N-[(2S)-4-Methyl-1-[[(4R,7S)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide

Base Information

• Chemical Name: N-[(2S)-4-Methyl-1-[[(4R,7S)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide
• CAS No.: 362507-64-0
• Molecular Formula: C₂₇H₃₂N₄O₆S
• Molecular Weight: 540.64
• DSSTox Substance ID: DTXSID10436114
• Wikidata: Q72481949
• Pharos Ligand ID: 2XKBGUJPAQRT
• ChEMBL ID: CHEMBL202991
• Mol file: 362507-64-0.mol

Synonyms:362507-64-0;N-[(2S)-4-Methyl-1-[[(4R,7S)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide;Azepan-3-one compound 13;CHEMBL202991;SCHEMBL6215260;BDBM19781;DTXSID10436114;2-Benzofurancarboxamide, N-[(1S)-1-[[[(4R,7S)-hexahydro-7-methyl-3-oxo-1-(2-pyridinylsulfonyl)-1H-azepin-4-yl]amino]carbonyl]-3-methylbutyl]-;(2S)-2-(1-benzofuran-2-ylformamido)-4-methyl-N-[(4R,7S)-7-methyl-3-oxo-1-(pyridine-2-sulfonyl)azepan-4-yl]pentanamide;N-[(2S)-4-Methyl-1-{[(4R,7S)-7-methyl-3-oxo-1-(pyridine-2-sulfonyl)azepan-4-yl]amino}-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide

Chemical Property of N-[(2S)-4-Methyl-1-[[(4R,7S)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide

Chemical Property:

• Refractive Index: 1.629
• Density: 1.349 g/cm³
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 540.20425593
• Heavy Atom Count: 38
• Complexity: 967

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(C(=O)CN1S(=O)(=O)C2=CC=CC=N2)NC(=O)C(CC(C)C)NC(=O)C3=CC4=CC=CC=C4O3
• Isomeric SMILES: C[C@H]1CC[C@H](C(=O)CN1S(=O)(=O)C2=CC=CC=N2)NC(=O)[C@H](CC(C)C)NC(=O)C3=CC4=CC=CC=C4O3

Technology Process of N-[(2S)-4-Methyl-1-[[(4R,7S)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide

There total 73 articles about N-[(2S)-4-Methyl-1-[[(4R,7S)-7-methyl-3-oxo-1-pyridin-2-ylsulfonylazepan-4-yl]amino]-1-oxopentan-2-yl]-1-benzofuran-2-carboxamide 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: 97.0%

benzofuran-2-carboxylic acid{(S)-1-[(3S,4S,7R)-3-hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amide + Dess-Martin periodane (87413-09-0) → benzofuran-2-carboxylic acid{(S)-3-methyl-1-[(4S,7R)-7-methyl-3-oxo-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide (362505-84-8,362507-64-0)

Guidance literature:

In dichloromethane;

Reference yield: 85.0%

N-[(1S)-1-({[(3S,4S,7R)-3-hydroxy-7-methyl-1-(2-pyridinylsulfonyl)hexahydro-1H-azepin-4-yl]-amino}carbonyl)-3-methylbutyl]-1-benzofuran-2-carboxamide (362507-77-5) → Relacatib (362505-84-8,362507-64-0)

Guidance literature:

With acetic anhydride; In dimethyl sulfoxide; at 50 - 55 ℃; for 3h; Inert atmosphere; Large scale reaction;

DOI:10.1016/j.tet.2009.06.022

Reference yield: 32.0%

benzofuran-2-carboxylic acid {(S)-1-[3-hydroxy-7-methyl-1-(pyridine-2-sulfonyl)azepan-4-ylcarbamoyl]-3-methylbutyl}amide (403700-48-1) → Relacatib (362505-84-8,362507-64-0) + Benzofuran-2-carboxylic acid {(S)-3-methyl-1-[(4R,7S)-7-methyl-3-oxo-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-butyl}-amide (362507-64-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1021/jm050915u

upstream raw materials:

benzofuran-2-carboxylic acid {(S)-1-[3-hydroxy-7-methyl-1-(pyridine-2-sulfonyl)azepan-4-ylcarbamoyl]-3-methylbutyl}amide

2-methyl-2,3,4,7-tetrahydro-azepine-1-carboxylic acid benzyl ester

allyl(1-methylpent-4-enyl)carbamic acid benzyl ester

[(S)-1-(3-hydroxy-7-methylazepan-4-ylcarbamoyl)-3-methylbutyl]carbamic acid tert-butyl ester

Refernces

• 1、 Wang, Huan,Matsuhashi, Hayao,Doan, Brian D.,Goodman, Steven N.,Ouyang, Xi,Clark Jr., William M.. "Large-scale synthesis of SB-462795, a cathepsin K inhibitor: the RCM-based approaches". experimental part. p. 6291 - 6303. Retrieved 2009/12/04.
• 2、 Yamashita, Dennis S.,Marquis, Robert W.,Xie, Ren,Nidamarthy, Sirishkumar D.,Oh, Hye-Ja,Jeong, Jae U.,Erhard, Karl F.,Ward, Keith W.,Roethke, Theresa J.,Smith, Brian R.,Cheng,Geng, Xiaoliu,Lin, Fan,Offen, Priscilla H.,Wang, Bing,Nevins, Neysa,Head, Martha S.,Haltiwanger, R. Curtis,Sarjeant, Amy A. Narducci,Liable-Sands, Louise M.,Zhao, Baoguang,Smith, Ward W.,Janson, Cheryl A.,Gao, Enoch,Tomaszek, Thaddeus,McQueney, Michael,James, Ian E.,Gress, Catherine J.,Zembryki, Denise L.,Lark, Michael W.,Veber, Daniel F.. "Structure activity relationships of 5-, 6-, and 7-methyl-substituted azepan-3-one cathepsin K inhibitors". . p. 1597 - 1612. Retrieved 2007/10/03.