(S)-N-(4-(((2S,5R)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidin-2-yl)methyl)phenyl)-2-(1H-pyrazol-1-yl)propanamide trifluoroacetic acid salt

Base Information

• Chemical Name: (S)-N-(4-(((2S,5R)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidin-2-yl)methyl)phenyl)-2-(1H-pyrazol-1-yl)propanamide trifluoroacetic acid salt
• CAS No.: 1190611-37-0
• Molecular Formula: C₂HF₃O₂*C₂₃H₂₇N₅O₂
• Molecular Weight: 519.524
• Mol file: 1190611-37-0.mol

Synonyms:

Chemical Property of (S)-N-(4-(((2S,5R)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidin-2-yl)methyl)phenyl)-2-(1H-pyrazol-1-yl)propanamide trifluoroacetic acid salt

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-(4-(((2S,5R)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidin-2-yl)methyl)phenyl)-2-(1H-pyrazol-1-yl)propanamide trifluoroacetic acid salt

There total 15 articles about (S)-N-(4-(((2S,5R)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidin-2-yl)methyl)phenyl)-2-(1H-pyrazol-1-yl)propanamide trifluoroacetic acid salt 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:

4-methoxybenzyl ((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(6-chloropyridin-3-yl)-6-(4-nitrophenyl)hex-5-yn-2-yl)carbamate (1190615-01-0) → (S)-N-(4-(((2S,5R)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidin-2-yl)methyl)phenyl)-2-(1H-pyrazol-1-yl)propanamide trifluoroacetic acid salt (1190611-37-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyrrolidine / N,N-dimethyl-formamide / 2 h / Inert atmosphere; Heating

1.2: 3 h / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 1.5 h / Inert atmosphere

3.1: sodium tris(acetoxy)borohydride / dichloromethane / 12 h / 0 - 25 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 °C / Inert atmosphere

5.1: hydrogen; palladium 10% on activated carbon; potassium acetate / methanol / 12 h / 2585.81 Torr

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere; Heating

7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 4 h / 25 °C / Inert atmosphere

7.2: chiral HPLC(Pirkle (R,R)-Whelk-O column / Inert atmosphere

8.1: dichloromethane / 2 h / 25 °C / Inert atmosphere

With pyrrolidine; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; potassium acetate; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm4017224

Reference yield:

4-methoxybenzyl ((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(6-chloropyridin-3-yl)-6-(4-nitrophenyl)-5-oxohexan-2-yl)carbamate (1190615-02-1) → (S)-N-(4-(((2S,5R)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidin-2-yl)methyl)phenyl)-2-(1H-pyrazol-1-yl)propanamide trifluoroacetic acid salt (1190611-37-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: trifluoroacetic acid / dichloromethane / 1.5 h / Inert atmosphere

2.1: sodium tris(acetoxy)borohydride / dichloromethane / 12 h / 0 - 25 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 °C / Inert atmosphere

4.1: hydrogen; palladium 10% on activated carbon; potassium acetate / methanol / 12 h / 2585.81 Torr

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere; Heating

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 4 h / 25 °C / Inert atmosphere

6.2: chiral HPLC(Pirkle (R,R)-Whelk-O column / Inert atmosphere

7.1: dichloromethane / 2 h / 25 °C / Inert atmosphere

With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; potassium acetate; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm4017224

Reference yield:

5-((R)-((tert-butyldimethylsilyl)oxy)((2R,5S)-5-(4-nitrobenzyl)pyrrolidin-2-yl)methyl)-2-chloropyridine (1190614-99-3) → (S)-N-(4-(((2S,5R)-5-((R)-hydroxy(pyridin-3-yl)methyl)pyrrolidin-2-yl)methyl)phenyl)-2-(1H-pyrazol-1-yl)propanamide trifluoroacetic acid salt (1190611-37-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 °C / Inert atmosphere

2.1: hydrogen; palladium 10% on activated carbon; potassium acetate / methanol / 12 h / 2585.81 Torr

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere; Heating

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 4 h / 25 °C / Inert atmosphere

4.2: chiral HPLC(Pirkle (R,R)-Whelk-O column / Inert atmosphere

5.1: dichloromethane / 2 h / 25 °C / Inert atmosphere

With palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; potassium acetate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm4017224

upstream raw materials:

4-methoxybenzyl ((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(6-chloropyridin-3-yl)-6-(4-nitrophenyl)hex-5-yn-2-yl)carbamate

4-methoxybenzyl ((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-1-(6-chloropyridin-3-yl)-6-(4-nitrophenyl)-5-oxohexan-2-yl)carbamate

5-((R)-((tert-butyldimethylsilyl)oxy)((2R,5S)-5-(4-nitrobenzyl)pyrrolidin-2-yl)methyl)-2-chloropyridine

(2S,5S)-tert-butyl 2-((R)-((tert-butyldimethylsilyl)oxy)(6-chloropyridin-3-yl)methyl)-5-(4-nitrobenzyl)pyrrolidine-1-carboxylate