(4R)-4-[(2-chlorophenyl)sulfonyl]-1-{[1-(6-chloropyridin-3-yl)cyclopropyl]carbonyl}-N-(1-cyanocyclopropyl)-L-prolinamide

Base Information

• Chemical Name: (4R)-4-[(2-chlorophenyl)sulfonyl]-1-{[1-(6-chloropyridin-3-yl)cyclopropyl]carbonyl}-N-(1-cyanocyclopropyl)-L-prolinamide
• CAS No.: 1268444-84-3
• Molecular Formula: C₂₄H₂₂Cl₂N₄O₄S
• Molecular Weight: 533.435
• Mol file: 1268444-84-3.mol

Synonyms:

Chemical Property of (4R)-4-[(2-chlorophenyl)sulfonyl]-1-{[1-(6-chloropyridin-3-yl)cyclopropyl]carbonyl}-N-(1-cyanocyclopropyl)-L-prolinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-4-[(2-chlorophenyl)sulfonyl]-1-{[1-(6-chloropyridin-3-yl)cyclopropyl]carbonyl}-N-(1-cyanocyclopropyl)-L-prolinamide

There total 5 articles about (4R)-4-[(2-chlorophenyl)sulfonyl]-1-{[1-(6-chloropyridin-3-yl)cyclopropyl]carbonyl}-N-(1-cyanocyclopropyl)-L-prolinamide 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: 20.0%

1-(6-chloropyridin-3-yl)cyclopropanecarboxylic acid (854267-90-6) + (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide (1252638-10-0) → (4R)-4-[(2-chlorophenyl)sulfonyl]-1-{[1-(6-chloropyridin-3-yl)cyclopropyl]carbonyl}-N-(1-cyanocyclopropyl)-L-prolinamide (1268444-84-3)

Guidance literature:

With O-(1H-1,2,3-triazolo[4,5-b]pyridin-1-yl)-1,1,3,3-tetraethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 22 ℃; for 5h; Inert atmosphere;

DOI:10.1002/anie.201006781

Reference yield:

1-tert-butyl 2-methyl (2S)-4-[(2-chlorophenyl)sulfanyl]pyrrolidine-1,2-dicarboxylate → (4R)-4-[(2-chlorophenyl)sulfonyl]-1-{[1-(6-chloropyridin-3-yl)cyclopropyl]carbonyl}-N-(1-cyanocyclopropyl)-L-prolinamide (1268444-84-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 68 h / 0 - 22 °C / Inert atmosphere

2.1: water; lithium hydroxide / tetrahydrofuran / 1.5 h / 22 °C

2.3: pH 3

3.1: O-(1H-1,2,3-triazolo[4,5-b]pyridin-1-yl)-1,1,3,3-tetraethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.42 h / 22 °C / Inert atmosphere

3.2: 14.5 h / Inert atmosphere

4.1: formic acid / 2.5 h / 22 °C

4.2: 0 °C / pH 9

5.1: O-(1H-1,2,3-triazolo[4,5-b]pyridin-1-yl)-1,1,3,3-tetraethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 22 °C / Inert atmosphere

With O-(1H-1,2,3-triazolo[4,5-b]pyridin-1-yl)-1,1,3,3-tetraethyluronium hexafluorophosphate; formic acid; water; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hydroxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.201006781

Reference yield:

C17H22ClNO6S → (4R)-4-[(2-chlorophenyl)sulfonyl]-1-{[1-(6-chloropyridin-3-yl)cyclopropyl]carbonyl}-N-(1-cyanocyclopropyl)-L-prolinamide (1268444-84-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: water; lithium hydroxide / tetrahydrofuran / 1.5 h / 22 °C

1.3: pH 3

2.1: O-(1H-1,2,3-triazolo[4,5-b]pyridin-1-yl)-1,1,3,3-tetraethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.42 h / 22 °C / Inert atmosphere

2.2: 14.5 h / Inert atmosphere

3.1: formic acid / 2.5 h / 22 °C

3.2: 0 °C / pH 9

4.1: O-(1H-1,2,3-triazolo[4,5-b]pyridin-1-yl)-1,1,3,3-tetraethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 5 h / 22 °C / Inert atmosphere

With O-(1H-1,2,3-triazolo[4,5-b]pyridin-1-yl)-1,1,3,3-tetraethyluronium hexafluorophosphate; formic acid; water; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/anie.201006781

upstream raw materials:

1-(6-chloropyridin-3-yl)cyclopropanecarboxylic acid

(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide

tert-butyl (2S,4R)-4-[(2-chlorophenyl)sulfonyl]-2-{[(1-cyanocyclopropyl)amino]carbonyl}pyrrolidine-1-carboxylate