Production Method 1

92945-27-2

Reaction Conditions

1.1 Reagents: Hydrazine sulfate (1:?) ,  Sodium hydroxide ,  Hydrazine hydrate (1:1) Solvents: Water ;  2 h, pH 7, 60 °C

Reference

Synthesis of 1H-3-n-propyl-pyrazole-5-carboxylic acid ethyl ester

Xu, Bao-cai; Zhou, Zhi-ming; Yu, Hai, Beijing Gongshang Daxue Xuebao, 2002, 20(4), 11-13

Production Method 2

92945-27-2

Reaction Conditions

1.1 Reagents: Sodium methoxide ;  2 °C; 0 °C; 5 °C → 0 °C; 0 °C → 40 °C; 30 min, < 0 °C; 0 °C → 5 °C; 10 min, 5 °C; 5 °C → 40 °C; 30 min, < 0 °C; 0 °C → 5 °C; 10 min, 5 °C; 5 °C → 55 °C; 2 h, 55 °C; 55 °C → 10 °C
1.2 Solvents: Ethyl acetate ;  20 min, 10 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  15 min, pH 1.8 - 2, 10 °C
1.4 Catalysts: p-Toluenesulfonic acid ;  5 °C → 10 °C
1.5 Reagents: Hydrazine hydrate (1:1) ;  1 h, 10 - 25 °C; 45 min, 25 °C; 25 °C → 5 °C
1.6 Reagents: Sodium hydroxide Solvents: Water ;  pH 7.2

Reference

Preparation of pyrazolopyrimidinones for the treatment of impotence

, India, , ,

Production Method 3

36983-31-0

92945-27-2

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Acetic acid ,  2-Methoxyethanol ;  10 min, rt; 3.5 h, 105 °C

Reference

Preparation of deuterated 3-(dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-propoxybenzenesulfonamides as phosphodiesterase PDE5 inhibitors.

, United States, , ,

Production Method 4

36983-31-0

92945-27-2

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Trifluoroacetic acid ,  2-Methoxyethanol ;  overnight, rt → 100 °C

Reference

Preparation of novel polycyclic compounds as dual inhibitors of phosphodiesterases and histone deacetylases

, World Intellectual Property Organization, , ,

Production Method 5

36983-31-0

92945-27-2

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Acetic acid ,  2-Methoxyethanol ;  overnight, rt → 100 °C

Reference

Novel hydroxamic acid compounds as dual inhibitors of phosphodiesterases and histone deacetylases

, World Intellectual Property Organization, , ,

Production Method 6

92945-27-2

Reaction Conditions

1.1 Reagents: Sodium ethoxide Solvents: Ethanol ;  2 h, rt
1.2 Reagents: Acetic acid ,  Hydrazine

Reference

Synthesis of 4-amino-1-methyl-3-n-propylpyrazole-5-carboxamide

Shen, Zhi-qin, Hecheng Huaxue, 2002, 10(3), 257-259

Production Method 7

92945-27-2

Reaction Conditions

1.1 Reagents: Sodium Solvents: Ethanol
1.2 Reagents: Acetic acid ,  Hydrazine ;  8 h, reflux
1.3 Reagents: Sodium bicarbonate Solvents: Water

Reference

Novel process for synthesizing 4-amino-1-methyl-3-propylpyrazolyl-5-formamide

Qin, Shao-qing, Jingxi Yu Zhuanyong Huaxuepin, 2004, 12(5), 12-13

Production Method 8

92945-27-2

Reaction Conditions

1.1 Reagents: Hydrazine Solvents: Acetic acid

Reference

Synthesis of 4-amino-1-methyl-3-propylpyrazole-5-carboxamide

Shen, Jing; You, Cong-Chao; Wu, Song, Zhongguo Yiyao Gongye Zazhi, 2000, 31(9), 419-420

Production Method 9

942040-13-3

92945-27-2

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  45 min, -78 °C; 15 min, 20 °C
1.2 -78 °C; 16 h, -78 °C → 20 °C
1.3 Reagents: p-Toluenesulfonic acid Solvents: Toluene ;  8 h, reflux; reflux → 20 °C
1.4 Reagents: Sodium bicarbonate Solvents: Water ;  15 min, 207 °C

Reference

Synthesis of pyrazole-3-carboxylates and pyrazole-1,5-dicarboxylates by one-pot cyclization of hydrazone dianions with diethyl oxalate

Dang, Tung T.; Dang, Tuan T.; Fischer, Christine; Goerls, Helmar; Langer, Peter, Tetrahedron, 2008, 64(9), 2207-2215

Production Method 10

36983-31-0

92945-27-2

Reaction Conditions

1.1 Reagents: Hydrazine Solvents: Ethanol

Reference

Preparation of N-benzylpyrrole, -pyrazole, and - triazole derivatives as angiotensin II antagonists and as antihypertensives

, European Patent Organization, , ,

Production Method 11

36983-31-0

92945-27-2

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Acetic acid ;  0 °C; 8 h, 0 °C → reflux; cooled

Reference

Pyrazolo[4,3-d]pyrimidine derivative as highly selective and long-acting PDE5 modulators and their preparation

, United States, , ,

Production Method 12

92945-27-2

Reaction Conditions

1.1 Catalysts: Diethylamine Solvents: Dimethyl sulfoxide ;  24 h, rt

Reference

Highly Regioselective Organocatalyzed Synthesis of Pyrazoles from Diazoacetates and Carbonyl Compounds

Wang, Lei; Huang, Jiayao; Gong, Xiaojie; Wang, Jian, Chemistry - A European Journal, 2013, 19(23), 7555-7560

Production Method 13

92945-27-2

Reaction Conditions

1.1 Catalysts: Pyrrolidine Solvents: Dimethyl sulfoxide ;  12 h, rt

Reference

Method for synthesizing 3,4,5-trisubstituted pyrazole-like compound

, China, , ,

Production Method 14

36983-31-0

92945-27-2

Reaction Conditions

1.1 Reagents: Acetic acid ,  Hydrazine hydrate (1:1) Solvents: 2-Methoxyethanol ;  10 min, rt; 3.5 h, 105 °C

Reference

3-(Dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-propoxybenzenesulfonamide derivatives as phosphodiesterase inhibitors

, United States, , ,

Production Method 15

92945-27-2

Reaction Conditions

1.1 Reagents: Sodium ethoxide ;  2.5 h, rt; rt → 60 °C; 1 h, 60 °C
1.2 Reagents: Acetic acid ,  Hydrazine

Reference

Synthesis of 1-methyl-3-n-propylpyrazole-5-carboxylic acid

Shen, Zhiqin, Huaxue Shijie, 2002, 43(4), 208-210

Production Method 16

92945-27-2

Reaction Conditions

1.1 Reagents: Sodium Solvents: Ethanol
1.2 Reagents: Hydrazine hydrate (1:1) Solvents: Acetic acid

Reference

Improved process for the synthesis of 1-methyl-4-nitro-3-propylpyrazole-5-carboxamide

Huang, Haihong; Zhang, Xiang; Zhang, Manyun; Huang, Daofei, Zhongguo Yiyao Gongye Zazhi, 2001, 32(7), 319-320

Production Method 17

36983-31-0

92945-27-2

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Acetic acid ;  8 h, 0 °C → reflux

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 18

92945-27-2

Reaction Conditions

1.1 Reagents: Acetic acid ,  Hydrazine hydrate (1:1)
1.2 Reagents: Sodium carbonate

Reference

Process for synthesizing ethyl 5-propylpyrazole-3-carboxylate

, China, , ,

Production Method 19

942040-13-3

92945-27-2

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  45 min, -78 °C; 15 min, 20 °C
1.2 -78 °C; 16 h, -78 °C → 20 °C
1.3 Reagents: p-Toluenesulfonic acid Solvents: Toluene ;  8 h, reflux; reflux → 20 °C
1.4 Reagents: Sodium bicarbonate Solvents: Water ;  15 min, 20 °C

Reference

One-pot synthesis of pyrazole-5-carboxylates by cyclization of hydrazone 1,4-dianions with diethyl oxalate

Dang, Tuan Thanh; Dang, Tung Thanh; Langer, Peter, Tetrahedron Letters, 2007, 48(20), 3591-3593

Ethyl 5-Propyl-1H-pyrazole-3-carboxylate Raw materials

• Hydrazinecarboxylic acid, 2-(1-methylbutylidene)-, ethyl ester
• 2,4-Dioxoheptanoic Acid Ethyl Ester

Ethyl 5-Propyl-1H-pyrazole-3-carboxylate Preparation Products

• Ethyl 5-Propyl-1H-pyrazole-3-carboxylate (92945-27-2)

• 1. Excimer–monomer switch: a reaction-based approach for selective detection of fluoride?
  Qiao Song,Angela Bamesberger,Lingyun Yang,Haley Houtwed,Haishi Cao Analyst, 2014,139, 3588-3592
• 2. Enantiomerically pure 1,3,2-dioxaborolanes: new reagents for the hydroboration of alkynes
  Chem. Commun., 1998, 2651-2652
• 3. Fc microparticles can modulate the physical extent and magnitude of complement activity?
  David White,Sean R. Stowell Biomater. Sci., 2017,5, 463-474
• 4. Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors?
  Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon Cho J. Mater. Chem. C, 2020,8, 1686-1696
• 5. Excellent energy storage performance in NaNbO3-based relaxor antiferroeic ceramics under a low electric field
  XuxinCheng,XiaomingChen,PengyuanFan

• Solvents and Organic Chemicals Organic Compounds Acids/Esters

• 834869-10-2(3-Ethyl-5-pyrazolcarboxylic acid methyl ester)
• 78208-72-7(ethyl 3-(propan-2-yl)-1H-pyrazole-5-carboxylate)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 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)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)