2-amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Base Information

• Chemical Name: 2-amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide
• CAS No.: 1092523-24-4
• Molecular Formula: C₁₂H₁₃ClN₄O₂
• Molecular Weight: 280.714
• Mol file: 1092523-24-4.mol

Synonyms:2-amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Chemical Property of 2-amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Chemical Property:

• Melting Point: 274-276oC (dec.)
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly, Heated), Ethyl Acetate (Slightly, Heated)

Purity/Quality:

2-?Amino-?7-?chloro-?1-?ethyl-?N-?methyl-?4-?oxo-?1,?4-?dihydro-?1,?8-?naphthyridine-?3-?carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 2-Amino-7-chloro-1-ethyl-1,4-dihydro-N-methyl-4-oxo-1,8-naphthyridine-3-carboxamide is an intermediate in the synthesis of SAR131675 (S139510), is a potent and selective VEGFR-3 inhibitor.

Technology Process of 2-amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

There total 5 articles about 2-amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-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: 94.0%

6-chloro-2-(ethylamino)pyridine-3-carbonyl fluoride (1092523-22-2) + N-methyl-2-cyanoacetamide (6330-25-2) → 2-amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide (1092523-24-4)

Guidance literature:

N-methyl-2-cyanoacetamide; With hydrogen; sodium hydride; In water; N,N-dimethyl-formamide; mineral oil; at 0 - 5 ℃; for 0.166667h;

6-chloro-2-(ethylamino)pyridine-3-carbonyl fluoride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃;

Reference yield: 57.0%

3-[6-chloro-2-(ethylamino)pyridin-3-yl]-2-cyano-3-hydroxy-N-methylprop-2-enamide (1092523-23-3) → 2-amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide (1092523-24-4)

Guidance literature:

In butan-1-ol; at 110 ℃; for 48h;

Reference yield:

2,6-dichloropyridine-3-carboxylic acid (38496-18-3) → 2-amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide (1092523-24-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: water / 10 h / 50 °C

2.1: pyridine; trifluoro-[1,3,5]triazine / dichloromethane

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C

3.2: 0 - 20 °C

4.1: butan-1-ol / 48 h / 110 °C

With pyridine; trifluoro-[1,3,5]triazine; sodium hydride; In dichloromethane; water; N,N-dimethyl-formamide; mineral oil; butan-1-ol;

upstream raw materials:

6-chloro-2-(ethylamino)pyridine-3-carbonyl fluoride

N-methyl-2-cyanoacetamide

3-[6-chloro-2-(ethylamino)pyridin-3-yl]-2-cyano-3-hydroxy-N-methylprop-2-enamide

2,6-dichloropyridine-3-carboxylic acid

Downstream raw materials:

Ethyl {4-[7-amino-8-ethyl-6-(methylcarbamoyl)-5-oxo-5,8-dihydro-1,8-naphthyridin-2-yl]phenyl}acetate

2-amino-1-ethyl-7-{4-[2-({[(2S)-1-ethyl-4,4-difluoropyrrolidin-2-yl]methyl}-amino)-2-oxoethyl]phenyl}-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

2-amino-1-ethyl-7-{4-[2-({[(2S,4R)-1-ethyl-4-fluoropyrrolidin-2-yl]methyl}-amino)-2-oxoethyl]phenyl}-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

2-amino-1-ethyl-N-methyl-7-{4-[2-({[4-(1-methylethyl)morpholin-3-yl]-methyl}amino)-2-oxoethyl]phenyl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide