(2R)-1-(6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide hydrochloride

Base Information

• Chemical Name: (2R)-1-(6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide hydrochloride
• CAS No.: 1346172-70-0
• Molecular Formula: C₂₅H₂₃ClF₃N₇O₃S*ClH
• Molecular Weight: 630.478
• Mol file: 1346172-70-0.mol

Synonyms:(2R)-1-(6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide hydrochloride

Chemical Property of (2R)-1-(6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-1-(6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide hydrochloride

There total 12 articles about (2R)-1-(6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide hydrochloride 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:

tert-butyl (3R)-4-(6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrazin-2-yl)-3-[(2,2,2-trifluoroethyl)carbamoyl]piperazine-1-carboxylate (1346172-68-6) → (2R)-1-(6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide hydrochloride (1346172-70-0)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 0 ℃; for 0.5h;

Reference yield:

(R)-piperazine-1,2,4-tricarboxylic acid 1-benzyl ester 4-tert-butyl ester (954388-33-1) → (2R)-1-(6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide hydrochloride (1346172-70-0)

Guidance literature:

Multi-step reaction with 5 steps

1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 18 h / 20 °C

2: hydrogen / palladium 10% on activated carbon / methanol / 1 h / Inert atmosphere

3: triethylamine / N,N-dimethyl-formamide / 19 h / 100 - 170 °C / Microwave irradiation

4: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 0.33 h / 120 °C / Microweve irradiation

5: hydrogenchloride / ethyl acetate / 0.5 h / 0 °C

With hydrogenchloride; hydrogen; sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon; In methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

5-chloro-2-pyridylamine (1072-98-6) → (2R)-1-(6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide hydrochloride (1346172-70-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: iodine; sulfuric acid; periodic acid / ethanol; water / 15 h / 80 °C

1.2: pH 9

2.1: triethylamine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 1.67 h / 20 - 40 °C / Inert atmosphere

3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 4 h / 80 °C / Inert atmosphere

4.1: bromine; acetic acid / 3 h / 90 °C

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.83 h / 0 °C / Inert atmosphere

5.2: 1.5 h / 0 - 25 °C

6.1: potassium acetate / palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,2-dimethoxyethane / 6 h / 86 °C / Inert atmosphere

7.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 0.33 h / 120 °C / Microweve irradiation

8.1: hydrogenchloride / ethyl acetate / 0.5 h / 0 °C

With hydrogenchloride; copper(l) iodide; sulfuric acid; potassium tert-butylate; bromine; iodine; potassium acetate; sodium hydride; sodium carbonate; acetic acid; periodic acid; triethylamine; bis-triphenylphosphine-palladium(II) chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; 1,2-dimethoxyethane; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

(R)-piperazine-1,2,4-tricarboxylic acid 1-benzyl ester 4-tert-butyl ester

5-chloro-2-pyridylamine

5-chloro-3-iodo-2-aminopyridine

2-amino-5-chloro-3-[(trimethylsilyl)ethynyl]pyridine