Production Method 1

943606-83-5

943606-84-6

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: 1,2-Dichloroethane ;  rt; 3 h, rt → 70 °C

Reference

Isoquinoline derivatives as Raf kinase modulators and their preparation, pharmaceutical compositions and use in the treatment of cancer

, World Intellectual Property Organization, , ,

Production Method 2

943606-83-5

943606-84-6

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: 1,2-Dichloroethane ;  rt; 7 h, rt

Reference

Preparation of isoquinoline-5-carboxamide derivatives as protein kinase inhibitors

, Korea, , ,

Production Method 3

943606-83-5

943606-84-6

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: 1,2-Dichloroethane ;  rt; 7 h, reflux

Reference

Preparation of thieno[3,2-d]pyrimidine derivatives having inhibitory activity for protein kinases

, World Intellectual Property Organization, , ,

Production Method 4

943606-83-5

943606-84-6

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: Chloroform ;  rt; rt → 70 °C; 3 h, 70 °C

Reference

Preparation of nitrogen-containing bicyclic heteroaryl compounds as antitumor agents

, United States, , ,

Production Method 5

943606-83-5

943606-84-6

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: 1,2-Dichloroethane ;  rt; 3 h, rt → 70 °C

Reference

Selective Inhibitors of the Mutant B-Raf Pathway: Discovery of a Potent and Orally Bioavailable Aminoisoquinoline

Smith, Adrian L.; De Morin, Frenel F.; Paras, Nick A.; Huang, Qi; Petkus, Jeffrey K.; et al, Journal of Medicinal Chemistry, 2009, 52(20), 6189-6192

Production Method 6

943606-83-5

943606-84-6

Reaction Conditions

1.1 Reagents: Lithium chloride ,  Phosphorus oxychloride Solvents: Dimethylformamide ,  Acetonitrile ;  17 h, 35 - 45 °C; 1 h, 20 - 30 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  pH 7 - 8, < 30 °C; 1 h, 20 - 30 °C

Reference

Synthesis of a bis-mesylate salt of 4-amino-N-(1-((3-chloro-2-fluorophenyl)amino)-6-methylisoquinolin-5-yl)thieno[3,2-d]pyrimidine-7-carboxamide and intermediates

, World Intellectual Property Organization, , ,

Production Method 7

943606-83-5

943606-84-6

Reaction Conditions

1.1 Reagents: Lithium chloride ,  Phosphorus oxychloride Catalysts: Dimethylformamide Solvents: Acetonitrile ;  17 h, 35 - 45 °C

Reference

An Efficient Second-Generation Manufacturing Process for the pan-RAF Inhibitor Belvarafenib

Zell, Daniel ; Dalziel, Michael E.; Carrera, Diane E.; Stumpf, Andreas ; Bachmann, Stephan; et al, Organic Process Research & Development, 2021, 25(10), 2338-2350

1-chloro-6-methyl-5-nitro-isoquinoline Raw materials

• 6-methyl-5-nitro-2-oxido-isoquinolin-2-ium

1-chloro-6-methyl-5-nitro-isoquinoline Preparation Products

• 1-chloro-6-methyl-5-nitro-isoquinoline (943606-84-6)

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• 10296-47-6(3-Chloro-5-nitroisoquinoline)
• 1367810-55-6(1-Chloro-6-nitro-isoquinoline)
• 760179-81-5(3-Chloro-6-nitroisoquinoline)
• 23056-33-9(2-Chloro-4-methyl-5-nitropyridine)
• 53364-98-0(Phenanthridine,6-chloro-2-nitro-)
• 54965-59-2(2-chloro-4-methyl-6-nitroquinoline)
• 79055-56-4(2-chloro-3-methyl-4-nitropyridine)
• 1374652-50-2(3-Chloro-8-nitroisoquinoline)
• 97944-45-1(2-Chloro-5-methyl-4-nitropyridine)
• 58142-97-5(1-chloro-5-nitroisoquinoline)