Category: 105434-90-0

These common heterocyclic compound, 105434-90-0, name is Ethyl 5-amino-1H-pyrazole-3-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. Formula: C6H9N3O2

Ethyl 5-amino-1H-pyrazole-3-carboxylate (1.55 g, 10 mmol), tert-butyl acetoacetate (1.65 mL, 10 mmol), 3-fluoro-(4-trifluoromethyl)benzaldehyde (1.92 g, 10 mmol) and sodium bicarbonate (2.52 g, 30 mmol) were heated at 70 C. in DMF (3 mL) overnight. The reaction mixture was allowed to cool then partitioned between ethyl acetate (30 mL) and water (30 mL). The aqueous layer was further extracted with ethyl acetate (20 mL) and the combined organics were dried by passing through a hydrophobic fit, and evaporated to give an orange oil. The residue was dissolved in a minimum amount of DCM and loaded onto a 50 g Si cartridge. The product was eluted with 0-50% ethyl acetate in cyclohexane. The fractions containing the desired product were combined and evaporated to give a pale yellow solid. The solid was triturated with ethyl acetate/cyclohexane to give a white solid (1.25 g). LCMS (Method 3): Rt=1.36 min, m/z 470.5 [M+H]+

The synthetic route of Ethyl 5-amino-1H-pyrazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIESI FARMACEUTISI S.p.A.; Accetta, Alessandro; Rancati, Fabio; Capelli, Anna Maria; Clark, David Edward; Tisselli, Patrizia; Edwards, Christine; Bhalay, Gurdip; (97 pag.)US2018/170939; (2018); 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 105434-90-0 as follows. Application In Synthesis of Ethyl 5-amino-1H-pyrazole-3-carboxylate

[00383] To a solution of ethyl 5-amino-1H-pyrazole-3-carboxylate (1.55 g, 10 mmol) in AcOH (20 mL) was added 4,4,4-trifluoro-1-(4-methoxyphenyl)butane-1,3-dione (2.71 g, 11 mmol). The mixture was refluxed for 5 h and subsequently cooled down to 0 C in an ice bath. The precipitate was collected by filtration and recrystallized by hexanes/ethyl acetate to give a yellow solid. The solid was taken in MeOH (20 mL) and NaOH aq. (1M, 20 mL), and the solution was stirred at room temperature for 5 h. The solvent was then removed and the residue was acidified by 1M HC1 until PH 2. The precipitate was collected by filtration, and washed with cold water. The resulting solid was dried to obtain the pure product as a pale yellow solid (1.55 g, 92% yield). ?H NMR (400 MHz, DMSO-d6) oe 13.57 (s, 1H), 8.26-8.22 (m, 3H), 7.39 (d, J = 7.9 Hz, 2H), 7.32 (s, 1H), 2.39 (s, 3H).

According to the analysis of related databases, 105434-90-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; MARKOWITZ, Sanford D.; YUAN, Yiyuan; ZHANG, Yongyou; READY, Joseph; HU, Bin; (228 pag.)WO2018/145080; (2018); 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 105434-90-0 as follows. Application In Synthesis of Ethyl 5-amino-1H-pyrazole-3-carboxylate

[00383] To a solution of ethyl 5-amino-1H-pyrazole-3-carboxylate (1.55 g, 10 mmol) in AcOH (20 mL) was added 4,4,4-trifluoro-1-(4-methoxyphenyl)butane-1,3-dione (2.71 g, 11 mmol). The mixture was refluxed for 5 h and subsequently cooled down to 0 C in an ice bath. The precipitate was collected by filtration and recrystallized by hexanes/ethyl acetate to give a yellow solid. The solid was taken in MeOH (20 mL) and NaOH aq. (1M, 20 mL), and the solution was stirred at room temperature for 5 h. The solvent was then removed and the residue was acidified by 1M HC1 until PH 2. The precipitate was collected by filtration, and washed with cold water. The resulting solid was dried to obtain the pure product as a pale yellow solid (1.55 g, 92% yield). ?H NMR (400 MHz, DMSO-d6) oe 13.57 (s, 1H), 8.26-8.22 (m, 3H), 7.39 (d, J = 7.9 Hz, 2H), 7.32 (s, 1H), 2.39 (s, 3H).

According to the analysis of related databases, 105434-90-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CASE WESTERN RESERVE UNIVERSITY; BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; MARKOWITZ, Sanford D.; YUAN, Yiyuan; ZHANG, Yongyou; READY, Joseph; HU, Bin; (228 pag.)WO2018/145080; (2018); 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. 105434-90-0, name is Ethyl 5-amino-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Ethyl 5-amino-1H-pyrazole-3-carboxylate

Subsequently, to a solution of ethyl 5-amino-3-pyrazolecarboxylate (1.337 g) in tetrahydrofuran (15 mL) was added pyridine (1.385 mL), and then a solution of 4,5-difluoro-2-methyl-benzoyl chloride in tetrahydrofuran (2 mL) was added dropwise with ice cooling. After stirring overnight at room temperature, ethanol (5 mL) and water (45 mL) were added to the reaction mixture, and the precipitated solid was collected by filtration to obtain the title compound (2.271 g) as a white solid.

The synthetic route of 105434-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JAPAN TOBACCO, INC.; US2009/36450; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 105434-90-0, 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 105434-90-0 as follows.

There was dissolved, in ethanol (3 mL), ethyl 5-amino-1H-pyrazole-3-carboxylate (201 mg, 1.30 mM) and then sodium ethoxide (195 g, 2.86 mM) and diethyl malonate (217 muL, 1.43 mM) were added to the solution. This reaction liquid was stirred for 8 hours, while refluxing the same with heating. This reaction mixture was filtered and then the resulting solid was washed with diethyl ether. After the addition of phosphoryl chloride (10 mL) to the resulting solid with ice-cooling, the resulting suspension was stirred for 3 hours, while refluxing the same with heating. The phosphoryl chloride was distilled off from the reaction liquid, ethanol was then added to the residue with ice-cooling and then the mixture was stirred for 15 minutes. After the concentration of this reaction liquid, the resulting concentrate was purified by the silica gel column chromatography (methanol/methylene chloride=1:100) to thus give the title compound (49.5 mg, overall yield of these two steps: 15%). 1H-NMR (300 MHz, CDCl3): delta 1.45 (t, 3H, J=7.2 Hz), 4.50 (q, 2H, J=7.2 Hz), 7.11 (s, 1H), 7.23 (s, 1H); MS (ESI) m/z 259 (M+H)+.

According to the analysis of related databases, 105434-90-0, the application of this compound in the production field has become more and more popular.

Synthetic Route of 105434-90-0,Some common heterocyclic compound, 105434-90-0, name is Ethyl 5-amino-1H-pyrazole-3-carboxylate, molecular formula is C6H9N3O2, 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.

Ethyl 6-(2-ethoxy-2-oxoethyl)-7-hydroxy-5-methylpyrazolo[l,5-a]pyrimidine- 2-carboxylate. A suspension of ethyl 5-amino-lH-pyrazole-3-carboxylate (35.5 g, 229 mmol, prepared according to WO 2008015271), diethyl 2-acetylsuccinate (51.2 niL, 275 mmol) and TsOHH20 (0.218 g, 1.144 mmol) in o-xylene (500 mL) was refluxed using a Dean-Stork condensor for 5 h. (Note: The suspension turned into a clear homogeneous solution and then in about 15 min a yellow solid started precipitated out of solution). Then, the reaction mixture was cooled, diluted with hexanes (250 mL), filtered, washed with hexanes and dried to afford ethyl 6-(2- ethoxy-2-oxoethyl)-7-hydroxy-5-methylpyrazolo[ 1 ,5-a]pyrimidine-2-carboxylate (53 g, 75 % yield) as light yellow solid. 1H NMR (500 MHz, DMSO-d6) delta 12.61 (br. s., 1H), 6.49 (s, 1H), 4.34 (q, J= 7.1 Hz, 2H), 4.09 (q, J= 7.1 Hz, 2H), 3.57 (s, 2H), 2.34 (s, 3H), 1.33 (t, J= 7.2 Hz, 3H), 1.19 (t, J= 7.0 Hz, 3H). LCMS (M+l) = 308.04.

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

Electric Literature of 105434-90-0, The chemical industry reduces the impact on the environment during synthesis 105434-90-0, name is Ethyl 5-amino-1H-pyrazole-3-carboxylate, I believe this compound will play a more active role in future production and life.

LAH (20 mg, 0.51 mmol) was added to an ice cooled solution of ethyl 5-amino-l-((2-(5-phenylisoxazole-3-carboxamido)ethyl)sulfonyl)-lH- pyrazole-3-carboxylate (100 mg, 0.2537 mmol) in THF (10 mL) and the reaction mixture was stirred for 1 h at the same temperature. Then the reaction mixture was quenched with saturated NH4C1 solution and filtered through celite pad. The filtrate was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude compound which was further purified by preparative HPLC to obtain N-(2-((5-amino-3-(hydroxymethyl)-lH-pyrazol-l- yl)sulfonyl)ethyl)-5-phenylisoxazole-3-carboxamide (23 mg, 7% over two steps). (0261) [00169] Appearance: white solid (0262) [00170] Analytical data: XH NMR (400 MHz, DMSO-d6): delta 8.89-8.87 (m, IH), 7.94-7.92 (m, 2H), 7.58-7.54 (m, 3H), 7.36 (s, IH), 6.07 (s, D20 exchangeable, 2H), 5.34 (s, IH), 5.16 (t, J=6.0 Hz, IH), 4.25 (d, J=6.0 Hz, 2H), 3.76 (t, J=6.6 Hz, 2H), 3.61-3.56 (m, 2H). (0263) [00171] LC-MS: [M+H]+=391.9 (0264) [00172] HPLC Purity: 98.50% at 254 nm and 98.37% at 220 nm.

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, Ethyl 5-amino-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Electric Literature of 105434-90-0, These common heterocyclic compound, 105434-90-0, name is Ethyl 5-amino-1H-pyrazole-3-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.

A solution of 5-Amino~lH-pyrazole-3~carboxylic acid ethyl ester (0.0775 g, 0.500 mmol), benzaldehyde (0.064 g, 0.60 mmol) and sodium triacetoxyborohydride (0.212 g, 1.00 mmol) in dichloroethane (5 cm3) and stirred over night at 6O0C. The solution was diluted with further dichloroethane (10 cm3), was washed with NaHCO3, until there was no further gas evolution, then with brine. The organic phase was dried over anhydrous Na2SO4, filtered, and solvent removed under reduced pressure to give a brown oil. The crude product was taken into acetonitrile (3 cm3) and purified by preparatory HPLC to give 5-benzylamino-lH-pyrazole-3- carboxylic acid ethyl ester.5-Benzylamino-lH-pyrazole-3-carboxylic acid ethyl ester was taken up in IM lithium hydroxide: tetrahydrofuran : methanol (1 : 5 : 1) (10 cm3)and heated at reflux over night. Solvent EPO was removed under reduced pressure and the crude product was acidified to pH 1 with 0.1M HCl and extracted with ethyl acetate (10 cm3). The organic phase was dried over anhydrous Na2SO4, filtered, and solvent removed under reduced pressure to give a brown, glassy solid. 1H (DMSO- d6): 7.35-7.2 (m, 5H, CH2C6H5), 6.0 (s, IH), 4.5 (s, 2H, CH2C6H5). m/z (ES+): 218 [M+H]+

Statistics shows that Ethyl 5-amino-1H-pyrazole-3-carboxylate is playing an increasingly important role. we look forward to future research findings about 105434-90-0.

Application of 105434-90-0,Some common heterocyclic compound, 105434-90-0, name is Ethyl 5-amino-1H-pyrazole-3-carboxylate, molecular formula is C6H9N3O2, 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 mixture of compound 226-1 (1.0 g, 6.45 mmol) in THF (10 mL) was added LiBH4 (8.0 mL,16.01 mmol, 2M in THF) drop- wisely at 0 oC and the reaction was stirred at 60 oC overnight. After completion of the reaction, the reaction mixture was quenched with MeOH and concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel (DCM: MeOH = 80: 1 to 20: 1) to give compound 2 (600 mg, yield 82.3%) as white solid. LC/MS (ESI) m/z: 114 (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 Ethyl 5-amino-1H-pyrazole-3-carboxylate, its application will become more common.

Application of 105434-90-0,Some common heterocyclic compound, 105434-90-0, name is Ethyl 5-amino-1H-pyrazole-3-carboxylate, molecular formula is C6H9N3O2, 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 suspension of ethyl 5-amino-1H-pyrazole-3-carboxylate (35.5 g, 229 mmol, prepared according to WO 2008015271), diethyl 2-acetylsuccinate (51.2 mL, 275 mmol) and TsOH.H2O (0.218 g, 1.144 mmol) in o-xylene (500 mL) was refluxed using a Dean-Stork condenser for 5 h. (Note: The suspension turned into a clear homogeneous solution and then in about 15 min a yellow solid started precipitated out of solution). Then, the reaction mixture was cooled, diluted with hexanes (250 mL), filtered, washed with hexanes and dried to afford ethyl 6-(2-ethoxy-2-oxoethyl)-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (53 g, 75% yield) as light yellow solid. 1H NMR (500 MHz, DMSO-d6) delta 12.61 (br. s., 1H), 6.49 (s, 1H), 4.34 (q, J=7.1 Hz, 2H), 4.09 (q, J=7.1 Hz, 2H), 3.57 (s, 2H), 2.34 (s, 3H), 1.33 (t, J=7.2 Hz, 3H), 1.19 (t, J=7.0 Hz, 3H). LCMS (M+1)=308.04.

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