Category: 1904-31-0

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, HPLC of Formula: C4H7N3

(E)-Cyclopentyloxyimino-(3,4-dichloro-phenyl)-acetic acid (100 mg, 0.33 mmol) was dissolved in methylene chloride (1.6 mL). N,N-diisopropylethylamine (173 muL, 0.99 mmol) and 1-methyl-1H-pyrazol-3-ylamine (32 muL, 0.33 mmol) were added and the reaction mixture was cooled to 0° C. O-(7-Azabenzotriazole-1-yl)-N,N,N’N’-tetramethyluronium hexafluorophosphate (126 mg, 0.33 mmol) was added and the reaction mixture was allowed to warm to 25° C. After stirring 16 h, the reaction mixture was diluted with chloroform (2 mL) and washed with saturated aqueous sodium bicarbonate solution (1.5 mL). The aqueous phase was extracted with chloroform (1.5 mL) and the combined organic phases were filtered through sodium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (Merck silica gel 60, 40-63 mum; 40percent ethyl acetate/hexanes) to afford (E)-2-cyclopentyloxyimino-2-(3,4-dichloro-phenyl)-N-(1-methyl-1H-pyrazol-3-yl)-acetamide (103 mg, 82percent) as a white solid after lyophilization from aqueous dioxane: LC-MS (ESI) m/e calcd for C17H18Cl2N4O2 [M+] 380.08, found 381 [M+H+]; H1-NMR (400 MHz, CDCl3) .box. ppm 1.64 (m, 4 H, 2*CH2), 1.85 (m, 4 H, 2*CH2), 3.83 (s, 3 H, NCH3), 4.84 (m, 1 H, OCH), 6.70 (d, J=2.3 Hz, 1 H, Ar), 7.26 (d, J=2.3 Hz, 1 H, Ar), 7.33 (dd, Jo=8.3, Jm=1.9 Hz, 1 H, Ar), 7.47 (d, Jo=8.3 Hz, 1 H, Ar), 7.61 (d, Jm=1.9 Hz, 1 H, Ar), 9.15 (s, 1 H, NH).

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; Berthel, Steven Joseph; Kester, Robert Francis; Murphy, Douglas Eric; Prins, Thomas Jay; Ruebsam, Frank; Tran, Chinh Viet; Vourloumis, Dionisios; US2008/146625; (2008); 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., Application In Synthesis of 1-Methyl-1H-pyrazol-3-amine

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

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. 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1904-31-0

1 -Methyl- lH-pyrazo 1-3 -amine (158 mg, 1.63 mmol) and DIEA (1.08 mL, 6.52 mmol) was added to a solution of 2-(l-(ter^-butoxycarbonylamino)cyclobutyl)-2-hydroxyacetic acid (400 mg, 1.63 mmol) dissolved in DMF (20 mL). The solution was cooled to 00C and after 10 minutes HATU (620 mg, 1.63 mmol) was added. After approximately 2 hours at RT, LC-MS showed product and no starting material and the solvent was removed by rotary evaporation. The crude product was dissolved in 40 rnL of EtOAc and washed with 25 rnL of sat. NaHCCh (aq). The organic phase was dried with Na2SO4, filtered and evaporated to dryness. The crude product was purified on a 25 g silica column on a Biotage Flashmaster eluted with a gradient of heptane:ethyl acetate 1 :1, which gave the title compound as a white solid (488 mg, 92percent) yield. [M+H]+ = 325.

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

Reference:
Patent; MEDIVIR UK LTD; AYESA, Susana; BELFRAGE, Anna, Karin; CLASSON, Bjoern; GRABOWSKA, Urszula; HEWITT, Ellen; IVANOV, Vladimir; Joensson, Daniel; KAHNBERG, Pia; LIND, Peter; NILSSON, Magnus; ODEN, Lourdes; PELCMAN, Mikael; WAeHLING, Horst; WO2010/70615; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1904-31-0,Some common heterocyclic compound, 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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.

97 Preparation of N.N-dicyclopropyl-6-ethyl- 1 -methyl -4-( 1 -methyl- 1H- pyrazol-3-ylamino)-1.6-dihydroimidazo[4.5-dlpyrrolo[2.3-blpyridine-7-carboxamide[00465] To a vial containing 1 -methyl- lH-pyrazol-3 -amine (11.89 mg, 0.122 mmol), Pd2(dba)3 (4.67 mg, 5.10 muiotaetaomicron), Xantphos (5.90 mg, 10.20 muiotaetaomicron), and cesium carbonate (100 mg, 0.306 mmol) was added 4-bromo-N,N-dicyclopropyl-6-ethyl-l- methyl-l,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 97A, 41.0 mg, 0.102 mmol) in DME (1020 muKappa). The reaction mixture was sparged with argon for 5 min, the vial was capped, and the reaction mixture was heated at 60 °C for 4 h and 80 °C for 16h. The reaction mixture was concentrated in vacuo. The crude residue was purified by flash column chromatography using an Isco 40 g column eluting with 0 – 5percent MeOH/ (3/4(3/4 followed by additional purification with preparative HPLC. N,N-Dicyclopropyl-6-ethyl-l-methyl-4-(l -methyl- lH-pyrazol-3 – ylamino)-l,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (13 mg, 0.030 mmol, 29.5percent yield) was isolated as a white solid.[00466] MS (ESI) m/z 419.3 (M+H) [00467] 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.17 (s, 1 H), 7.64 (s, 1 H), 7.31 (d, 1H, J= 2.26 Hz), 7.16 (d, 1 H, J= 2.26 Hz), 6.86 (s, 1 H), 4.65 (q, 2 H, J = 7.03 Hz), 4.01 (s, 3 H), 3.85 (s, 3H), 2.78 – 2.87 (m, 2 H), 1.49 (t, 3 H, J= 7.15 Hz), 0.81 – 0.89 (m, 4 H), 0.71 – 0.80 (m, 4 H)

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PURANDARE, Ashok V.; GREBINSKI, James W.; HART, Amy; INGHRIM, Jennifer; SCHROEDER, Gretchen; WAN, Honghe; WO2011/28864; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1904-31-0,Some common heterocyclic compound, 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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.

Example 113; 4-(3,5-Difluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide; To a mixture of 4-(3,5-difluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-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 CH2Cl2 (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, CDCl3): delta 8.82 (s, 1H), 7.20 (m, 2H), 7.03 (d, 2H), 6.73 (s, 1H), 6.42 (m, 3H), 3.72 (s, 3H), 2.84 (s, 2H), 1.42 (s, 6H); LCMS for C21H19F2N3O3 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 Inc.; US2008/280875; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1904-31-0,Some common heterocyclic compound, 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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-Bromo-5-fluoropyridine (1) (1 .Og, 5.71 mmol), i-methyl-i H-pyrazol-3-amine (2) (554mg, 5.7immol), Xantphos (0.330g, 0.S7mmol), and 0s2003 (2.79g, 8.S6mmol) were combined in dry i,4-dioxane (i5mL). The reaction mixture was degassed with N2(g) and placed under vacuum for 10mm. Pd2(dba)3 (0.26ig, 0.28mmol) was then added and the resulting reaction mixture was heated at 9000 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 concentrated in vacuo. The resulting residue was purified by flash chromatographywith EtOAc/Hexane (1:1) to provide 5-fluoro-N-(i -methyl-i H-pyrazol-3-yl)pyridin-2- amine (3) as a yellow solid (0.65g, 6ipercent).LCMS (ES): Found i93.0 [M+H].

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

Reference:
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; TOMASSI, Cyrille Davy; CECIL, Alexander Richard Liam; MACCORMICK, Somhairle; NODES, William John; SILVA, Franck Alexandre; WO2014/181137; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. Formula: C4H7N3

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).

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

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

Reference 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.

To a stirred suspension of 1-methyl-1H-pyrazol-3-amine 76a (0.5 g, 5.1 mmol) in toluene (20 mL) in an round bottom flask fitted with Dean-Stark apparatus was charged with hexane-2,5-dione (0.70 g, 6.1 mmol) followed by p-toluene sulfonic acid (0.097 g, 0.51 mmol) and the reaction mixture was heated at 115°C for about 6 h. The reaction mixture was cooled to room temperature. Reaction mass was concentrated fully under reduced pressure, residue obtained was dissolved in DCM, given water wash followed by brine wash, dried over Na2504 and concentrated under redcued pressure to obtain 3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole 76b (0.55 g, 55percent yield) as green oil. 1HNMR (400 MHz, CDC13): 6 7.39 (d, 111), 6.15 (s, 1H), 5.85 (s, 2H), 3.92 (s, 3H), 2.10 (s, 6H), MS: 176.11 (M+H).

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

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

Application 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.

Example 149:; 4-(4-Dimethylcarbamoyl-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1 -methyl-1 H-pyrazol-3-yl)-amide; To a solution of 4-(4-dimethylcarbamoyl-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofurapi-6-carboxylic acid (149c) (130 mg, 0.366 mmol), 3-amino-1-methyl-pyrazole (71.1 mg, 0.732 mmol) and triethylamine (0.102 ml, 0.732 mmol) in 3 mL of DMF was added HATU (278 mg, 0.732 mmol). The mixture was stirred at 500C for 2 hr, quenched with water, extracted with 3XEtOAc. The combined organic layer was washed with 2XH2O, dried with Na2SO4, concentrated and purified by Biotage column chromatography with 75- 100percent EtOAc in hexanes to give a white solid (134 mg, 84percent yield). 1H NMR (400 MHz, CDCI3) delta 8.69 (s, 1 H) 7.38 – 7.46 (m, 2 H) 7.24 – 7.28 (m, 1 H) 7.01 (d, J=2.78 Hz, 2 H) 6.97 (d, ./=8.59 Hz, 2 H) 6.77 (d, J=2.02 Hz, 1 H) 3.76 (d, 3 H) 3.07 (d, J=22.48 Hz, 6 H) 2.89 (s, 2 H) 1.47 (s, 6 H); LCMS for C24H26N4O4 m/z 435.20 (M+H+); Anal. Calcd. for C24H28N4O4- 0.7 H2O: C, 64.47; H, 6.18; N, 12.53; Found: C, 64.22; H, 6.11; N, 12.54.

Statistics shows that 1-Methyl-1H-pyrazol-3-amine is playing an increasingly important role. we look forward to future research findings about 1904-31-0.

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

Related Products 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.

3,5-Dibromo-1-methyl-1H-pyridin-2-one (469 mg, 1.76 mmol), 1-Methyl-1H-pyrazol-3-ylamine (205 mg, 2.11 mmol), tris(dibenzylidineacetone)dipalladium(0) (80 mg, 0.087 mmol), 2,2′-bis(diphenylphosphino-1,1′-binaphthalene (82 mg, 0.13 mmol), and cesium carbonate (801 mg, 2.46 mmol) were deposited in a sealed vial with 10 mL toluene. This was heated at 130 C. for 18 hours. The resulting mixture was poured into 50 mL water. This was extracted with ethylacetate. The ethylacetate layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (eluted with ethylacete/hexanes) to yield 5-Bromo-1-methyl-3-(1-methyl-1H-pyrazol-3-ylamino)-1H-pyridin-2-one (271 mg, 0.957 mmol). MS (ESI) 284.9 (M+H)+.

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; Berthel, Steven; Firooznia, Fariborz; Fishlock, Daniel; Hong, Jun-Bae; Lou, Yan; Lucas, Matthew; Owens, Timothy D.; Sarma, Keshab; Sweeney, Zachary Kevin; Taygerly, Joshua Paul Gergely; US2010/222325; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics