Sovaprevir

Base Information

• Chemical Name: Sovaprevir
• CAS No.: 1001667-23-7
• Molecular Formula: C43H53N5O8S
• Molecular Weight: 799.989
• UNII: 2ND9V3MN6O
• DSSTox Substance ID: DTXSID00142994
• Wikipedia: Sovaprevir
• Wikidata: Q16892599
• NCI Thesaurus Code: C152411
• Metabolomics Workbench ID: 144490
• ChEMBL ID: CHEMBL2105750
• Mol file: 1001667-23-7.mol

Synonyms:SOVAPREVIR;1001667-23-7;Sovaprevir [USAN];ACH-0141625;Sovaprevir [USAN:INN];UNII-2ND9V3MN6O;2ND9V3MN6O;ACH-1625;Sovaprevir (USAN);2-Pyrrolidinecarboxamide, N-[(1R,2S)-1-[[(cyclopropylsulfonyl)amino]carbonyl]-2-ethenylcyclopropyl]-1-[(2S)-3,3-dimethyl-1-oxo-2-[2-oxo-2-(1-piperidinyl)ethyl]butyl]-4-[(7-methoxy-2-phenyl-4-quinolinyl)oxy]-, (2S,4R)-;SOVAPREVIR [INN];Prodrug of ACH-1095;SOVAPREVIR [WHO-DD];SCHEMBL1462843;CHEMBL2105750;DTXSID00142994;CHEBI:177769;AKOS040749544;DB12069;(2S,4R)-N-[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]-1-[(2S)-3,3-dimethyl-2-(2-oxo-2-piperidin-1-ylethyl)butanoyl]-4-(7-methoxy-2-phenylquinolin-4-yl)oxypyrrolidine-2-carboxamide;D10166;Q16892599;(2S,4R)-1-((2S)-2-TERT-BUTYL-4-OXO-4-(PIPERIDIN-1-YL)BUTANOYL)-N-((1R,2S)-1-((CYCLOPROPANESULFONYL)CARBAMOYL)-2-ETHENYLCYCLOPROPYL)-4-((7-METHOXY-2-PHENYLQUINOLIN-4-YL)OXY)PYRROLIDINE-2-CARBOXAMIDE;(2S,4R)-1-((S)-2-(tert-butyl)-4-oxo-4-(piperidin-1-yl)butanoyl)-N-((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)-4-((7-methoxy-2-phenylquinolin-4-yl)oxy)pyrrolidine-2-carboxamide;(2S,4R)-1-((S)-2-tert-butyl-4-oxo-4-(piperidin-1-yl)butanoyl)-N-((1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropyl)-4-(7-methoxy-2-phenylquinolin-4-yloxy)pyrrolidine-2-carboxamide;(2S,4R)-N-((1R,2S)-1-((Cyclopropylsulfonyl)carbamoyl)-2-ethenylcyclopropyl)-1-((2S)- 3,3-dimethyl-2-(2-oxo-2-(piperidin-1-yl)ethyl)butanoyl)-4-((7-methoxy-2-phenylquinolin- 4-yl)oxy)pyrrolidine-2-carboxamide;(2S,4R)-N-[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinyl-cyclopropyl]-1-[(2S)-3,3-dimethyl-2-[2-oxo-2-(1-piperidyl)ethyl]butanoyl]-4-[(7-methoxy-2-phenyl-4-quinolyl)oxy]pyrrolidine-2-carboxamide;(2S,4R)-N-[(1R,2S)-1-(cyclopropylsulonylcarbamoyl)-2-ethenylcyclopropyl]-1-[(2S)-3,3-dimethyl-2-(2-oxo-2-piperidin-1-ylethyl)butanoyl]-4-(7-methoxy-2-phenylquinolin-4-yl)oxypyrrolidine-2-carboxamide;2-Pyrrolidinecarboxamide, N-((1R,2S)-1-(((cyclopropylsulfonyl)amino)carbonyl)-2- ethenylcyclopropyl)-1-((2S)-3,3-dimethyl-1-oxo-2-(2-oxo-2-(1-piperidinyl)ethyl)butyl)-4-

Chemical Property of Sovaprevir

Chemical Property:

• PSA: 172.69000
• LogP: 6.73130
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 14
• Exact Mass: 799.36148484
• Heavy Atom Count: 57
• Complexity: 1610

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(CC(=O)N1CCCCC1)C(=O)N2CC(CC2C(=O)NC3(CC3C=C)C(=O)NS(=O)(=O)C4CC4)OC5=CC(=NC6=C5C=CC(=C6)OC)C7=CC=CC=C7
• Isomeric SMILES: CC(C)(C)[C@H](CC(=O)N1CCCCC1)C(=O)N2C[C@@H](C[C@H]2C(=O)N[C@@]3(C[C@H]3C=C)C(=O)NS(=O)(=O)C4CC4)OC5=CC(=NC6=C5C=CC(=C6)OC)C7=CC=CC=C7
• Recent ClinicalTrials: Safety, Tolerability, and Antiviral Activity of ACH-0141625 or Placebo in Combination With Peginterferon and Ribavirin in Hepatitis C Virus (HCV) Positive Participants
• Recent EU Clinical Trials: A phase IIa, randomized, double-blind (subject and investigator blind, sponsor open) placebo-controlled trial to evaluate the safety, tolerability and antiviral activity of oral ACH-0141625 in combination with pegylated interferon alfa-2a and ribavirin in two segments, after 28 days of dosing and, subsequently, after 12 weeks of dosing in subjects with chronic hepatitis C virus genotype 1.

Technology Process of Sovaprevir

There total 13 articles about Sovaprevir 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:

(1R,2S)-1-amino-N-(cyclopropylsulfonyl)-2-vinylcyclopropanecarboxamide hydrochloride (630421-49-7) + (2S,4R)-1-((S)-2-(tert-butyl)-4-oxo-4-(piperidin-1-yl)butanoyl)-4-((7-methoxy-2-phenylquinolin-4-yl)oxy)pyrrolidine-2-carboxylic acid → (2S,4R)-1-((S)-2-tert-butyl-4-oxo-4-(piperidin-1-yl)butanoyl)-N-((1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropyl)-4-(6-methoxy-3-phenylisoquinolin-1-yloxy)pyrrolidine-2-carboxamide (1001667-23-7)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 15h; Reagent/catalyst;

Reference yield:

C19H32N2O5 → (2S,4R)-1-((S)-2-tert-butyl-4-oxo-4-(piperidin-1-yl)butanoyl)-N-((1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropyl)-4-(6-methoxy-3-phenylisoquinolin-1-yloxy)pyrrolidine-2-carboxamide (1001667-23-7)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium hydroxide; water / tetrahydrofuran; methanol

2: potassium tert-butylate / dimethyl sulfoxide / 24 h / 20 °C

3: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C

With potassium tert-butylate; water; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

tert-butyl ((1R,2S)-1-{[(cyclopropylsulfonyl)amino]carbonyl}-2-vinylcyclopropyl)carbamate (630421-48-6) → (2S,4R)-1-((S)-2-tert-butyl-4-oxo-4-(piperidin-1-yl)butanoyl)-N-((1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropyl)-4-(6-methoxy-3-phenylisoquinolin-1-yloxy)pyrrolidine-2-carboxamide (1001667-23-7)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C

2: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C

With hydrogenchloride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; N,N-dimethyl-formamide;

upstream raw materials:

tert-butyl ((1R,2S)-1-{[(cyclopropylsulfonyl)amino]carbonyl}-2-vinylcyclopropyl)carbamate

(1R,2S)-1-amino-N-(cyclopropylsulfonyl)-2-vinylcyclopropanecarboxamide hydrochloride

L-4-hydroxyproline methyl ester hydrochloride

(S)-4-(tert-butoxy)-2-(1,1-dimethylethyl)-4-oxobutanoic acid

Refernces

• 1、 -. "NOVEL PROCESSES FOR PRODUCING SOVAPREVIR". . . Retrieved 2014/10/04.