N-[4-[(2-Amino-3-chloropyridin-4-yl)oxy]-3-fluorophenyl]-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

Base Information

• Chemical Name: N-[4-[(2-Amino-3-chloropyridin-4-yl)oxy]-3-fluorophenyl]-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
• CAS No.: 1025720-94-8
• Molecular Formula: C25H19ClF2N4O4
• Molecular Weight: 512.9
• Mol file: 1025720-94-8.mol

Synonyms:(S)-2-[4-[2-(4-amino-2-oxo-3,5,7-triazabicyclo[4.3.0]nona-1(6),3,8-trien-9-yl)ethyl]benzoyl]aminopentanedioic acid;1juj;LYA;Pemetrexed (INN);Pemetrexed acid;(S)-2-(4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioic acid;N-(4-(2-Amino-3-chloropyridin-4-yloxy)-3-fluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide;N-(4-(2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-D]pyrimidin-5-yl)ethyl)benzoyl)-L-glutamic acid;Alimta;查看更多英文别名收起

Chemical Property of N-[4-[(2-Amino-3-chloropyridin-4-yl)oxy]-3-fluorophenyl]-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

Chemical Property:

• Appearance/Colour: White to off-white solid
• Boiling Point: 667.9±55.0 °C(Predicted)
• PKA: 10.54±0.70(Predicted)
• PSA: 112.69000
• Density: 1.49
• LogP: 5.50370
• Solubility.: ≥25.65 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH

Purity/Quality:

98% min ^*data from raw suppliers

N-[4-[(2-Amino-3-chloro-4-pyridinyl)oxy]-3-fluorophenyl]-4-ethoxy-1-(4-fluorophenyl)-1,2-dihydro-2-oxo-3-pyridinecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-[4-[(2-amino-3-chloro-4-pyridinyl)oxy]-3-fluorophenyl]-4-ethoxy-1-(4-fluorophenyl)-1,2-dihydro-2-oxo-3-pyridinecarboxamide is a selective and orally efficacious Inhibitor of the Met Kinase superfami ly.

Technology Process of N-[4-[(2-Amino-3-chloropyridin-4-yl)oxy]-3-fluorophenyl]-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

There total 17 articles about N-[4-[(2-Amino-3-chloropyridin-4-yl)oxy]-3-fluorophenyl]-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-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: 74.0%

3-chloro-4-(4-(4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamido)-2-fluorophenoxy)picolinamide (1025721-14-5) → BMS-777607 (1025720-94-8,1196681-44-3)

Guidance literature:

With [bis(acetoxy)iodo]benzene; In water; ethyl acetate; acetonitrile; at 0 - 20 ℃; for 2h;

Reference yield: 68.0%

ethanol (64-17-5) + N-(4-((2-amino-3-chloropyridin-4-yl) oxy)-3-fluorophenyl)-1-(4-fluorophenyl)-4-iodo-2-oxo-1,2-dihydropyridine-3-carboxamide → BMS-777607 (1025720-94-8,1196681-44-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

Reference yield:

3,4-dichloropyridine (55934-00-4) → BMS-777607 (1025720-94-8,1196681-44-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / diethyl ether / 2 h / -78 - 0 °C

1.2: 0.17 h / -78 - 20 °C

2.1: triethylamine; diphenyl phosphoryl azide / toluene / 0.5 h / 20 °C

2.2: 4 h / 90 °C

3.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 0.5 h / 20 °C

3.2: 12 h / 170 °C

4.1: ammonium chloride; iron / water; ethanol / 3 h / 80 °C

5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.5 h / 0 - 20 °C

5.2: 2 h / 0 - 20 °C

6.1: sodium hydride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; diphenyl phosphoryl azide; iron; sodium hydride; ammonium chloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; ethanol; water; toluene;

upstream raw materials:

3-chloro-4-(4-(4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamido)-2-fluorophenoxy)picolinamide

3,4-dichloropyridine

3,4-dichloropyridine-2-carboxylic acid

3,4-dichloropyridine-2-carboxamide

Refernces

• 1、 Schroeder, Gretchen M.,An, Yongmi,Cai, Zhen-Wei,Chen, Xiao-Tao,Clark, Cheryl,Cornelius, Lyndon A. M.,Dai, Jun,Gullo-Brown, Johnni,Gupta, Ashok,Henley, Benjamin,Hunt, John T.,Jeyaseelan, Robert,Kamath, Amrita,Kim, Kyoung,Lippy, Jonathan,Lombardo, Louis J.,Manne, Veeraswamy,Oppenheimer, Simone,Sack, John S.,Schmidt, Robert J.,Shen, Guoxiang,Stefanski, Kevin,Tokarski, John S.,Trainor, George L.,Wautlet, Barri S.,Wei, Donna,Williams, David K.,Zhang, Yingru,Zhang, Yueping,Fargnoli, Joseph,Borzilleri, Robert M.. "Discovery of N-(4-(2-amino-3-chloropyridin-4-yloxy)-3-fluorophenyl)-4- ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (BMS-777607), a selective and orally efficacious inhibitor of the met kinase superfamily". supporting information; experimental part. p. 1251 - 1254. Retrieved 2009/12/07.