4,4-difluoro-N-[(1S)-3-[(1S,5R)-3-(3-methyl-5-propan-2-yl-1,2,4-triazo l-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]-1-phenyl-propyl]cyclohexane-1-car boxamide

Base Information

• Chemical Name: 4,4-difluoro-N-[(1S)-3-[(1S,5R)-3-(3-methyl-5-propan-2-yl-1,2,4-triazo l-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]-1-phenyl-propyl]cyclohexane-1-car boxamide
• CAS No.: 674782-29-7
• Molecular Formula: C29H41F2N5O
• Molecular Weight: 513.6655464
• Mol file: 674782-29-7.mol

Synonyms:4,4-difluoro-N-[(1S)-3-[(1S,5R)-3-(3-methyl-5-propan-2-yl-1,2,4-triazo l-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]-1-phenyl-propyl]cyclohexane-1-car boxamide;Cyclohexanecarboxamide, 4,4-difluoro-N-((1S)-3-((3-exo)-3-(3-methyl-5-(1-methylethyl)-4H-1,2,4-triazol-4-yl)-8-azabicyclo(3.2.1)oct-8-yl)-1-phenylpropyl)-;Mvc;Selzentry;Uk 427857;Uk-427,857;Unii-md6p741W8a

Chemical Property of 4,4-difluoro-N-[(1S)-3-[(1S,5R)-3-(3-methyl-5-propan-2-yl-1,2,4-triazo l-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]-1-phenyl-propyl]cyclohexane-1-car boxamide

Chemical Property:

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,4-difluoro-N-[(1S)-3-[(1S,5R)-3-(3-methyl-5-propan-2-yl-1,2,4-triazo l-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]-1-phenyl-propyl]cyclohexane-1-car boxamide

There total 69 articles about 4,4-difluoro-N-[(1S)-3-[(1S,5R)-3-(3-methyl-5-propan-2-yl-1,2,4-triazo l-4-yl)-8-azabicyclo[3.2.1]oct-8-yl]-1-phenyl-propyl]cyclohexane-1-car boxamide 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: 91.0%

4,4-difluorocyclohexanecarboxylic acid (3-oxo-1-phenyl-propyl)-amide (376348-78-6) + exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate (423165-08-6,1545932-86-2) → maraviroc (376348-65-1,674782-29-7)

Guidance literature:

With sodium tris(acetoxy)borohydride; In ethyl acetate; at 0 - 15 ℃; for 2h; Inert atmosphere; Large scale;

DOI:10.1021/op800062d

Reference yield: 82.0%

(S)-3-((1R,3R,5S)-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl)-1-phenylpropan-1-amine (376348-71-9) + 4,4-difluorocyclohexane-1-carbonyl chloride (376348-75-3) → maraviroc (376348-65-1,674782-29-7)

Guidance literature:

With sodium carbonate; In dichloromethane; water; at 0 - 20 ℃;

DOI:10.1002/adsc.201000287

Reference yield: 75.0%

4,4-difluorocyclohexanecarboxylic acid (122665-97-8) + (S)-3-((1R,3R,5S)-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl)-1-phenylpropan-1-amine (376348-71-9) → maraviroc (376348-65-1,674782-29-7)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1002/ejoc.201800120

upstream raw materials:

4,4-difluorocyclohexanecarboxylic acid

(S)-3-((1R,3R,5S)-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl)-1-phenylpropan-1-amine

ethyl 4,4-difluorocyclohexane-1-carboxylate

tert-butyl (1S)-3-[3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-exo-8-azabicyclo[3.2.1]oct-8-yl]-1-phenylpropylcarbamate

Refernces

• 1、 Andrews, Keith G.,Denton, Ross M.,Hirst, David J.,Stoll, Emma L.,Tongue, Thomas,Valette, Damien. "A practical catalytic reductive amination of carboxylic acids". . p. 9494 - 9500. Retrieved 2020/10/02.
• 2、 Zhu, Yijun,Li, Hongyan,Lin, Kuaile,Wang, Bing,Zhou, Weicheng. "A novel and efficient asymmetric synthesis of anti-HIV drug maraviroc". . p. 1721 - 1728. Retrieved 2019/05/15.