Category: 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. Recommanded Product: 175137-46-9

The solution of 1,3,5-trifluoro-2-nitrobenzene (6.50 g, 37 mmol), 5-cyclopropyl-1H- pyrazol-3-amine (3.50 g, 28 mmol) and DIEA (6.4 ml, 37 mmol) in THF (100 ml) was stirred at 25 C for 80 hours. The solvent was removed under reduced pressure and the residue was purified by chromatography (DCM-EtOAc = 10 : 1) to give the title compound as yellow solid (4.9 g, 62%). NMR (400 MHz) 12.26 (s, 1H), 9.09 (s, 1H), 7.70 (d, J= 12.8 Hz, 1H), 6.88 (m, 1H), 5.80 (s, 1H), 1.88 (m, 1H), 0.93 (m, 2H), 0.69 (m, 2H).

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; WO2005/103010; (2005); A2;,
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.

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.

2,4-dichloropyrimidine 2 (13.30 g, 89.31 mmol) and 3-amino-5-cyclopropylpyrazole 1 (11.00 g, 89.31 mmol) were dissolved in tetrahydrofuran (TFA) (100 ml) followed by theaddition of deionized water (100 ml). The solution was then treated with potassium acetate (261.9 g, 2.5 mol). The resulting mixture was kept at 55C for 48 h. The mixture was filtered to remove excess potassium acetate. The organic layer was separated and dried using magnesium sulfate and concentrated before loading on an AnaLogix silica column. Intermediate 3 was separated as previously reported (34). ?H NMR (400 MHz, DMSO) oe 12.14 (s, 1H), 10.23 (s,1H), 1.84 (m, 1H), 0.88 (m, 2H), 0.64 (m, 2H). ?3C NMR (100 MHz, DMSO) oe 161.4, 160.7,160.0, 153.9, 148.6, 147.8, 146.8, 8.4, 8.2. MS calculated for C,0H,0N5 235.06, found 236.15 (M).

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; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; SHOKAT, Kevan, M.; MENDEZ, Aaron, S.; (131 pag.)WO2016/22839; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products 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 2,4,6-trichloropyrimidine (Alfa, 12.25 g, 66.8 mmol), 3-amino-5- cyclopropyl-lH-pyrazole (Fluorochem 8.23 g, 66.8 mmol) and triethylamine (11.2 mL, 80.4 mmol) in ethanol (100 mL) was stirred at room temperature for 16 hours under Ar (balloon). The solvent was removed in vacuo and the crude material was dissolved in ethyl acetate. The solution was washed with water and dried (Na2S04), filtered and evaporated to give a beige solid. Pure product was obtained as a white crystalline solid afterrecrystallisation from acetonitrile. It was possible to obtain a second crop. From two runs performed under the same conditions, 29.0 g (88%) of 2,6-dichloro-N-(5-cyclopropyl-lH- pyrazol-3-yl)pyrimidin-4-amine. The product contained -10 % acetonitrile but was carried through to the next step regardless.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BANDYOPADHYAY, Deepak; EIDAM, Patrick M.; GOUGH, Peter J.; HARRIS, Philip Anthony; JEONG, Jae U.; KANG, Jianxing; KING, Bryan Wayne; LAKDAWALA SHAH, Ami; MARQUIS, JR., Robert W.; LEISTER, Lara Kathryn; RAHMAN, Attiq; RAMANJULU, Joshi M.; SEHON, Clark A; SINGHAUS, JR., Robert; ZHANG, Daohua; WO2014/125444; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H9N3

Referential Example 5 2-Chloro-N-(5-cyclopropyl-lH-pyrazol-3-yl)-6-methylpyrimidin-4-amine (189) A mixture of 5-cyclopropyl-lH-pyrazol-3 -amine (1.98 g, 16.07 mmol), 2,4-dichloro-6-methyl-pyrimidine (2.62 g, 16.07 mmol), DIPEA (5.7 mL, 32.15 mmol) and anhydrous EtOH (50 mL) was stirred at 70 oC under N2 for 3 d. The reaction mixture was cooled and poured into water (ca. 700 mL). The reaction was stirred at RT overnight until solid precipitated out. The solid was filtered, washed with additional water and pumped dry under high- vacuum to afford 2.37 g (59%) of 189 as a solid: 1H NMR (400 MHz, DMSO-i/6) delta 12.12 (s, 1H), 10.08 (s, 1H), 7.04 (br s, 1H), 5.93 (br s, 1H), 2.27 (s, 3H), 1.93 to 1.84 (m, 1H), 0.96 – 0.88 (m, 2H), 0.70 – 0.64 (m, 2H).

According to the analysis of related databases, 175137-46-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WO2013/26914; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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

Electric Literature 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

Synthetic Route 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

Reference 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 l,2,3,4-tetrafluoro-5-nitrobenzene (3.0 g, 15.4 mmol) and DIEA (3.7 ml, 21.0 mmol) in dry THF (20 ml) was added S-cyclopropyl-l/f-pyrazol-S-amine (1.7 g, 14.0 mmol) in THF (5 ml) drop wise at 0 C. After addition, the reaction mixture was stirred at 25 C for 16 hours. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane-EtOAc = 4 : 1). This was recrystalized from Et2O (20ml) and hexanes (~150ml) to give the title compound as red crystals (0.650 g, 16%). 1H NMR (400 MHz) 11.84 (s, IH), 8.67 (s, IH), 8.06 (m, IH), 5.57 (s, IH), 1.82 (m, IH), 0.89 (m, 2H), 0.65 (m, 2H). MS: Calcd.: 298; Found: [M+H]+ 299.

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; WO2006/87530; (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.

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