Category: 78703-53-4

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 78703-53-4 as follows. Application In Synthesis of 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid

General procedure: 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid of formula (III) (7.76 g, 40 mmol)Reflowed with thionyl chloride (47.6 g, 0.4 mol) for 4 hours.When the reaction system turns into a pale yellow transparent liquid,Continue to react for 30 minutes,The reaction stops,After cooling to room temperature, it was distilled under reduced pressure.1,3-dimethyl-1H-pyrazole-4-yl chloride,1,3-Dimethyl-1H-pyrazole-4-yl chloride (2mmol)Add 15ml of dichloromethane,Join(R)-1-phenethyl-1-amine(2.1mmol),Then triethylamine (0.3 g, 3 mmol) was slowly added dropwise at room temperature overnight;TLC (EA: PE=2:1(V)) tracking,After the reaction was completed, it was extracted three times with a dichloromethane/water = 1:1 (V) system.Concentrated organic layer,Extracted with toluene or 75% ethanol,Column chromatography (EA: PE = 2:1 (V)),Obtained (K19)(R)-1,3-dimethyl-N-(1-phenethyl)-1H-pyrazole-4-carboxamide;

According to the analysis of related databases, 78703-53-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang University of Technology; Jin Tao; Wang Han; Tan Chengxia; Weng Jianquan; Han Liang; Liu Xinghai; (9 pag.)CN109156471; (2019); A;,
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. 78703-53-4, name is 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid

To a solution of 10b (578.8 g, 4.13 mol) in DMAC (2.0 L) at 0 C was added thionyl chloride (514.7 g, 4.33 mol) dropwise, maintaining the temperature below 15 C. After addition of DMAC (0.25 L), the mixture was stirred at 0-15 C for 0.5 h. To this mixture was added 8 (500.0 g, 3.93 mol) portionwise, maintaining the temperature below 40 C. After addition of DMAC (0.75 L), the mixture was stirred at 15-40 C for 1 h. Then, H2O (1.0 L), NaOH (346.1 g, 8.65 mol) in H2O (4.5 L), and H2O (3.5 L) were successively added dropwise at 15-40 C. The resulting slurry was stirred for 2 h, and then filtered. Wet solids were washed with H2O (1.5 L) and dried in vacuo at 50 C to give the title compound 13b (923 g, 94%) as a pale brown solid; mp 188-189 C; 1H NMR (500 MHz, DMSO-d6) delta 2.19 (s, 3H), 3.98 (s, 3H), 6.62 (ddd, 4JHF=3.3 Hz, J=8.5, 3.3 Hz, 1H), 6.83 (s, 1H), 7.02 (dd, 4JHF=6.5 Hz, J=3.0 Hz, 1H), 7.07 (dd, 3JHF=10.0 Hz, J=9.0 Hz, 1H), 9.48 (br s, 1H), 9.85 (s, 1H); 13C NMR (125 MHz, DMSO-d6) delta 13.0, 38.5, 107.5, 112.9, 112.9, 115.8 (2JCF=21.3 Hz), 125.0 (2JCF=12.5 Hz), 135.2, 145.4, 149.0 (1JCF=235.0 Hz), 153.3 (3JCF=1.3 Hz), 158.0; IR (ATR) 3229, 1651, 1625, 1547, 1531, 1504, 1452, 1377, 1303, 1274, 1260, 1226, 1178, 1109, 1056, 1024, 973, 893, 850, 817, 804, 788, 771, 746, 678, 638, 624, 595, 527, 510, 461, 451, 432, 422, 412 cm-1; Anal. Calcd for C12H12N3O2F: C, 57.83; H, 4.85; N, 16.86. Found: C, 57.62; H, 4.69; N, 16.88.

The synthetic route of 78703-53-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ishimoto, Kazuhisa; Sawai, Yasuhiro; Fukuda, Naohiro; Nagata, Toshiaki; Ikemoto, Tomomi; Tetrahedron; vol. 69; 40; (2013); p. 8564 – 8571;,
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. 78703-53-4, name is 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid

A solution of 3-(4-chloro-2-methylphenyl)piperidine hydrochloride (50 mg, 0.203 mmol) (Intermediate la5) in DCM (10 mL) was treated with 1,3 -dimethyl- lH-pyrazole-4- carboxylic acid (31.3 mg, 0.223 mmol), l-ethyl-3-(3-dimethylaminopropyl)carbodimide hydrochloride (48.7 mg, 0.254 mmol), 1-hydroxybenzotriazole hydrate (34.8 mg, 0.227 mmol) and triethylamine (0.057 mL, 0.406 mmol). The mixture was stirred at room temperature for 17 hours. Water was added to the reaction mixture which was stirred vigorously for 30 minutes before the phases were separated using a phase separation cartridge. The organic phase was concentrated in vacuo. The crude product was purified by preparative LCMS (basic conditions) to give the title compound 3-(4-chloro-2- methylphenyl)-l-[(l,3-dimethyl-lH-pyrazol-4-yl)carbonyl]piperidine (42 mg, 62%). 1H NMR (400 MHz, DCM-d2) delta ppm 1.57 – 2.07 (m, 4 H) 2.32 (s, 6 H) 2.78 – 3.07 (m, 3 H) 3.87 (s, 3 H) 4.12 – 4.52 (m, 2 H) 7.14 – 7.22 (m, 3 H) 7.45 (s, 1 H) MS ES+: 332

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 78703-53-4.

Reference:
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BOUSBA, Sarah; GOLDBY, Anne; JENKINS, Kerry; KINSELLA, Natasha; TEALL, Martin; WO2015/19103; (2015); 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 78703-53-4 as follows. Computed Properties of C6H8N2O2

1,3-Dimethyl-1H-pyrazole-4-carboxylic acid of formula (III) (7.76 g, 40 mmol)Reflowed with thionyl chloride (47.6 g, 0.4 mol) for 4 hours.When the reaction system turns into a pale yellow transparent liquid,Continue to react for 30 minutes,The reaction stops,After cooling to room temperature, it was distilled under reduced pressure.1,3-dimethyl-1H-pyrazole-4-yl chloride,1,3-Dimethyl-1H-pyrazole-4-yl chloride (2mmol)Add 15ml of dichloromethane,Join(R)-1-phenethyl-1-amine(2.1mmol),Then triethylamine (0.3 g, 3 mmol) was slowly added dropwise at room temperature overnight;TLC (EA: PE=2:1(V)) tracking,After the reaction was completed, it was extracted three times with a dichloromethane/water = 1:1 (V) system.Concentrated organic layer,Extracted with toluene or 75% ethanol,Column chromatography (EA: PE = 2:1 (V)),Obtained (K19)(R)-1,3-dimethyl-N-(1-phenethyl)-1H-pyrazole-4-carboxamide;

According to the analysis of related databases, 78703-53-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang University of Technology; Jin Tao; Wang Han; Tan Chengxia; Weng Jianquan; Han Liang; Liu Xinghai; (9 pag.)CN109156471; (2019); A;,
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 78703-53-4 as follows. Safety of 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid

A mixture of tert-butyl [2-(3-chloro-5-fluorobenzyl)-4-methyl-1,3-thiazol-5-yl]carbamate (500 mg, 1.40 mmol) obtained in Example 145-E), concentrated hydrochloric acid (1 mL) and ethanol (2 mL) was stirred at 50C for 1 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in DMF (3 mL), 1,3-dimethyl-1H-pyrazole-4-carboxylic acid (216 mg, 1.54 mmol), HATU (585 mg, 1.54 mmol) and DIEA (0.12 mL, 0.70 mmol) were added, and the mixture was stirred at 60C for 4 hr. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography [eluent: ethyl acetate-methanol (100:0-80:20)]. The obtained solid was crystallized from heptane-ethyl acetate to give the title compound (40 mg) as a pale-brown solid (yield 8%). MS (ESI+): [M+H]+ 379. 1H NMR (300 MHz, CDCl3) delta 2.39 (3H, s), 2.55 (3H, s), 3.88 (3H, s), 4.18 (2H, s), 6.90-7.01 (2H, m), 7.08-7.12 (1H, m), 7.46 (1H, s), 7.81 (1H, s). mp 125-128C

According to the analysis of related databases, 78703-53-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2530078; (2012); 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 78703-53-4 as follows. Recommanded Product: 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid

General procedure: 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid of formula (III) (7.76 g, 40 mmol)Reflowed with thionyl chloride (47.6 g, 0.4 mol) for 4 hours.When the reaction system turns into a pale yellow transparent liquid,Continue to react for 30 minutes,The reaction stops,After cooling to room temperature, it was distilled under reduced pressure.1,3-dimethyl-1H-pyrazole-4-yl chloride,1,3-Dimethyl-1H-pyrazole-4-yl chloride (2mmol)Add 15ml of dichloromethane,Join(R)-1-phenethyl-1-amine(2.1mmol),Then triethylamine (0.3 g, 3 mmol) was slowly added dropwise at room temperature overnight;TLC (EA: PE=2:1(V)) tracking,After the reaction was completed, it was extracted three times with a dichloromethane/water = 1:1 (V) system.Concentrated organic layer,Extracted with toluene or 75% ethanol,Column chromatography (EA: PE = 2:1 (V)),Obtained (K19)(R)-1,3-dimethyl-N-(1-phenethyl)-1H-pyrazole-4-carboxamide;

According to the analysis of related databases, 78703-53-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang University of Technology; Jin Tao; Wang Han; Tan Chengxia; Weng Jianquan; Han Liang; Liu Xinghai; (9 pag.)CN109156471; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 78703-53-4, A common heterocyclic compound, 78703-53-4, name is 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid, molecular formula is C6H8N2O2, 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 ethyl acetoacetate (40 mmol) and triethyl orthoformate (60 mmol) in acetic anhydride (0.12 mol) was refluxed for 8 hours. After completion of the reaction, the product was distilled under reduced pressure to give crude product (1).Then, the intermediate (1) (40 mmol) was added dropwise to a mixture of methylhydrazine (60 mmol) and ethanol (20 mL) and reacted at 60 C for 8 hours. After completion of the reaction, the residue was distilled under reduced pressure, (20 mL) was extracted with saturated brine, and the organic layer was partitioned with anhydrous sodium sulfate and evaporated to give 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylate (2) The pyrazole ester 2 was stirred at room temperature for 12 hours in a solution of sodium hydroxide in ethanol. After removing the solvent ethanol, the solid was dissolved in water, hydrochloric acid was added, and a white solid 3 was precipitated.A solution of 14 g (0.1 mol) of 1,3-dimethyl-1H-pyrazole-4-carboxylic acid (3) was charged into a 250 mL single-necked flask, 75 mL of SOCl2 was added slowly, heated under reflux for 4 h, and the reaction was complete by TLC. SOCl2 to give a pale yellow solid. 2.5 mmol of thiocyanate was dissolved in 15 ml of anhydrous acetonitrile, and then two drops of PEG-200 were added to the mixture, followed by stirring at room temperature for 5 min.Subsequently, 1 mmol of the acetonitrile solution of the compound 4 was added, and the mixture was stirred at room temperature for 40 minutes. The mixture was filtered to obtain an acetonitrile solution of pyrazolecarbonyl isothiocyanate and then substituted aniline (0.85 mmol) was added.After stirring at room temperature for 3-4 hours, the reaction mixture was evaporated in vacuo and the residue was subjected to silica gel column chromatography using petroleum ether and ethyl acetate as the solvent to give the product.

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; Zhejiang University of Technology; Liu Xinghai; Wang Han; Zhai Zhiwen; Shen Zhonghua; Tan Chengxia; Weng Jianquan; Wu Hongke; Sun Nabo; (10 pag.)CN107033082; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 78703-53-4, 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. 78703-53-4, name is 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

100 mL with spherical condenserA 1-dimethyl-1H-pyrazole-4-carboxylic acid (7.5 mmol) intermediate was added to a single-necked round bottom flask followed by the addition of 30 mmol of thionyl chloride under stirring. After refluxing for 4 hours, To give 1-methyl-3-methyl-1H-pyrazole-4-acid chloride (V)In step 2), the chlorinating reagent is one or more mixture of thionyl chloride, phosphorus oxychloride or phosphorus trichloride.

The synthetic route of 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Liu Xinghai; Zhao Wen; Shen Zhonghua; Peng Weili; Tan Chengxia; Weng Jianquan; (11 pag.)CN106632044; (2017); A;,
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. 78703-53-4, name is 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

Example 173 Production of N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-fluorophenyl]-1,3-dimethyl-1H-pyrazole-4-carboxamide To a solution of 1,3-dimethyl-1H-pyrazole-4-carboxylic acid (140 mg, 1.0 mmol) and N,N-dimethylformamide (2 drops) in tetrahydrofuran (10 mL) was added oxalyl chloride (0.171 mL, 2.0 mmol) with stirring under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in N-methylpyrrolidone (5 mL) with stirring under ice-cooling, N-[6-(3-amino-4-fluorophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (164 mg, 0.50 mmol) was added, and the mixture was stirred at room temperature for 18 hr. The reaction mixture was diluted with ethyl acetate (80 mL), and washed with 1N aqueous sodium hydroxide solution (10 mL) and water (10 mL*3). The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0?70/30) and recrystallized from ethyl acetate to give the title compound (88 mg, yield 39%) as a white solid. melting point 205 C. 1H-NMR (DMSO-d6, 300 MHz) delta 0.73-0.88 (4H, m), 1.86-1.99 (1H, m), 2.32 (3H, s), 3.81 (3H, s), 7.06 (1H, d, J=9.5 Hz), 7.06-7.14 (1H, m), 7.36 (1H, dd, J=10.2, 9.0 Hz), 7.66 (1H, dd, J=6.4, 3.2 Hz), 7.94 (1H, s), 8.03 (1H, d, J=9.5 Hz), 8.32 (1H, s), 9.53 (1H, s), 11.06 (1H, s).

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 78703-53-4.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/137595; (2009); 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. 78703-53-4, name is 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., COA of Formula: C6H8N2O2

To a solution of 10b (578.8 g, 4.13 mol) in DMAC (2.0 L) at 0 C was added thionyl chloride (514.7 g, 4.33 mol) dropwise, maintaining the temperature below 15 C. After addition of DMAC (0.25 L), the mixture was stirred at 0-15 C for 0.5 h. To this mixture was added 8 (500.0 g, 3.93 mol) portionwise, maintaining the temperature below 40 C. After addition of DMAC (0.75 L), the mixture was stirred at 15-40 C for 1 h. Then, H2O (1.0 L), NaOH (346.1 g, 8.65 mol) in H2O (4.5 L), and H2O (3.5 L) were successively added dropwise at 15-40 C. The resulting slurry was stirred for 2 h, and then filtered. Wet solids were washed with H2O (1.5 L) and dried in vacuo at 50 C to give the title compound 13b (923 g, 94%) as a pale brown solid; mp 188-189 C; 1H NMR (500 MHz, DMSO-d6) delta 2.19 (s, 3H), 3.98 (s, 3H), 6.62 (ddd, 4JHF=3.3 Hz, J=8.5, 3.3 Hz, 1H), 6.83 (s, 1H), 7.02 (dd, 4JHF=6.5 Hz, J=3.0 Hz, 1H), 7.07 (dd, 3JHF=10.0 Hz, J=9.0 Hz, 1H), 9.48 (br s, 1H), 9.85 (s, 1H); 13C NMR (125 MHz, DMSO-d6) delta 13.0, 38.5, 107.5, 112.9, 112.9, 115.8 (2JCF=21.3 Hz), 125.0 (2JCF=12.5 Hz), 135.2, 145.4, 149.0 (1JCF=235.0 Hz), 153.3 (3JCF=1.3 Hz), 158.0; IR (ATR) 3229, 1651, 1625, 1547, 1531, 1504, 1452, 1377, 1303, 1274, 1260, 1226, 1178, 1109, 1056, 1024, 973, 893, 850, 817, 804, 788, 771, 746, 678, 638, 624, 595, 527, 510, 461, 451, 432, 422, 412 cm-1; Anal. Calcd for C12H12N3O2F: C, 57.83; H, 4.85; N, 16.86. Found: C, 57.62; H, 4.69; N, 16.88.

The synthetic route of 78703-53-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ishimoto, Kazuhisa; Sawai, Yasuhiro; Fukuda, Naohiro; Nagata, Toshiaki; Ikemoto, Tomomi; Tetrahedron; vol. 69; 40; (2013); p. 8564 – 8571;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics