2-Amino-4-chloro-N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]benzamide

Base Information

• Chemical Name: 2-Amino-4-chloro-N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]benzamide
• CAS No.: 206350-07-4
• Molecular Formula: C19H18ClF2N5O2
• Molecular Weight: 421.834
• Mol file: 206350-07-4.mol

Synonyms:2-Amino-4-chloro-N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]benzamide;[R-(R*,R*)]-2-AMino-4-chloro-N-[2-(2,4-difluorophenyl)-2-hydroxy-1-Methyl-3-(1H-1,2,4-triazol-1-yl)propyl]benzaMide

Chemical Property of 2-Amino-4-chloro-N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]benzamide

Chemical Property:

• PKA: 11.61±0.29(Predicted)
• PSA: 109.55000
• Density: 1.46±0.1 g/cm3(Predicted)
• LogP: 3.65420
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

2-Amino-4-chloro-N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]benzamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Amino-4-chloro-N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]benzamide

There total 11 articles about 2-Amino-4-chloro-N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]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: 100.0%

(2R,3R)-3-Amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (127000-91-3) + 2-Amino-4-chlorobenzoic acid (89-77-0) → 2-Amino-4-chloro-N-[(1R,2R)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-benzamide (206350-07-4)

Guidance literature:

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; for 18h; Ambient temperature;

DOI:10.1021/jm9707277

Reference yield:

methyl (2S,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-nitrobutanoate → 2-Amino-4-chloro-N-[(1R,2R)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-benzamide (206350-07-4)

Guidance literature:

Multi-step reaction with 6 steps

1: hydrogen; palladium 10% on activated carbon / methanol / 12 h / 20 °C / 760.05 Torr

2: sodium tetrahydroborate / tetrahydrofuran; methanol / 12 h / 0 - 20 °C / Inert atmosphere

3: 1,2,4-Triazole; cyanomethylenetributyl-phosphorane / toluene / 3 h / 80 °C / Inert atmosphere

4: potassium carbonate / N,N-dimethyl-formamide / 11 h / 70 °C / Inert atmosphere

5: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C / Inert atmosphere

6: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

With 1,2,4-Triazole; 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; palladium 10% on activated carbon; hydrogen; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; cyanomethylenetributyl-phosphorane; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jacs.8b08236

Reference yield:

methyl (2S,3R)-3-((tert-butoxycarbonyl)amino)-2-(2,4-difluorophenyl)-2-hydroxybutanoate → 2-Amino-4-chloro-N-[(1R,2R)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl]-benzamide (206350-07-4)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium tetrahydroborate / tetrahydrofuran; methanol / 12 h / 0 - 20 °C / Inert atmosphere

2: 1,2,4-Triazole; cyanomethylenetributyl-phosphorane / toluene / 3 h / 80 °C / Inert atmosphere

3: potassium carbonate / N,N-dimethyl-formamide / 11 h / 70 °C / Inert atmosphere

4: hydrogenchloride / 1,4-dioxane / 2 h / 0 - 20 °C / Inert atmosphere

5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

With 1,2,4-Triazole; 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; cyanomethylenetributyl-phosphorane; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jacs.8b08236

upstream raw materials:

(2R,3R)-3-Amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol

2-Amino-4-chlorobenzoic acid

2,4-difluorobromobenzene

(2R,3R)-3-Azido-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Downstream raw materials:

albaconazole