Category: 1904-31-0

1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C4H7N3

Synthesis Example 4 Synthesis of ethyl 3-chloro-1-methyl-5-pyrazolecarboxylate (Compound No. 4.3 (a) of the invention) 6.5 g of 3-amino-1-methylpyrazole was dissolved in 55 ml of conc. hydrochloric acid. To this solution was added dropwise a solution of 6.22 g of sodium nitrite in 12.5 ml of water while maintaining the temperature of from 0° to 5° C. through cooling with ice. After the completion of the dropwise addition, the stirring was continued at this temperature for 1 hour. The above-mentioned diazonium solution was added dropwise to a suspension of 7 g of cuprous chloride in 55 ml of chloroform. 2 g of cuprous chloride were twice added thereto during that time. After the completion of the dropwise addition, the mixture was reacted at 50° C. for 5 hours, and was then stirred at room temperature for 15 hours. This solution was filtered using a Celite, and was then neutralized with a sodium carbonate aqueous solution. The chloroform layer was extracted, and the aqueous layer was further extracted twice with 50 ml of chloroform. The combined chloroform solution was washed with a saturated aqueous solution of sodium chloride, and was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 7 g of a crude product. This crude product was purified through silica-gel column chromatography to obtain 5.2 g of 3-chloro-1-methylpyrazole as a yellow oil.

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nissan Chemical Industries, Ltd.; US5817829; (1998); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1904-31-0, name is 1-Methyl-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. Quality Control of 1-Methyl-1H-pyrazol-3-amine

Step 1: (S) -tert-Butyl (1- (2- (3- (cyclopropylmethoxy) -4- (difluoromethoxy) phenyl) -4- ( (1-methyl-1H-pyrazol-3-yl) carbamoyl) oxazol-5-yl) ethyl) carbamate[2043]To 15 mL of dichloromethane were added (S) -5- (1- ( (tert-butoxycarbonyl) amino) ethyl) -2- (3- (cyclopropylmethoxy) -4- (difluoromethoxy) phenyl) oxazole-4-carboxylic acid (250 mg, 0.53 mmol) , 3-amino-1-methylpyrazole (62 mg, 0.64 mmol) , 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (153 mg, 0.80 mmol) and 1-hydroxy-7-azabenzotriazole (182 mg, 1.33 mmol) . To the mixture was added N, N-diisopropylethylamine (0.37 mL, 2.14 mmol) dropwise at 0 . The resulting mixture was stirred at rt for 3.5 hours. The reaction mixture was washed with water (10 mL × 2) and the organic layer was dried over anhydrous sodium sulfate. The organic solvent was removed and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) 2/1) to give a white solid (260 mg, 85) .[2044]1H NMR (400 MHz, CDCl3) : delta ppm 7.59 (s, 1H) , 7.58 ?7.55 (m, 1H) , 7.31 (d, J 2.1 Hz, 1H) , 7.25 (d, J 8.8 Hz, 1H) , 6.79 (d, J 2.2 Hz, 1H) , 6.71 (t, JF-H 75.1 Hz, 1H) , 5.36 ?5.32 (m, 1H) , 4.00 (d, J 7.0 Hz, 2H) , 3.86 (s, 3H) , 1.56 (d, J 7.0 Hz, 3H) , 1.43 (s, 9H) , 1.37 ?1.32 (m, 1H) , 0.73 ?0.68 (m, 2H) , 0.46 ?0.42 (m, 2H) and MS-ESI: m/z 548.8 [M+H]+.

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

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Bing; YU, Tianzhu; ZHANG, Yingjun; ZHANG, Xiangyu; ZHANG, Shiguo; CHENG, Changchung; ZHANG, Jiancun; WO2015/161830; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1904-31-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1904-31-0 as follows.

To a suspension of 6-((6-bromo-1 H-[1 ,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (68 mg, 0.2 mmol) (prepared from quinolin-6-ylmethanamine following the procedures of Compound 1 ) and 1-methyl-1 H-pyrazol-3-amine (20 mg, 0.22 mmol) in dioxane (5ml_) were added Cs2C03 (72 mg, 0.22 mmol) and H20 (0.5 ml_). The mixture was degassed and charged with N2 three times, then Pd2(dba)3 (0.02 mmol, 18 mg) and xantphos (0.04 mmol, 23 mg) were added. The resulting mixture was stirred at 120°C under one atmosphere of N2 overnight, then concentrated. The resulting residue was purified by chromatography to afford the title compound (10 mg). MS (m/z): 358 (M-M f.

According to the analysis of related databases, 1904-31-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; JIA, Hong; DAI, Guangxiu; WO2011/79804; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1904-31-0, Safety of 1-Methyl-1H-pyrazol-3-amine

To a mixture of 27 (160 mg, 0.45 mmol), 1-methyl-1H-pyrazol-3-amine (48 mg, 0.49 mmol), Pd2(dba)3 (38 mg, 0.024 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 27 mg, 0.047 mmol) in toluene (5 mL) was added Cs2CO3(220 mg, 0.68 mmol), and the mixture was stirred at 85 °C for 2 h under an argon gas atmosphere. After cooling at room temperature, the mixture was concentrated in vacuo. The residue was purifiedby silica gel column chromatography (0?30percent EtOAc in CHCl3) to give 30b (145 mg, 87percent) as an orange solid. 1H NMR (CDCl3) delta 3.78 (s, 3H), 5.41 (s, 2H), 5.91 (d, 1H, J = 2.2 Hz), 6.51 (dd, 1H, J = 9.5, 2.7 Hz), 7.21 (d, 1H, J = 2.2 Hz), 7.48 (d, 1H, J = 2.6 Hz), 7.54?7.59 (m, 1H), 7.62 (d, 1H, J = 8.5 Hz), 7.73?7.78 (m, 1H), 7.83?7.86 (m, 1H), 8.06 (d, 1H, J = 8.6 Hz), 8.18?8.23 (m, 2H), 10.02 (s, 1H); MS (ESI) m/z 376 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Hamaguchi, Wataru; Masuda, Naoyuki; Isomura, Mai; Miyamoto, Satoshi; Kikuchi, Shigetoshi; Amano, Yasushi; Honbou, Kazuya; Mihara, Takuma; Watanabe, Toshihiro; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7612 – 7623;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1904-31-0, The chemical industry reduces the impact on the environment during synthesis 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, I believe this compound will play a more active role in future production and life.

To a stirred solution of 1-methyl-1H-pyrazol-3-amine 58 (5.0 g, 51.50 mmol) in Conc.HC1 (40 mL) at 0°C, sodium nitrite (5.30 g, 77 mmol) in water was added at 0°C and the mixture was stirred at RT for 30 mm. Copper (I) chloride was dissolved in concentrated hydrochloric acid (10 mL) and added to the above mixture drop-wise. The reaction was heated at 60°C, catalytic amount of Cu(I)Cl was added at 60°C (initiating the evolution of gas). Reaction mixture was stirred at 60°C for 30 mm. The mixture was then poured to chilled 50percent NaOH solution & stirred properly; aqueous was extracted with DCM. The organic layer was washed with brine solution, dried over anhydrous sodium sulfate, filtered and solvents evaporated to obtain a crude product (5.50 g, quantitative yield). 1HNMR (400 MHz, CDC13): oe 7.27 (d, 1H), 6.15 (d, 1H), 3.85 (s, 3H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Methyl-1H-pyrazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; SIVANANDHAN, Dhanalakshmi; BAKTHAVATCHALAM, Rajagopal; KETHIRI, Raghava Reddy; VISWANADHAN, Vellarkad Narayana; GIRI, Sanjeev; WO2015/25197; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1904-31-0, These common heterocyclic compound, 1904-31-0, name is 1-Methyl-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.

2-Bromopyridine (1) (1 .Og, 6.3mmol), 1-methyl-I H-pyrazol-3-amine (2) (0.79g,8.2mmol), Xantphos (0.37g, 0.63mmol), and Cs2003 (4.Ig, 12.6mmol) were combined in dry 1,4-dioxane (I5mL). The reaction mixture was then degassed with N2(g), and placed under vacuum for 10mm. Pd2(dba)3 (0.29g, 0.3Immol) was added and the resulting reaction mixture was heated at 90°C for 30h. It wasthen poured onto demineralized water (200mL), and extracted with EtOAc (3 x100mL). The organic phases were combined, dried over Na2SO4, filtered and subsequently evaporated under vacuum. The resulting residue was purified by flash chromatography, eluting with EtOAc/Hexane (1:1) to provide N-(1-methyl- I H-pyrazol-3-yl)pyridin-2-amine (3) as a yellow solid (0.75g, 68percent).LCMS (ES): Found 175.2 [MH].

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; TOMASSI, Cyrille Davy; CECIL, Alexander Richard Liam; MACCORMICK, Somhairle; NODES, William John; SILVA, Franck Alexandre; WO2014/72714; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1904-31-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1904-31-0 as follows.

Example 290a 5-Bromo-1-methyl-3-(1-methyl-1H-pyrazol-3-ylamino)pyridin-2(1H)-one 290a A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (100 mL), 1-methyl-1H-pyrazol-3-amine (970 mg, 10.0 mmol), 3,5-dibromo-1-methylpyridin-2-(1H)-one (2.9 g, 11 mmol), and cesium carbonate (6.5 g, 20.0 mmol). After bubbling nitrogen through the suspension for 10 minutes, tris(dibenzylideneacetone)dipalladium(0) (457 mg, 0.50 mmol) and Xantphos (587 mg, 1.0 mmol) were added. The system was subjected to three cycles of vacuum/argon flush and heated at reflux for 2 h. It was then cooled to room temperature and filtered. The solid was washed with dichloromethane (2 X 50 mL) and the combined organic filtrate was concentrated. The residue was purified by silica-gel column chromatography eluting with 30:1 dichloromethane/methanol to afford 290a as a yellow solid (900 mg, 32%). MS-ESI: [M+H]+ 283.1

According to the analysis of related databases, 1904-31-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
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. 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Methyl-1H-pyrazol-3-amine

General procedure: Amino-pyr azole 1 (0.291 g, 0.003 mol) and an aqueous solution of NaBr (100 mL) (concentrations were as follows: 1 in entries 1 and 2, 2 Min entries 3 and 5-9, and 3 in entry 4) were placed in a cell. In experiment 2, NaHCO3 (0.504 g, 0.006 mol) was added to the solution. The electrolysis was carried out at the following currents: 426 mA for entries 1-4, 213 mA for entry 5, 710 mA for entries 6, 8, and 9, and 852 mA for entry 7. In experiment 9, 48% aqueous solution of HBr was periodically added to the reaction mixture to maintain 7. After passing 2 F of electricity per 1 mole of the starting aminopyrazole 1(Q= 579 C) for entries 1-7or 8 F (Q= 2316 C) for entries 8and 9, the electrolysis was stopped, the reaction mixture was stirred for 1 h and analyzed by TLC (eluent light petroleum ether-ethyl acetate (1 : 1)). Then, the mixture obtained was diluted with concentrated HCl (to 3) and the products were extracted with CHCl3 (3×30 mL). The extracts were combined, dried with anhydrous MgSO4, and concentrated in vacuo. The products were isolated using column chromatography on SiO2 (eluent light petroleum ether-ethyl acetate). The following compounds were isolated: 1,2-bis(1-methyl-1H-pyrazol-3-yl)-diazene (7) (entries 1-7; the product was identified by m.p. 201-202 C (cf. Refs 2 and 4: m.p. 201 C) and the reported 2,41 NMR spectra) and 1,2-bis(4-bromo-1-methyl-1H-pyrazol-3-yl)diazene (8) (entries 8 and 9, the product was identified by NMR spectroscopy and high resolution mass spectrometry). The aqueous layer obtained after extraction was concentrated in vacuo, diluted with NaOH with stirring (to 10), and treated as described above. This resulted in the isolation of 3-amino-4-bromo-1-methyl-1H-pyrazole (6) (entries 1-9; the product was identifi ed by m.p. 97 C (cf. Ref. 10: m.p. 97-98 C) and the reported 51 NMR spectra) and unreacted aminopyr-azole 1(entries 1-8; the starting compound was identified by TLC and NMR spectroscopy). 1,2-Bis(4-bromo-1-methyl-1H-pyrazol-3-yl)diazene (8).Yellow crystals. M.p. 211-213 C. Rf 0.13 (eluent light petroleum ether-ethyl acetate (1:5)). 1H NMR, :4.02 (s, 6 H, Me); 7.50 (s, 2 H, CH). 13C NMR, :40.4 (2 Me), 90.1 (2 CBr), 132.9 (2 CH), 157.5 (2 CN). Found: m/z 348.9217 [M + H]+. C8H979Br2N6. Calculated: [M + H]+= 348.9230

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1904-31-0.

Reference:
Article; Lyalin; Sigacheva; Kokorekin; Dutova, T. Ya.; Rodionov; Petrosyan; Russian Chemical Bulletin; vol. 67; 3; (2018); p. 510 – 516; Izv. Akad. Nauk, Ser. Khim.; 3; (2018); p. 510 – 516,7;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., Recommanded Product: 1904-31-0

Example 113:; 4-(3,5-Difluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1- methyl-1 H-pyrazol-3-yl)-amide; To a mixture of 4-(3,5-difluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofurapi-6-carboxylic acid (113b) (0.308 g, 0.00096 mol), EDCI (0.28 g, 0.0015 mol), HOBt (0.21 g, 0.0015 mol) and NMM (0.49 g, 0.0048 mol) in CH2CI2 (15 mL) was added 1-methyl-1H-pyrazol-3-amine (0.11 g, 0.001 mol) in one portion. The mixture was stirred at room temperature overnight. The reaction mixture was washed with water, aq. citric acid and then sat. NaHCO3. The organic phase was dried over Na2SO4 and concentrated to give a brown oil. The crude oil was purified by prep. HPLC to give the title compound (95 mg, 51percent yield) as a white solid. 1H NMR (400 MHz, CDCI3): delta 8.82 (s, 1H)1 7.20 (m, 2H), 7.03 (d, 2H), 6.73 (s, 1H), 6.42 (m, 3H), 3.72 (s, 3H)1 2.84 (s, 2H), 1.42 (s, 6H); LCMS for C2IH19F2N3O3 m/z 400.4 (M+H)+.

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/122482; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Methyl-1H-pyrazol-3-amine

2-Bromo-5-fluoropyridine (1) (1 .Og, 5.71 mmcl), 1-methyl-I H-pyrazol-3-amine (2) (554mg, 5.7Immol), Xantphos (0.33g, 0.57mmol), and Cs2003 (2.79g, 8.56mmol) were combined in dry 1,4-dioxane (I5mL). The reaction mixture was degassed with N2(g) and placed under vacuum for 10mm. Pd2(dba)3 (0.26g,0.28mmol) was then added and the resulting reaction mixture was heated at90°C for 30h. It was then poured onto demineralized water (200mL), and extracted with EtOAc (3 x IOOmL). The organic phases were combined, dried over Na2SO4, filtered and subsequently evaporated under vacuum. The resulting residue was purified by flash chromatography, eluting with EtOAc/Hexane (1:1)to provide 5-fluoro-N-(1-methyl-IH-pyrazol-3-yl)pyridin-2-amine (3) as a yellow solid (0.65g, 61percent).LCMS (ES): Found 193.0 [MH]+.

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; TOMASSI, Cyrille Davy; CECIL, Alexander Richard Liam; MACCORMICK, Somhairle; NODES, William John; SILVA, Franck Alexandre; WO2014/72714; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics