Production Method 1

354813-14-2

86620-62-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  rt; 1 h, 80 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 3 - 4

Reference

Design, synthesis and biological evaluation of novel 1H-1,2,4-triazole, benzothiazole and indazole-based derivatives as potent FGFR1 inhibitors via fragment-based virtual screening

Liu, Jian; et al, Journal of Enzyme Inhibition and Medicinal Chemistry, 2020, 35(1), 72-84

Production Method 2

354813-14-2

86620-62-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  2 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified, rt

Reference

Strategies toward Discovery of Potent and Orally Bioavailable Proteolysis Targeting Chimera Degraders of Androgen Receptor for the Treatment of Prostate Cancer

Han, Xin ; et al, Journal of Medicinal Chemistry, 2021, 64(17), 12831-12854

Production Method 3

109-01-3

456-22-4

86620-62-4

Reaction Conditions

1.1 Solvents: Dimethyl sulfoxide ;  36 h, 80 °C

Reference

Synthesis and thermal rearrangement of tertiary amine oxides derived from substituted piperazine

Saeed, May S.; et al, Chemica Sinica, 2012, 3(2), 292-298

Production Method 4

109-01-3

451-46-7

86620-62-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethyl sulfoxide ;  14 - 25 h, 120 °C
2.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  3 - 5 h, 70 °C; 70 °C → rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified, 0 °C

Reference

Discovery of Substituted 1H-Pyrazolo[3,4-b]pyridine Derivatives as Potent and Selective FGFR Kinase Inhibitors

Zhao, Bin; et al, ACS Medicinal Chemistry Letters, 2016, 7(6), 629-634

Production Method 5

163210-97-7

86620-62-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  2 h, 60 °C
2.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  2 h, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified, rt

Reference

Strategies toward Discovery of Potent and Orally Bioavailable Proteolysis Targeting Chimera Degraders of Androgen Receptor for the Treatment of Prostate Cancer

Han, Xin ; et al, Journal of Medicinal Chemistry, 2021, 64(17), 12831-12854

Production Method 6

773137-71-6

86620-62-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  3 - 5 h, 70 °C; 70 °C → rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified, 0 °C

Reference

Discovery of Substituted 1H-Pyrazolo[3,4-b]pyridine Derivatives as Potent and Selective FGFR Kinase Inhibitors

Zhao, Bin; et al, ACS Medicinal Chemistry Letters, 2016, 7(6), 629-634

Production Method 7

109-01-3

619-58-9

86620-62-4

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide Catalysts: Nickel(2+), tris(2,2′-bipyridine-κN1,κN1′)-, bromide (1:2), (OC-6-11)- Solvents: Dimethylacetamide ;  3 - 6 h, rt

Reference

Expanding Reactivity in DNA-Encoded Library Synthesis via Reversible Binding of DNA to an Inert Quaternary Ammonium Support

Flood, Dillon T.; et al, Journal of the American Chemical Society, 2019, 141(25), 9998-10006

Production Method 8

34334-28-6

86620-62-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid ;  100 °C

Reference

3,4-Disubstituted azetidinones as selective inhibitors of the cysteine protease cathepsin K. Exploring P3 elements for potency and selectivity

Setti, Eduardo L.; et al, Bioorganic & Medicinal Chemistry Letters, 2005, 15(5), 1529-1534

Production Method 9

86620-49-7

86620-62-4

Reaction Conditions

Reference

Carboxylic acid derivatives and drugs containing them

, Federal Republic of Germany, , ,

Production Method 10

109-01-3

1194-02-1

86620-62-4

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  100 °C
2.1 Reagents: Hydrochloric acid ;  100 °C

Reference

3,4-Disubstituted azetidinones as selective inhibitors of the cysteine protease cathepsin K. Exploring P3 elements for potency and selectivity

Setti, Eduardo L.; et al, Bioorganic & Medicinal Chemistry Letters, 2005, 15(5), 1529-1534

Production Method 11

109-01-3

403-33-8

86620-62-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Dimethyl sulfoxide ;  rt → 110 °C; 10 h, 110 °C
2.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  rt; 1 h, 80 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 3 - 4

Reference

Design, synthesis and biological evaluation of novel 1H-1,2,4-triazole, benzothiazole and indazole-based derivatives as potent FGFR1 inhibitors via fragment-based virtual screening

Liu, Jian; et al, Journal of Enzyme Inhibition and Medicinal Chemistry, 2020, 35(1), 72-84

4-(4-Methylpiperazin-1-yl)benzoic acid Raw materials

• 1-Methylpiperazine
• methyl 4-piperazin-1-ylbenzoate
• butyl 4-(4-methylpiperazin-1-yl)benzoate
• 4-Fluorobenzonitrile
• 4-(4-Methylpiperazin-1-yl)benzonitrile
• Ethyl 4-fluorobenzoate
• 4-Fluorobenzoic acid
• 4-Fluorobenzoic Acid Methyl Ester
• 4-Iodobenzoic acid
• Benzoic acid,4-(4-methyl-1-piperazinyl)-, ethyl ester
• Methyl 4-(4-methylpiperazin-1-yl)benzoate

4-(4-Methylpiperazin-1-yl)benzoic acid Preparation Products

• 4-(4-Methylpiperazin-1-yl)benzoic acid (86620-62-4)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazinanes Phenylpiperazines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazinanes Piperazines Phenylpiperazines

• 5429-28-7(4-(Diethylamino)benzoic acid)
• 94038-26-3(4-(4-Benzylpiperazin-1-yl)benzoic acid)
• 85474-75-5(4-(Piperazin-1-yl)benzoic acid)
• 446831-28-3(3-(Piperazin-1-YL)benzoic acid)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)