4-(4-((R)-(4'-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)-N-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)benzamide

Base Information

• Chemical Name: 4-(4-((R)-(4'-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)-N-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)benzamide
• CAS No.: 1357576-38-5
• Molecular Formula: C₅₀H₅₇ClF₃N₅O₇S₄
• Molecular Weight: 1060.74

Synonyms:4-(4-((R)-(4'-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)-N-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)benzamide

Chemical Property of 4-(4-((R)-(4'-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)-N-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)benzamide

Chemical Property:

Purity/Quality:

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Technology Process of 4-(4-((R)-(4'-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)-N-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)benzamide

There total 14 articles about 4-(4-((R)-(4'-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)-N-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)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: 69.0%

[4-((R)-3-morpholin-4-yl-1-phenylsulfanyl-methyl-propylamino)-3-trifluoromethanesulfonyl]benzenesulfonamide (1027345-12-5) + 4-(4-((R)-(4'-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)benzoic acid (1357576-37-4) → 4-(4-((R)-(4'-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)-N-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)benzamide (1357576-38-5)

Guidance literature:

4-(4-((R)-(4'-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)benzoic acid; With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 18 - 25 ℃; for 0.166667h; Inert atmosphere;

[4-((R)-3-morpholin-4-yl-1-phenylsulfanyl-methyl-propylamino)-3-trifluoromethanesulfonyl]benzenesulfonamide; In dichloromethane; at 18 - 25 ℃;

Reference yield:

tert-butyl 4-[(E)-{[(S)-2-methylpropane-2-sulfinyl]imino}methyl]piperidine-1-carboxylate (1097880-26-6) → 4-(4-((R)-(4'-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)-N-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)benzamide (1357576-38-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: TurboGrignard / tetrahydrofuran / 2 h / -15 °C

1.2: -15 °C

2.1: potassium phosphate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / toluene; water / 5 h / 100 °C

3.1: dichloromethane / 1 h / 18 - 25 °C

4.1: caesium carbonate / ruphos; chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct / ethanol / 1.5 h / 110 °C

5.1: Chiralpak AD column Column / ethanol; carbon dioxide / Resolution of diastereomers

6.1: water; lithium hydroxide / tetrahydrofuran; methanol / 40 °C

6.2: 0 °C / pH ~ 2

7.1: dmap; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 18 - 25 °C / Inert atmosphere

7.2: 18 - 25 °C

With dmap; potassium phosphate; TurboGrignard; water; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct; ruphos; In tetrahydrofuran; methanol; ethanol; dichloromethane; carbon dioxide; water; toluene;

Reference yield:

tert-butyl 4-((4'-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidine-1-carboxylate (1357577-24-2) → 4-(4-((R)-(4'-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)-N-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)benzamide (1357576-38-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dichloromethane / 1 h / 18 - 25 °C

2.1: caesium carbonate / ruphos; chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct / ethanol / 1.5 h / 110 °C

3.1: Chiralpak AD column Column / ethanol; carbon dioxide / Resolution of diastereomers

4.1: water; lithium hydroxide / tetrahydrofuran; methanol / 40 °C

4.2: 0 °C / pH ~ 2

5.1: dmap; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 18 - 25 °C / Inert atmosphere

5.2: 18 - 25 °C

With dmap; water; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct; ruphos; In tetrahydrofuran; methanol; ethanol; dichloromethane; carbon dioxide;

upstream raw materials:

4-fluoro-3-[(trifluoromethyl)sulfonyl]benzenesulfonamide

(R)-4-(4-morpholino-4-oxo-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)benzenesulfonamide

[4-((R)-3-morpholin-4-yl-1-phenylsulfanyl-methyl-propylamino)-3-trifluoromethanesulfonyl]benzenesulfonamide

4-(4-((R)-(4'-chlorobiphenyl-2-yl)((S)-1,1-dimethylethylsulfinamido)methyl)piperidin-1-yl)benzoic acid

Downstream raw materials:

tert-butyl 2-((R)-(4'-chlorobiphenyl-2-yl)(1-(4-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonylcarbamoyl)phenyl)piperidin-4-yl)methylamino)-2-oxoethyl(methyl)carbamate

tert-butyl 2-((R)-(4'-chlorobiphenyl-2-yl)(1-(4-(4-((R)-4-morpholino-1-(phenylthio)butan-2-yl amino)-3-(trifluoromethylsulfonyl)phenylsulfonylcarbamoyl)phenyl)piperidin-4-yl)methylamino)-2-oxoethylcarbamate

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