamide

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;
DOI:10.1021/jm00091a010

Reference yield:

: 142535-02-2
6-(cyclopentylacetamido)-3-formylindole

: 142535-16-8
3-{6-(2-Cyclopentyl-acetylamino)-1-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indol-3-yl}-propionamide

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / K₂CO₃ / dimethylformamide / 48 h

2: 90 percent / dioxane / 48 h / Heating

3: 92 percent / H₂ / 10percent Pd/C / methanol; tetrahydrofuran / 1.5 h / 2585.7 Torr

4: 85 percent / Et₃N, trimethylsilyl triflate / dioxane

5: 52 percent / con. ammonia (liq.), 4-(dimethylamino)pyridine / 8 h / 90 °C / 12928.7 Torr

6: 41 percent / Me₂N(CH₂)3N=C=NEt*HCl, DMAP / CH₂Cl₂

With dmap; trimethylsilyl trifluoromethanesulfonate; ammonia; hydrogen; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00091a010

Reference yield:

: 142535-07-7
tert-butyl 4-<<6-(cyclopentylacetamido)-3-formylindol-1-yl>methyl>-3-methoxybenzoate

: 142535-16-8
3-{6-(2-Cyclopentyl-acetylamino)-1-[2-methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1H-indol-3-yl}-propionamide

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / dioxane / 48 h / Heating

2: 92 percent / H₂ / 10percent Pd/C / methanol; tetrahydrofuran / 1.5 h / 2585.7 Torr

3: 85 percent / Et₃N, trimethylsilyl triflate / dioxane

4: 52 percent / con. ammonia (liq.), 4-(dimethylamino)pyridine / 8 h / 90 °C / 12928.7 Torr

5: 41 percent / Me₂N(CH₂)3N=C=NEt*HCl, DMAP / CH₂Cl₂

With dmap; trimethylsilyl trifluoromethanesulfonate; ammonia; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;
DOI:10.1021/jm00091a010