Sources of common compounds: Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate

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.

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. 309740-49-6, name is Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 1-methyl-4-nitro-1H-pyrazole-5-carboxylate

General procedure: To a solution of intermediate 488 (2.26 g, 9.45 mmol) in dry DCM (25.4 mL) was added dropwise diisobutylaluminium hydride (3.62 mL, 20.31 mmol) at – 50 C. The reaction mixture was stirred at – 50 C for 3 h then at rt for 2 h. The mixture was acidified at 0 C with a 3N aqueous solution of HCl and diluted with Et20. The organic layer was separated, washed with a IN aqueous solution of HCl, then twice with brine, dried over MgS04 and evaporated in vacuo. The residue (2.17 g) was purified by column chromatography on silica gel (irregular SiOH, 40 muiotaeta, 40 g, mobile phase: heptane/EtOAc, gradient from 100:0 to 60:40). The pure fractions were combined and the solvent was evaporated to give 536 mg of intermediate 489 (27% yield).

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; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (472 pag.)WO2018/2217; (2018); A1;,
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A new synthetic route of 118430-73-2

According to the analysis of related databases, 118430-73-2, the application of this compound in the production field has become more and more popular.

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 118430-73-2 as follows. Formula: C8H15N3

Example I; Synthesis Example I (Preparation of Exemplified compound (1)); [Show Image] A mixture of 41.4 g of 4-nitroaniline (0.3 mol), 84 ml of conc. hydrochloric acid, 60 ml of acetic acid and 84 ml of propionic acid was stirred at an inner temperature ranging from 0 C to 5C. To the mixture was dropped 20.7 g (0.3 mol) of sodium nitrite per 45 ml of water at an inner temperature of 5 C or less. Thereafter, stirring was continued for 30 minutes at an inner temperature ranging from 0 C to 5 C. The resultant diazonium salt solution was dropped to 600 ml of acetonitrile solution containing 46.0 g (0.3 mol) of 5-tert-butyl-2-methyl-2H-pyrazole-3-ylamine at an inner temperature of 10 C or less. After the dropwise addition of the diazonium salt solution, the resultant reaction solution was kept stirring for 2 hours, followed by injection of 1000 ml of water. Then, the precipitated azo dye was separated by a filtration. Recrystallization of the produced crystals was performed with 1650 ml of methanol, to obtain Exemplified compound (1). Yield: 72 g (80%), Melting point: 199 C to 201 C. lambdamax (ethyl acetate solution) of Exemplified compound (1) was 444 nm.

According to the analysis of related databases, 118430-73-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJIFILM Corporation; EP1903078; (2008); A2;,
Pyrazole – Wikipedia,
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New downstream synthetic route of 67-51-6

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

Synthetic Route of 67-51-6, 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. 67-51-6, name is 3,5-Dimethyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: SOCl2 (5 mL) was added to a round-bottom flask, and then 1a-i(1.0 mmol) and a catalytic amount of DMF (0.1 mmol) were added. Themixture was heated to reflux for 4 h (reaction monitored by HPLC),then excess SOCl2 was evaporated under reduced pressure. The residuewas dispersed in H2O (200 mL) and extracted with AcOEt. The organicphase was separated, dried, and concentrated. It was then purified byflash column chromatography (eluent: ethyl acetate/petroleum ether,1 : 10 v/v) to afford 2a-i.

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

Reference:
Article; Li, Yi; Liu, Yuanyuan; Xu, Guanghui; Chen, Kai; He, Guangke; Huang, Bin; Journal of Chemical Research; vol. 38; 11; (2014); p. 658 – 661;,
Pyrazole – Wikipedia,
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Some tips on 1-Methyl-1H-pyrazol-5-amine

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.

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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., COA of Formula: C4H7N3

3rd Generation BrettPhos precatalyst (31.1 mg, 0.03 mmol) was added to (iS)-2-(2-chloro- 5-methylpyrimidin-4-yl)-6-methyl-7-((4-(trifluoromethyl)pyridin-2-yl)mdihydroimidazo[l,2-a]pyrazin-8(5H)-one (Intermediate 80; 300 mg, 0.69 mmol), 1-methyl- lH-pyrazol-5-amine (167 mg, 1.72 mmol) and CS2CO3 (448 mg, 1.37 mmol) in 1,4- dioxane (8 mL) at 25°C under nitrogen. The resulting mixture was stirred at 100 °C for 8 hours. The solvent was then removed under reduced pressure. The crude product was purified by flash silica chromatography, elution gradient 0 to 6percent MeOH in DCM. Compound containing fractions were evaporated to dryness to afford a yellow residue. This residue was purified further by preparative HPLC (XSelect CSH Prep C18 OBD column, 5mu silica, 19 mm diameter, 150 mm length), using decreasingly polar mixtures of water (containing 0.03percent NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford (5)-6-methyl-2-(5-methyl-2-((l-methyl- lH-pyrazol-5-yl)amino)pyrimidin-4-yl)-7-((4-(trifluoromethyl)pyridin-2-yl)methyl)-6,7- dihydroimidazo[l,2-a]pyrazin-8(5H)-one (Example 28; 141 mg, 41.3percent) as a white solid. ^ NMR ^OO MHz, DMSO, 20 °C) delta 1.21 (3H, d), 2.52 (3H, s), 3.71 (3H, s), 4.13 (IH, dd), 4.37 (IH, dd), 4.52 (IH, dd), 4.58 (IH, d), 5.26 (IH, d), 6.31 (IH, d), 7.34 (IH, d), 7.71 (IH, d), 7.82 (IH, s), 7.95 (IH, s), 8.33 (IH, s), 8.84 (IH, d), 9.24 (IH, s). m/z (ES+), [M+H]+ = 498.

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; WARD, Richard, Andrew; JONES, Clifford, David; SWALLOW, Steven; GRAHAM, Mark, Andrew; DOBSON, Andrew, Hornby; MCCABE, James, Francis; (223 pag.)WO2017/80979; (2017); A1;,
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The important role of 3-Bromo-1,5-dimethyl-1H-pyrazole

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.

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. 5744-80-9, name is 3-Bromo-1,5-dimethyl-1H-pyrazole, A new synthetic method of this compound is introduced below., Formula: C5H7BrN2

General procedure: A mixture of 19d (0.20 g, 0.81 mmol), bis(pinacolato)-diboron(0.44 g, 1.72 mmol), Pd(Ph3P)4 (0.050 g, 0.043 mmol), and KOAc (0.17 g, 1.72 mmol) in 1,4-dioxane/H2O (30 mL, v/v, 5/1) was stirred at 100 C for 4 h under argon. It was cooled to room temperature. 10a(0.20 g, 0.54 mmol), Pd(Ph3P)4 (0.030 g, 0.029 mmol), and K2CO3(0.16 g, 1.14 mmol) were added to the reaction mixture at room temperature,and the mixture was stirred at 100 C for 12 h under argon. It was cooled to room temperature, and H2O was added to the mixture.The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silicagel column chromatography (eluting with 0-10% MeOH in DCM) to afford 10c as a pale yellow solid (0.13 g, 52%). 1H NMR (300 MHz,DMSO-d6) delta 8.27 (s, 1H), 7.78-7.75 (m, 1H), 7.54 (s, 1H), 7.18-7.15(m, 1H), 6.88-6.87 (m, 1H), 6.15 (s, 1H), 6.02-5.93 (m, 1H), 5.82-5.76(m, 1H), 5.32-5.27 (m, 1H), 5.03 (s, 2H), 3.93 (s, 3H), 3.64 (m, 4H),3.33 (m, 4H); 13C NMR (75 MHz, DMSO-d6) delta 161.85, 158.29, 156.01,153.75, 152.72, 142.91, 140.24, 139.17, 138.42, 137.18, 131.81,128.07, 126.97, 126.44, 124.53, 119.49, 116.23, 97.23, 65.97, 60.28,51.65, 41.76; MS (ESI) m/z:460.3 [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:
Article; Yin, Yuan; Chen, Cheng-Juan; Yu, Ru-Nan; Shu, Lei; Zhang, Tian-Tai; Zhang, Da-Yong; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1562 – 1576;,
Pyrazole – Wikipedia,
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Discovery of 14521-80-3

The synthetic route of 14521-80-3 has been constantly updated, and we look forward to future research findings.

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. 14521-80-3, name is 3-Bromo-1H-pyrazole, A new synthetic method of this compound is introduced below., Safety of 3-Bromo-1H-pyrazole

Example 9. Synthesis of 4-(3-(3-oxa-9-azaspiro[5.5]undecan-9-yl)-lH-pyrazol-l- yl)-2-(2,6-difluorophenyl)-6,7-dihydro-5H-pyrrolo [3,4-b] pyridin-5-one, 1-9 Synthesis of compound 9.2. To a mixture of 1.4 (0.4g, 1.05mmol, l .Oeq) in 1 ,4- dioxane (5.0 ml) was added 3-Bromo-lH-pyrazole (0.169g, 1.15mmol, 1.1 eq) and K2CO3 (0.29g, 2.10mmol, 2.5eq). The reaction mixture was degassed for 10 min. under argon atmosphere, then Pd2(dba)3 (0.096 g, 0.01 mmol, O. leq) and Xantphos (0.121g, 0.2mmol, 0.2eq) were added, and again degassed for 5 min. The reaction was then heated at 100 C for 2 h. Upon completion of the reaction, reaction mixture was poured into water and product was extracted with EtOAc. Organic layers were combined, washed with brine solution, dried over Na2S04 and concentrated under reduced pressure to obtain crude which was purified by column chromatography to provide 9.2 (0.1 1 g, 21.4%). MS(ES): m/z 9 [M+H]+.

The synthetic route of 14521-80-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; MONDAL, Sayan; (342 pag.)WO2017/40757; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

A new synthetic route of 4-Bromo-1-methyl-1H-pyrazol-3-amine

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-1-methyl-1H-pyrazol-3-amine. I believe this compound will play a more active role in future production and life.

Application of 146941-72-2, 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. 146941-72-2, name is 4-Bromo-1-methyl-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A soln. of amine BB-34 (1 eq) and aldehyde or ketone BB-12 (1.05 to 1.1 eq) in MeOH (2 to 4 mL/mmol) was stirred for 1 h at RT. NaBI-U (1.6 to 2 eq) was added portionwise at 0C and the rxn mixture was stirred at a given temperature for a given time (see Table 52). It was quenched with H2O at 0C and extracted with EtOAc. The combined org. phases were washed with brine, dried over MgSCh and concentrated in vacuo. When necessary, the crude was purified by CC using EtOAc/MeOH

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-1-methyl-1H-pyrazol-3-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (266 pag.)WO2019/137927; (2019); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

Some tips on Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate

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.

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. 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Safety of Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate

According to the procedure of Buchwald et al . (J. Oxg. Chem. 2004, 69, 5578), to a 350 iaL sealed tube flushed vigorously with nitrogen was added ethyl 3- (trifluoromethyl) – lH-pyrazole-4-carboxylate (20.0 g, 96.1 mmol) , 1-iodobenzene (12.9 inL, 115 mmol), potassium carbonate (27.9 g, 202 mmol), copper(I) iodide (0.915 g, 4.80 mmol), and (IS, 2S) -N1,N2- dimethylcyclohexane-l,2-diamine (1.37 g, 9.61 mmol), followed by degassed (argon) toluene (100 mL) . The mixture was stirred for 24 hours at 1100C, cooled to room temperature, and filtered through a short silica pad which was thoroughly rinsed with toluene and AcOEt- The filtrate was concentrated in vacuo to give ethyl l-phenyl-3- (trifluoromethyl) -lH-pyrazole-4- carboxylate (21 g, 77%) as a solid: 1H NMR (400 MHz, CDCl3) delta 1.39 (t, 3H, J = 7.0 Hz), 4.37 (q, 2H, J = 7.0 Hz), 7.42 (m, IH), 7.52 (m, 2H), 7.72 (m, 2H), 8.48 (m, IH).

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/11130; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Brief introduction of 285984-25-0

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, its application will become more common.

Electric Literature of 285984-25-0,Some common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, molecular formula is C14H19N3, 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 saturated aq. solution of NaHCO3 (H mL) was added to a solution of 3-terf-butyl-1 -p-tolyl-1 H- pyrazol-5-amine (WO 2000043384) (206 mg, 0.900 mmol) in DCM (20 mL) and the mixture was cooled to O0C and stirred vigorously whilst trichloromethylchloroformate (325 mul_, 2.70 mmol) was added in a single portion. The vigorous stirring was continued at O0C for a further 80 min. The organic layer was separated and dried and was then evaporated in vacuo to provide 3-te/f-butyl-5-isocyanato-1-p-tolyl-1 /-/-pyrazole, Intermediate B1 as orange oil. This material was pumped for 30 min under high vacuum and was then taken up into THF (6.0 ml.) and kept under nitrogen at O0C and used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, its application will become more common.

Reference:
Patent; RESPIVERT LIMITED; ITO, Kazuhiro; STRONG, Peter; RAPEPORT, William, Garth; MURRAY, Peter, John; KING-UNDERWOOD, John; WILLIAMS, Jonathan Gareth; ONIONS, Stuart, Thomas; JOLY, Kevin; CHARRON, Catherine, Elisabeth; WO2010/67130; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Share a compound : C4H5N3O2

The synthetic route of 34334-96-8 has been constantly updated, and we look forward to future research findings.

Application of 34334-96-8,Some common heterocyclic compound, 34334-96-8, name is 3-Methyl-5-nitro-1H-pyrazole, molecular formula is C4H5N3O2, 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.

General procedure: Mcthancsulfonyl chloride (6.683 mL, 1.48 g/mL, 86.338 mmol) was added to a solution of 3-methoxy-3-methylbutanol (5 g, 42.31 mmol ) and Et-,N (17.661 mL, 0.728 g/mL, 127.059 mmol ) in DCM (477.33 mL, 1 .326 g/mL, 7452.28 mmol) at rt and the reaction mixture was stirred for 18h. Water was added. The organic layer was separated, washed with I N HCI(aq) then with brine before drying over MgSC>4. The organic layer was filtered and evaporated to afford a mixture on intermediate 778 and 778′ (10.3 g, quantitative yield ) that was used directly in the next step. Bromo-3-methoxypropane (1.20 mL, 10.51 mmol) was added at rt to a mixture of 5-nitro-lH-pyrazole (1.00 g, 8.84 mmol), 2 (2.35 g, 17.00 mmol) in DMF (10 mL).This reaction was stirred in a sealed tube at 120 C using one single mode microwave(Biotage Initiator EXP 60) with a power output ranging from 0 to 400 W for 30 min.Then, water was added and this mixture was extracted twice with EtOAc. The organic10 layers were mixed, dried over MgS04, filtered and the solvent was evaporated untildryness. The residue was purified by column chromatography on silica gel (IrregularSiOH, 40 |im, 80 g, mobile phase: gradient from 70% heptane, 29% EtOAc, 1% MeOH(+10% NH4OH) to 40% heptane, 52% EtOAc, 8% MeOH (+10% NH4OH)). The purefractions were collected and the solvent was evaporated until dryness to give 1.39 g of15 intermediate 56 (85% yield) and 267 mg of intermediate 56? (16% yield). Theseintermediates were used as it in the next step.

The synthetic route of 34334-96-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (472 pag.)WO2018/2217; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics