(E)-N-(4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide

Base Information

• Chemical Name: (E)-N-(4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide
• CAS No.: 848133-17-5
• Molecular Formula: C31H29ClFN5O3
• Molecular Weight: 574.054
• UNII: 39R3638KZ6
• DSSTox Substance ID: DTXSID20233873
• Wikidata: Q27256922
• Metabolomics Workbench ID: 153882
• ChEMBL ID: CHEMBL178654
• Mol file: 848133-17-5.mol

Synonyms:848133-17-5;HKI-357;HKI 357;(E)-N-(4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide;CHEMBL178654;UNII-39R3638KZ6;39R3638KZ6;(E)-N-[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]-3-cyano-7-ethoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide;SCHEMBL2203413;SCHEMBL2203420;DTXSID20233873;EX-A6770;YIB13317;BDBM50161908;AKOS022175080;DB13002;MS-30340;HY-103443;CS-0027900;A900842;Q27256922;(2E)-N-[[4-[[(3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]amino]-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-2-butenamide;(E)-N-(4-(3-CHLORO-4-((3-FLUOROBENZYL)OXY)ANILINO)-3-CYANO-7-ETHOXY-6-QUINOLINYL)-4-(DIMETHYLAMINO)-2-BUTENAMIDE;2-Butenamide, N-(4-((3-chloro-4-((3-fluorophenyl)methoxy)phenyl)amino)-3-cyano-7-ethoxy-6-quinolinyl)-4-(dimethylamino)-, (2E)-;4-Dimethylamino-but-2-enoic acid {4-[3-chloro-4-(3-fluoro-benzyloxy)-phenylamino]-3-cyano-7-ethoxy-quinolin-6-yl}-amide

Chemical Property of (E)-N-(4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide

Chemical Property:

• XLogP3: 6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 573.1942957
• Heavy Atom Count: 41
• Complexity: 915

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=C(C=C2C(=C1)N=CC(=C2NC3=CC(=C(C=C3)OCC4=CC(=CC=C4)F)Cl)C#N)NC(=O)C=CCN(C)C
• Isomeric SMILES: CCOC1=C(C=C2C(=C1)N=CC(=C2NC3=CC(=C(C=C3)OCC4=CC(=CC=C4)F)Cl)C#N)NC(=O)/C=C/CN(C)C
• Recent ClinicalTrials: Study Evaluating the Safety, Tolerability, and Pharmacokinetics (PK) of HKI-357 Administered Orally to Healthy Subjects

Technology Process of (E)-N-(4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide

There total 6 articles about (E)-N-(4-((3-Chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide 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: 80.0%

4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-amino-7-ethoxyquinoline-3-carbonitrile (848133-14-2) → (E)-N-(4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide (848133-17-5)

Guidance literature:

(E)-4-(dimethylamino)-2-butenoic acid hydrochloride; With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; at 0 - 30 ℃; for 2h;

4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-amino-7-ethoxyquinoline-3-carbonitrile; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; at 0 - 5 ℃; for 3 - 16h;

Reference yield: 80.0%

(2E)-(N,N-dimethylamino)-2-butenoyl chloride (1056149-69-9) + 4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-amino-7-ethoxyquinoline-3-carbonitrile (848133-14-2) → (E)-N-(4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide (848133-17-5)

Guidance literature:

(2E)-(N,N-dimethylamino)-2-butenoyl chloride; 4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-amino-7-ethoxyquinoline-3-carbonitrile; With 1-methyl-pyrrolidin-2-one; In tetrahydrofuran; for 3 - 16h;

With water; In tetrahydrofuran; at 40 ℃;

With sodium hydroxide; In tetrahydrofuran; water; pH=10 - 11;

Reference yield:

4-bromocrotonyl chloride (99083-25-7) + dimethyl amine (124-40-3) + 4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-amino-7-ethoxyquinoline-3-carbonitrile (848133-14-2) → (E)-N-(4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)-4-(dimethylamino)but-2-enamide (848133-17-5)

Guidance literature:

4-bromocrotonyl chloride; 4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-amino-7-ethoxyquinoline-3-carbonitrile; With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 ℃; for 2h;

dimethyl amine; With sodium iodide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm040159c

upstream raw materials:

4-bromocrotonyl chloride

dimethyl amine

4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-amino-7-ethoxyquinoline-3-carbonitrile

4-Chloro-7-ethoxy-6-nitro-quinoline-3-carbonitrile