Production Method 1

78208-72-7

92933-47-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  3 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2, rt

Reference

Preparation of macrocyclic compounds as hepatitis C inhibitors and uses thereof in medicine

, World Intellectual Property Organization, , ,

Production Method 2

20577-64-4

92933-47-6

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Ethanol ;  2 h, reflux
1.2 Reagents: Sodium hydroxide Solvents: Water ;  overnight, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 2

Reference

Preparation of pyrazolo[4,3-d]pyrimidines for use in pharmaceutical compositions as kinase inhibitors and anticancer agents

, European Patent Organization, , ,

Production Method 3

78208-72-7

92933-47-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  rt → 50 °C; 3 h, 50 °C; cooled
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2

Reference

Preparation of pyrazolopyrimidinones as phosphodiesterase 9 (PDE9) inhibitors for treating type 2 diabetes, metabolic syndrome, and cardiovascular disease.

, United States, , ,

Production Method 4

92933-47-6

Reaction Conditions

Reference

Studies on hypolipidemic agents. II. Synthesis and pharmacological properties of alkylpyrazole derivatives

Seki, Kunio; Isegawa, Junichi; Fukuda, Minoru; Ohki, Masahiko, Chemical & Pharmaceutical Bulletin, 1984, 32(4), 1568-77

Production Method 5

78208-72-7

92933-47-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  overnight, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  < pH 7, rt

Reference

Pyrazole Derivatives as Partial Agonists for the Nicotinic Acid Receptor

van Herk, T.; Brussee, J.; van den Nieuwendijk, A. M. C. H.; van der Klein, P. A. M.; Ijzerman, A. P.; et al, Journal of Medicinal Chemistry, 2003, 46(18), 3945-3951

Production Method 6

78208-72-7

92933-47-6

Reaction Conditions

1.1 Reagents: Lithium hydroxide Solvents: Methanol ,  Tetrahydrofuran ,  Water ;  3 h, rt → 80 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, rt

Reference

Fluorinated pyrazole acids are agonists of the high affinity niacin receptor GPR109a

Skinner, Philip J.; Cherrier, Martin C.; Webb, Peter J.; Shin, Young-Jun; Gharbaoui, Tawfik; et al, Bioorganic & Medicinal Chemistry Letters, 2007, 17(20), 5620-5623

Production Method 7

92945-21-6

92933-47-6

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Water ;  0 °C; 30 min, 0 °C
1.2 Reagents: Hydrazine sulfate ;  45 min, 0 °C

Reference

Preparation of substituted pyrazolo[4,3-e][1,4]diazepines as phosphodiesterase 4 inhibitors for treatment of obstructive bronchopneumopathy and asthma

, World Intellectual Property Organization, , ,

Production Method 8

78208-72-7

92933-47-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ;  3 h, 50 °C; cooled
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2, cooled

Reference

The discovery of potent, selective, and orally bioavailable PDE9 inhibitors as potential hypoglycemic agents

De Ninno, Michael P.; Andrews, Melissa; Bell, Andrew S.; Chen, Yue; Eller-Zarbo, Cynthia; et al, Bioorganic & Medicinal Chemistry Letters, 2009, 19(9), 2537-2541

Production Method 9

563-80-4

92933-47-6

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: Ethanol
1.2 Reagents: Hydrazine hydrate (1:1)
1.3 Reagents: Sodium hydroxide Solvents: Water

Reference

Agonist lead identification for the high affinity niacin receptor GPR109a

Gharbaoui, Tawfik; Skinner, Philip J.; Shin, Young-Jun; Averbuj, Claudia; Jung, Jae-Kyu; et al, Bioorganic & Medicinal Chemistry Letters, 2007, 17(17), 4914-4919

Production Method 10

78208-72-7

92933-47-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  3 h, rt → 50 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2

Reference

Preparation of pyrazolo[4,3-d]pyrimidin-7-ones as PDE9 inhibitors for treating cardiovascular disorders

, World Intellectual Property Organization, , ,

Production Method 11

78208-72-7

92933-47-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: 1,4-Dioxane ,  Water ;  rt → 50 °C; 3 h, 50 °C; cooled
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2, cooled

Reference

Preparation of pyrazolopyrimidinones as PDE9 inhibitors for treatment of insulin resistance syndrome and type 2 diabetes

, World Intellectual Property Organization, , ,

Production Method 12

78208-72-7

92933-47-6

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol ;  16 h, reflux; cooled
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Preparation of benzimidazoles and analogs and their use as protein kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 13

92933-47-6

Reaction Conditions

Reference

A preparation of pyrrole and pyrazole derivatives, useful as D-amino acid oxidase (Daao) inhibitors

, United States, , ,

Production Method 14

92933-47-6

Reaction Conditions

Reference

Synthesis, antibacterial activity and structure-activity relationships of N-substituted 4-diazopyrazole-5-carboxamides. 2

Baraldi, Pier Giovanni; Cacciari, Barbara; Leoni, Alberto; Recanatini, Maurizio; Roberti, Marinella; et al, Farmaco, 1991, 46(11), 1337-50

5-Isopropyl-1H-pyrazole-3-carboxylic acid Raw materials

• Hexanoic acid, 5-methyl-2,4-dioxo-, ethyl ester, ion(1-), sodium (9CI)
• 3-Methyl-2-butanone
• ethyl 3-(propan-2-yl)-1H-pyrazole-5-carboxylate
• Methyl 5-methyl-2,4-dioxohexanoate

5-Isopropyl-1H-pyrazole-3-carboxylic acid Preparation Products

• 5-Isopropyl-1H-pyrazole-3-carboxylic acid (92933-47-6)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Pyrazole carboxylic acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Pyrazoles Pyrazole carboxylic acids and derivatives

• 83405-71-4(5-tert-butyl-1H-pyrazole-3-carboxylic acid)
• 79445-14-0(5-tridecylpyrazole-3-carboxylic acid)
• 76424-47-0(5-propyl-1H-pyrazole-3-carboxylic acid)
• 890591-72-7(1H-Pyrazole-3-carboxylicacid, 5-cyclopropyl-)
• 92933-49-8(5-(2-methylpropyl)-1H-pyrazole-3-carboxylic acid)
• 4027-59-2(5-Ethyl-1H-pyrazole-3-carboxylic acid)
• 401629-04-7(3-Cyclopropyl-1H-pyrazole-5-carboxylic acid)
• 1101877-35-3(methyl 3-(propan-2-yl)-1H-pyrazole-5-carboxylate)
• 89967-38-4(5-pentyl-1H-pyrazole-3-carboxylic acid)
• 949034-45-1(3-Acetyl-1H-pyrazole-5-carboxylic acid)