Category: 175137-46-9

Electric Literature of 175137-46-9, A common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, molecular formula is C6H9N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 2,3,6-trichloro-5-nitropyridine (1.62 g, 7.10 mmol) and DIEA (1.24 ml, 7.1 mmol) in THF (25 ml) was added dropwise a solution of 5-cyclopropyl-lH-pyrazol-3- amine (0.70 g, 5.68 mmol) in THF (5 ml) at 0 C. After addition, the reaction mixture was stirred at 25 C for 24 hours. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : EtOAc = 1.5 : 1) to give the title compound as a yellow solid (0.83 g, 47%). NMR (400 MHz) 12.39 (s, IH), 10.12 (s, IH), 8.77 (d, J= 1.2 Hz, IH), 6.35 (s, IH), 1.95 (m, IH), 0.96 (m, 2H), 0.71 (m, 2H). MS: Calcd.: 313; Found: [M+H]+ 314

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/82392; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 175137-46-9, These common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 2,4-difluoro-5-nitrobenzonitrile (Method 9, 5.0 g, 27 mmol) and DIEA (5.4 ml, 31 mmol) in THF (20 ml) was added dropwise the solution of 5-cyclopropyl- 1H-pyrazol-3-amine (3.2 g, 26 mmol) in THF (5 ml) at 0 C. After addition, the reaction mixture was stirred at 25 C for 1 hr. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : EtOAc = 3 : 1) to give the title compound as a yellow solid (5.5 g, 74%). NMR (400 MHz) 12.54 (s, 1H), 10.13 (s, 1H), 8.78 (d, J= 7.2 Hz, 1H), 8.10 (d, J= 13.6 Hz, 1H), 6.02 (s, 1H), 1.91 (m, 1H), 0.97 (m, 2H), 0.72 (m, 2H). MS: Calcd. : 287; Found: [M+H]+ 288.

Statistics shows that 5-Cyclopropyl-1H-pyrazol-3-amine is playing an increasingly important role. we look forward to future research findings about 175137-46-9.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/103010; (2005); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 175137-46-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 175137-46-9 name is 5-Cyclopropyl-1H-pyrazol-3-amine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 1,2,3-trifluoro-4-nitrobenzene (3.2 g, 18 mmol) and DIEA (4.2 ml, 24 mmol) in dry THF (20 ml) was added dropwise the solution of 5-cyclopropyl-lH-pyrazol-3- amine (2.0 g, 16 mmol) in THF (5 ml) at 0 C. After addition, the reaction mixture was stirred at 25 C for 21 hrs. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : EtOAc = 5. : 2). Recrystallization from EtOAc (10 ml) and hexanes ((at)100 ml) gave the title compound as red crystals (1.5 g, 33%). NMR (400 MHz) 11.90 (s, 1H), 8.78 (s, 1H), 7.86 (t, J= 7.6 Hz, 1H), 7.08 (q, J= 8.7 Hz, 1H), 5.60 (s, 1H), 1.83 (m, 1H), 0.89 (m, 2 H), 0.65 (m, 2H). MS: Calcd. : 280; Found: [M+H]+ 281.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Cyclopropyl-1H-pyrazol-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/103010; (2005); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 175137-46-9,Some common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, molecular formula is C6H9N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

21F. 2-((4-(5-Cyclopropyl-lH-pyrazol-3-ylamino)pyrrolo [1,2-f][l,2,4]triazin-2- yl)methyl)isoindoline-l,3-dione. 2-((4-Chloropyrrolo[l,2-/|[l,2,4]triazin-2-yl)methyl)isoindoline-l,3-dione (4.43 g, 14.17 mmol) was suspended in NMP (50 mL), then DIPEA (4.95 mL, 28.3 mmol) was added. The mixture was heated to 80 0C, to which was slowly added via syringe a solution of S-cyclopropyl-lH-pyrazol-S-amine (3.49 g, 28.3 mmol) in NMP (20 mL). The reaction was stirred at 80 0C for 2 h, then cooled to room temperature. The reaction was diluted with EtOAc (700 mL) and washed with water (3 x 500 mL) and brine (2 x 250 mL). The organics were dried (MgSO4), filtered, and concentrated in vacuo. The residue was dissolved in a minimum of EtOAc and diluted with hexanes, and the precipitate was filtered and dried. The solids were triturated twice with 20% EtOAc/Hex, once with 20% DCM/Hex, and finally in 50% DCM/Hex to give 21F (3.35 g, 59%). 21F had an analytical HPLC retention time = 3.368 min (Phenomonex-Luna (4.6 x 50 mm SlO); 10-90% MeOH/H2O (0.1% TFA) over 4 min; flow = 4 mL/min) and a LC/MS M+ +1 = 400.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Cyclopropyl-1H-pyrazol-3-amine, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/131050; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 175137-46-9,Some common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, molecular formula is C6H9N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 2,5,6-trichloronicotinonitrile (Method 44, 1.0 g, 4.8 mmol) and DIEA (0.81 g, 6.2 mmol) in n-BuOH (5 ml) was added S-cyclopropyl-lH-pyrazol-S-amme (2.3 g, 19.3 mmol). The reaction was heated to 60 0C for 2 hours, at which point the reaction was cooled to room temperature and concentrated. The resulting residue was diluted with 10 ml ACN, and stored at 00C for 1 hour. The solids that formed were then filtered, washed with cold ACN, dried and collected to give the title compound (0.62 g, 43%). MS: Calcd.: 294; Found: [M+H]+ 295.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Cyclopropyl-1H-pyrazol-3-amine, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/82392; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 175137-46-9,Some common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, molecular formula is C6H9N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A solution of 5-cyclopropyl-1H-pyrazol-3-amine (0.267 g, 2.17 mmol) and 2,4,6-trichloroquinazoline (0.432 g, 2.17 mmol) in dimethylformamide (DMF) (10 mL) was treated with EtN(i-Pr)2 (0.49 mL, 2.82 mmol) and stirred for 4 h at 0 C. The reaction mixture was poured over ice water. The solid was collected by filtration and dried in air to provide compound 5 without further purification [16]. The yield was 74.6%.

The synthetic route of 175137-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Tianxiao; Pang, Yu; Guo, Jing; Yin, Wenbo; Zhu, Mingyue; Hao, Chenzhou; Wang, Kai; Wang, Jian; Zhao, Dongmei; Cheng, Maosheng; Molecules; vol. 23; 2; (2018);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Cyclopropyl-1H-pyrazol-3-amine

101B. 2-Chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrrolo[1,2-f][1,2,4]triazine-7-carbaldehyde A mixture of 101A (371 mg, 1.72 mmole), 5-cyclopropyl-1H-pyrazol-3-amine (139 mg, 1 equiv), and diisopropylethylamine (0.51 mL, 1.7 equiv) in isopropyl alcohol (1.7 mL) was stirred at RT overnight. The reaction was diluted with a mixture of dichloromethane_methanol=9:1, washed with water and dried (Na2SO4). Removal of the solvents followed by radial silica gel chromatography (step gradient elution with mixtures of dichloromethane containing 0 to 7.5% methanol) afforded the product as a solid (279 mg, 54% yield): MS: 303 (M+H)+; HPLC Ret Time: 2.61 min (Phenomenex-Luna S10 3.0*50 mm column, 3 min gradient, 4 mL/min).

The synthetic route of 175137-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/9497; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 175137-46-9, These common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Intermediate 15 2,5-dichloro-N-(5-cvclopropyl-lH-pyrazol-3-yl)pyrimidin-4-amine [0096] A mixture of 5-cyclopropyl-lH-pyrazol-3-amine (246 mg, 2.00 mmol), 2,4,5-trichloropyrimidine (367 mg, 2.00 mmol, 1 equiv.) and Na2CO3 (233 mg, 2.20 mmol, 1.1 equiv.) in EtOH (10 mL) was heated at 40 0C for 16 h. The crude reaction mixture was diluted with EtOAc and sequentially washed with: water (3x) and saturated aqueous NaCl (Ix). The resulting EtOAc layer was dried over Na2SO4 and then concentrated in vacuo, providing 2,5-dichloro-N-(5-cyclopropyl-lH-pyrazol-3- yl)pyrimidin-4-amine; ESMS m/z 270.0 (M + H+).

The synthetic route of 175137-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2009/158431; (2009); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 175137-46-9

5,6-Chloro-iV-(5-cvclopropyl-l//-pyrazol-3-yl)-3-nitropyridine-2-amine To a solution of 2,3,6-trichloro-5-nitropyridine (1.62 g, 7.10 mmol) and DIEA (1.24 ml, 7.1 mmol) in THF (25 ml) was added dropwise a solution of 5-cyclopropyl-lH”-pyrazol-3- amine (0.70 g, 5.68 mmol) in THF (5 ml) at 0 0C. After addition, the reaction mixture was stirred at 25 0C for 24 hours. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : EtOAc = 1.5 : 1) to give the title compound as a yellow solid (0.83 g, 47%). NMR (400 MHz) 12.39 (s, IH), 10.12 (s, IH), 8.77 (d, J= 1.2 Hz, IH), 6.35 (s, IH), 1.95 (m, IH), 0.96 (m, 2H), 0.71 (m, 2H). MS: Calcd.: 313; Found: [M+H]+ 314.

The synthetic route of 5-Cyclopropyl-1H-pyrazol-3-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/87530; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 175137-46-9, These common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of2,4-difluoro-l-nitrobenzene (1.76 g, 11.1 mmol) and DIEA (1.93 ml, 11.1 mmol) in THF (20 ml) was added dropwise the solution of 5-cyclopropyl-1H-pyrazol-3- amine (0.91 g, 7.39 mmol) in THF (5 ml) at 25 C. After addition, the reaction mixture was stirred at 80 C for 48 hrs. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : DCM : EtOAc = 2 : 1 : 1) to give the title compound as a yellow solid (0.62 g, 32%). NMR (400 MHz) 12.37 (s, 1H), 9.83 (s, 1H), 8.25 (m, 1H), 7.98 (d, J= 11.2 Hz, 1H), 6.75 (m, 1H), 5.95 (s, 1H), 1.90 (m, 1H), 0.96 (m, 2H), 0.72 (m, 2H).

Statistics shows that 5-Cyclopropyl-1H-pyrazol-3-amine is playing an increasingly important role. we look forward to future research findings about 175137-46-9.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/103010; (2005); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics