Category: 578008-32-9

These common heterocyclic compound, 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, 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: 578008-32-9

Intermediate 90(S)-4-(3-((tert-Butyldimethylsilyloxy)methyl)morpholino)-6-(l-(3,5-difluoropyridin-2-vD-2- methoxyethoxy)-5-fluoro-N-(5-methyl-lH-pyrazol-3-yl)pyrimidin-2-amine (3,S<)-3-({[fert-Butyl(dimethyl)silyl]oxy}methyl)-4-{2-chloro-6-[l-(3,5-difluoropyridin-2-yl)-2- methoxyethoxy]-5-fluoropyrimidin-4-yl}morpholine (Intermediate 62), tert-butyl 3-amino-5- methyl-lH-pyrazole-1-carboxylate (Intermediate 10), BINAP, Pd2(dba)3, and CS2CO3 in dioxane (2 ml) was heated at 950C for 8h. LCMS indicated complete reaction. Methanol (1 ml) was added and the reaction was stirred at r.t for Ih. Solvent was removed under reduced pressure and the reaction mixture was purified by ISCO column. The material obtained was directly used in the subsequent step without further purification. LCMS: 610[M+eta]+. The synthetic route of tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate has been constantly updated, and we look forward to future research findings. Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/132502; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 578008-32-9, These common heterocyclic compound, 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, 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.

The product of the previous step (6.6 g, 14.8 mmol), tert-butyl 3-amino-S-methyl- 1H-pyrazole-1-carboxylate (3.5 g, 17.7 mmol), cesium carbonate (9.61 g, 29.6 mmol) andPd Xphos (2.32 g, 2.95 mmol) were dissolved in dioxane (130 mL) and purged with nitrogen. The reaction mixture was stirred at 110 C for 12 h. The product was combined with the product of a similar reaction, extracted with EtOAc (600 mL) and washed with brine (3 x 300 mL). The organic layer was evaporated. The residue was crystallized to provide the title intermediate (5 g, 58 % yield) and 2 g of cmde product which waspurified by preparative HPLC (method 2).

Statistics shows that tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate is playing an increasingly important role. we look forward to future research findings about 578008-32-9.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; HUDSON, Ryan; KOZAK, Jennifer; FATHEREE, Paul R.; PODESTO, Dante D.; BRANDT, Gary E.L.; FLEURY, Melissa; BEAUSOLEIL, Anne-Marie; HUANG, Xiaojun; THALLADI, Venkat R.; (121 pag.)WO2016/191524; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 578008-32-9, A common heterocyclic compound, 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, molecular formula is C9H15N3O2, 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 10; 3-{[4-(Azetidin-l-ylcarbonyl)phenvnoxy}-iV-(5-methyl-lH-pyrazol-3-yl)- 5- [(3S)-tetr ahydrofur an-3-yloxyl benzamide; l-Chloro-N,N,2-trimethyl-l-propenylamine (0.145 mL, 1.10 mmol) was added to a solution of 3-{ [4-(azetidin- 1 -ylcarbonyl)phenyl]oxy } -5-[(3S)-tetrahydrofuran-3- yloxy]benzoic acid (350 mg, 0.92 mmol) in DCM (6 mL) and stirred at RT for 30 – 40min. 1,1-Dimethylethyl 3-amino-5-methyl-lH-pyrazole-l-carboxylate (361 mg, 1.83 mmol) and pyridine (0.148 mL, 1.83 mmol) were added and the reaction stirred at RT for 2 hours. The solvent was removed in vacuo, water (20 mL) added and the mixture extracted with ethyl acetate (3 x 20 mL). The extracts were combined and washed with 2Nu hydrochloric acid (20 mL), a saturated solution of sodium bicarbonate (20 mL), water (20 mL), brine (20 mL), dried (MgSO4) and evaporated in vacuo. The crude product was chromatographed on silica, eluting with a gradient of 0- 10% methanol in DCM, to give a white solid which was taken up in acetonitrile (2 mL) and heated in a microwave reactor at 160C for 10 minutes. EPO The reaction mixture was evaporated and the residue chromatographed on silica, eluting with 0-5% methanol in DCM, to give the desired compound as a white foam (50 mg). 1H NMR delta (CDCl3): 2.11 – 2.29 (m, 2H), 2.32 (s, 3H), 2.32 – 2.40 (m, 2H), 3.88 – 4.02 (m, 4H), 4.23 (t, 2H), 4.35 (t, 2H), 4.95 – 4.99 (m, IH), 6.56 (s, IH), 6.71 (t, IH), 7.02 (d, 2H), 7.13 (s, IH), 7.21 (s, IH), 7.64 (d, 2H), 9.06 (s, IH); m/z 463 (M+H)+, 461 (M-H)’

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; WO2007/17649; (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. 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate

3-(6-(5-Methyl-lH-pyrazol-3-ylamino)pyrazin-2- ylamino)benzonitrile. 3-(6-chloropyrazin-2-ylamino)benzonitrile (0.32 g, 1.39 mmol), tert-butyl 3-amino-5-methyl-lH-pyrazole-l-carboxylate (0.3 g, 1.53 mmol), palladium acetate (31 mg, 10 mol%), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (160 mg, 20 mol%), and potassium carbonate (0.96g, 6.95 mmol) were suspended in dioxane (8 mL). The mixture was stirred in a sealed flask at 9O0C for 1 hour. The reaction mixture was cooled, diluted with ethyl acetate (50 mL), washed with water (50 mL), and then with brine (30 mL). The organic layer was dried (sodium sulfate), filtered, and concentrated. The crude residue was dissolved in chloroform (20 mL) and 4N HCl in dioxane (3 mL) was added. The mixture was stirred at room temperature for 2 hours and the solvent evaporated. The crude product was purified by reverse-phase preparative HPLC (10-70% acetonitrile + 0.1% TFA in H2O + 0.1% TFA, over 30 min). Fractions containing product were condensed and neutralized on a Strata-XC ion exchange column (Phenomenex). The product was loaded and the column washed successively with water, acetonitrile, and methanol. The product was released with 5% ammonium hydroxide in methanol and product containing eluent was concentrated under reduced pressure and dried to give the title compound as a white solid (0.29g, 72% yield); m.p. 260-262C; 1H NMR (300 MHz, DMSCW6) delta 11.89 (br s, IH), 9.50 (s, IH), 9.38 (s, IH), 8.34 (s, IH), 7.89 (s, IH), 7.69 (dd, J, = 8.4 Hz, J2= 1.2 Hz, IH), 7.52 (s, IH), 7.43 (t, J= 8.4 Hz, IH), 7.31 (d, J= 7.6 Hz, IH), 6.05 (s, IH), 2.21 (s, 3H); MS (ESI) MS (ESI) m/z 292.0 [M+ 1]+.

The synthetic route of 578008-32-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2009/89042; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 578008-32-9 as follows. Recommanded Product: 578008-32-9

tert-Butyl 3-({3-[(1S)-2-methoxy-(1-methylethyl)oxy]-5-[4- (methylsulfonyl)phenoxy]benzoyl}amino)-5-methyl-1H-pyrazole-1-carboxylate; HATU (500 mg, 1.31 mmol) was added to 3-{(1S)-2-methoxy-(1-methylethyl)oxy}-5-{[4- (methylsulfonyl) phenyl] oxy} benzoic acid (400 mg, 1.05 mmol) followed by addition of DMF (6 mL), DIPEA (0.47 mL) and tert-butyl 3-amino-5-methyl-lH-pyrazole-l-carboxylate (380 mg, 1.93 mmol). The reaction was stirred under argon for 72 h, then dissolved in saturated aqueous sodium hydrogencarbonate (30 mL) and ethyl acetate (50 mL). The organic layer was separated, washed with saturated aqueous ammonium chloride (30 mL), then dried (MgS04), filtered and evaporated. Purification by column chromatography eluting with 1: 1 to 2: 1 ethyl acetate : hexanes afforded the title compound (500 mg, 85%) as a foam. 1H NMR 8 (CDC13) : 1.37 (d, 3H), 1.62 (s, 9H), 2.54 (s, 3H), 3.08 (s, 3H), 3.40 (s, 3H), 3.58 (m, 2H), 4.60 (m, 1H), 6. 82 (m, 2H), 7. 08 (m, 1H), 7.15 (d, 2H), 7.30 (s, 1H), 7.93 (d, 2H), 8.52 (brs, 1H); only 558 (M-H)-

According to the analysis of related databases, 578008-32-9, the application of this compound in the production field has become more and more popular.

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. 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate

2,6-Dichloropyrazine (5.0 g, 33.6 mmol), tert-butyl 3-amino-5-methyl-lH- pyrazole-1-carboxylate (6.62 g, 33.6 mmol), palladium(II) acetate (0.75 g, 3.36 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (3.88 g, 6.71 mmol), potassium carbonate (46.4 g, 336 mmol), and dioxane (224 mL) were combined and the mixture was degassed with nitrogen for 2 minutes before heating to 90C for one hour. The reaction was cooled to room temperature and filtered through Celite followed by washing with dichloromethane. The filtrate was condensed and the crude material was purified by silica gel chromatography (10-70% ethyl acetate in hexanes) to give the title compound as a white solid (6.43 g, 20.8 mmol, 62% yield); MS (ESI) MS (ESI) m/z 310.5 [M+l]+.

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 578008-32-9.

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 578008-32-9 as follows. Quality Control of tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate

A mixture of tert-butyl ((1R,3s,55)-3-((7-chloro- 1 ,6-naphthyridin-5-yl)amino)-8- azabicyclo[3.2.ljoctane-8-carboxylate (30 g, 77 mmol), tert-butyl 3-amino-5-methyl-1H- pyrazole-1-carboxylate (19.78 g, 100 mmol), Cs2CO3 (50.3 g, 154 mmol), PdXPhos(1.517 g, 1.93 mmol) and XPhos (0.919 g, 1.93 mmol) was degassed with nitrogen 3 times, and then 1,4-dioxane (300 mL) was added. The reaction mixture was degassed with nitrogen 5 times, heated to reflux, stirred for 16 h, and cooled to 75 C. Water (90 mL) was added and the reaction mixture was heated to reflux and stirred at reflux for48 h. Water (210 mL) was added slowly and the reaction mixture was stirred at RT fort 1 h, and filtered. The filter cake was washed with 1:1 dioxane:water (50 mL) and dried at 50 C under vacuum overnight to give crude title intermediate (35.34 g).The crude product was dissolved in DMF (173 mL). SiliaMetS thiol functionalized silica (8.65 g) was added and the reaction mixture was stirred for 45 mm at80 C, cooled to RT, filtered, and rinsed with DMF (35 mL). To the filtrate was added water (346 mL) dropwise and seeds from a previous preparation by the same procedure. The reaction mixture stirred at RT for 6 h, filtered, washed with water (35 mL) and dried at 50 C under vacuum to give the title intermediate (33.6 g, 97 % yield). HPLC Method 3 Retention time 16.89 mm

According to the analysis of related databases, 578008-32-9, the application of this compound in the production field has become more and more popular.

Reference of 578008-32-9, The chemical industry reduces the impact on the environment during synthesis 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, I believe this compound will play a more active role in future production and life.

Example 13Preparation of 3-(4-fluorophenylsulfinyl)-N-( -methyl-lH-pyrazol-3- vDisoq uinolin- 1-amine[00258] A sealed tube was charged with Pd2(dibenzylideneacetone)3 (14 mg,0.016 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (26 mg, 0.047 mmol), tert-butyl 3 -amino-5 -methyl- lH-pyrazole-l-carboxylate from Example 1 Step D (177 mg, 0.89 mmol), Na2C03 (1 10 mg, 1.04 mmol), l-bromo-3-(4- fluorophenylsulfinyl)isoquinoline from Example 10 Step D (260 mg, 0.74 mmol) and degassed toluene (5.2 mL), and then water (0.014 mL) was added with stirring. The sealed tube was heated in an oil bath at 100 C for 2 h, and then in a microwave synthesizer at 100 C for 1.5 h. The mixture was filtered and the filtrate was concentrated. The solid residue was triturated with MeOH and collected by filtration and dried under reduced pressure to afford tert-butyl 3-(3-(4- fluorophenylsulfinyl)isoquinolin- 1 -ylamino)-5 -methyl- 1 H-pyrazole- 1 -carboxylate (166 mg, 40 %) as a white solid. JH NMR (300 MHz, DMSO-t/6) delta 1.52 (s, 9H), 2.25 (s, 3H), 6.46 (s, 1H), 7.40 (t, 2H), 7.83-7.90 (m, 4H), 8.00-8.03 (m, 2H), 8.17 (d, 1H), 10.61 (s, 1H); LC-MS (ESI) m/z 467 (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, tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Related Products of 578008-32-9, 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. 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Step 2: Synthesis of tert-Butyl 3-((4-(4-methoxy-4-(methoxycarbonyl)cyclohexyl)-6- methylpyrimidin-2-yl)amino)-5-methyl-lH-pyrazole-l -carboxylate. (0298) Methyl 4-(2-chloro-6-methylpyrimidin-4-yl)- 1-methoxycyclohexane- 1-carboxylate (70.5 mg, 0.236 mmol), tert-butyl 3-amino-5-methyl-lH-pyrazole-l-carboxylate (69.8 mg, 0.354 mmol), di-tert-butyl(2′,4′,6′-triisopropyl-[l, -biphenyl]-2-yl)phosphine (20.0 mg, 0.2 equiv.), Pd2(dba)3 (21.6 mg, 0.1 equiv.), and potassium acetate (70 mg, 0.71 mmol) were combined in a vial under nitrogen and 0.98 mL dioxane was added. The reaction mixture was heated to 115 C for 2 h, then cooled to ambient temperature. The reaction mixture was diluted with EtOAc, filtered through celite, concentrated onto silica gel, and the resulting residue was purified by flash-column chromatography on silica gel (gradient elution, 0 to 100% ethyl acetate-hexanes) to give tert-butyl 3-((4-(4-methoxy-4-(methoxycarbonyl)cyclohexyl)-6-methylpyrimidin-2- yl)amino)-5-methyl-lH-pyrazole-l-carboxylate (48 mg, 44%) as a yellow oil. MS (ES+) C23H33N505 requires: 459, found: 460 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate. I believe this compound will play a more active role in future production and life.

Adding a certain compound to certain chemical reactions, such as: 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, 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 578008-32-9, HPLC of Formula: C9H15N3O2

A reaction vessel was charged with 6-chloro-N-[(l¡ê)-l-(5-fluoropyrimidm-2-yl)emyl]pyrazm-2- amine (Intermediate 9, 118 mg, 0.47 mmol), tert-butyl 3-amino-5-methyl-lH-pyrazole-l- carboxylate (Intermediate 10, 103 mg, 0.52 mmol), Cs2CO3 (459 mg, 1.14 mmol), Xantphos (14 mg, 0.024 mmol) and Pd2(dba)3 (7 mg, 0.012 mmol) and purged with nitrogen for 10 minutes. Dioxane (0.15 M) was then added to the tube and the reaction mixture was purged with nitrogen for another 10 minutes. The reaction mixture was heated at 1000C overnight. The reaction mixture was filtered through a plug of diatomaceous earth, diluted with EtOAc, washed with nuaetaCO3(aq) and brine, and dried (Na2SO4). The solvent was removed in vacuo to give a yellow residue (181 mg), which was purified with a Gilson column (10-35% MeCN/H2O, 15 min). The title compound was collected as a yellow solid (18.9 mg). LCMS: [M+H]+ 315. 1H NMR (300 MHz5 DMSO-d6) delta: 9.69 (s, 1 H) 8.94 (s, 2 H) 7.77 (br.s, 1 H) 7.53 (s, 1 H) 7.43 (s, 1 H) 6.03 (s, 1 H) 5.68 (s, 1 H) 5.24 (m, 1 H) 2.27 (s, 3 H) 1.60 (d, 3 H).

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