(E)-N-(4-chloro-3-cyano-7-ethoxyquinolin-6-yl)-4-(diMethylaMino)but-2-enaMide

Base Information

• Chemical Name: (E)-N-(4-chloro-3-cyano-7-ethoxyquinolin-6-yl)-4-(diMethylaMino)but-2-enaMide
• CAS No.: 848133-88-0
• Molecular Formula: C18H19ClN4O2
• Molecular Weight: 358.827
• Mol file: 848133-88-0.mol

Synonyms:

Chemical Property of (E)-N-(4-chloro-3-cyano-7-ethoxyquinolin-6-yl)-4-(diMethylaMino)but-2-enaMide

Chemical Property:

• PSA: 78.25000
• LogP: 3.28788

Purity/Quality:

99% ^*data from raw suppliers

(2E)-N-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl)-4-(dimethylamino)-2-butenamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2E)-N-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl)-4-(dimethylamino)-2-butenamide was used in the study for preparation of disubstituted (arylamino)quinolinecarbonitriles as orally active, irreversible inhibitors of human epidermal growth factor receptor-2 kinase activity and antitumor agents.

Technology Process of (E)-N-(4-chloro-3-cyano-7-ethoxyquinolin-6-yl)-4-(diMethylaMino)but-2-enaMide

There total 3 articles about (E)-N-(4-chloro-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:

4-Chloro-7-ethoxy-6-nitro-quinoline-3-carbonitrile (214476-09-2) → 4-chloro-6-(5-(dimethylamino)-2-oxopent-3-enyl)-7-ethoxyquinoline-3-carbonitrile (848133-88-0)

Guidance literature:

Multi-step reaction with 2 steps

1: iron; AcOH; NaOAc / methanol / Heating

2: 7.97 g / 1-methyl-pyrrolidin-2-one / 2.5 h / 0 - 20 °C

With sodium acetate; iron; acetic acid; In 1-methyl-pyrrolidin-2-one; methanol;

DOI:10.1021/jm040159c

Reference yield:

(E)-4-(dimethylamino)-2-butenoic acid hydrochloride (1130155-48-4) → 4-chloro-6-(5-(dimethylamino)-2-oxopent-3-enyl)-7-ethoxyquinoline-3-carbonitrile (848133-88-0)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride; DMF / acetonitrile / 0.5 h / 60 °C

2: 7.97 g / 1-methyl-pyrrolidin-2-one / 2.5 h / 0 - 20 °C

With oxalyl dichloride; N,N-dimethyl-formamide; In 1-methyl-pyrrolidin-2-one; acetonitrile;

DOI:10.1021/jm040159c

Reference yield:

(2E)-(N,N-dimethylamino)-2-butenoyl chloride (1056149-69-9) + 6-amino-4-chloro-7-ethoxyquinoline-3-carbonitrile (848133-87-9) → 4-chloro-6-(5-(dimethylamino)-2-oxopent-3-enyl)-7-ethoxyquinoline-3-carbonitrile (848133-88-0)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; at 0 - 20 ℃; for 2.5h;

DOI:10.1021/jm040159c

upstream raw materials:

(2E)-(N,N-dimethylamino)-2-butenoyl chloride

6-amino-4-chloro-7-ethoxyquinoline-3-carbonitrile

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

(E)-4-(dimethylamino)-2-butenoic acid hydrochloride

Downstream raw materials:

neratinib

neratinib

(E)-N-[4-(4-amino-3-chloroanilino)-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino)-2-butenamide

Refernces