Day: June 2, 2021

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. 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate

Dissolve 2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-tert-butyl carboxylate 3a (2.8 g, 13.5 mmol) in acetonitrile (50 mL) and add 3-chloro Benzyl bromide (3.3 g, 16.2 mmol) and cesium carbonate (32.5 g, 47 mmol) were vented 3 times under nitrogen and placed in an 80 C oil bath for 3 hours. The reaction solution was filtered, and the filtrate was concentrated. The residue was purified by column chromatography (petroleum ether: ethyl acetate = 2: 1) to obtain 2-(3-chlorobenzyl)-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-tert-butyl carboxylic acid 3b (4.1 g, yellow oil), yield 91%.

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; Shanghai Meidixi Bio-pharmaceutical Co., Ltd.; Meidixipuya Pharmaceutical (Shanghai) Co., Ltd.; Ren Feng; Wang Xianlian; Xu Yongmei; Chen Chunlin; Cai Jinna; (28 pag.)CN110194773; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 162758-35-2, The chemical industry reduces the impact on the environment during synthesis 162758-35-2, name is 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid, I believe this compound will play a more active role in future production and life.

Scheme 3 depicts the conversion of the carboxylic acid from Scheme 1 to its acid chloride using thionyl chloride or oxalyl chloride in dichloroethane at ambient to elevated temperatures followed by treatment with an amine such as alanine ethyl ester (A=methyl, n=0) in the presence of triethylamine to afford the amide ester (step a). Hydrolysis of the ester with lithium hydroxide in aqueous THF solution and acidification with dilute hydrochloric acid solution should yield the amide carboxylic acid (step b). This acid can be further treated with Boc anhydride (Boc2O) in THF in the presence of pyridine, followed by a solution of ammonia in THF at 0 degrees to ambient temperature to yield the carboxamido compound (step c).

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, 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JENRIN DISCOVERY; US2007/213302; (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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 1H-Pyrazole-4-carbonitrile

To a solution of 2-chloro-/V-(2,4-dimethoxybenzyl)-5-nitrobenzenesulfonamide (15.0 g, 38.8 mmol) in acetonitrile (450 mL) were added 1 /-/-pyrazole-4-carbonitrile (5.41 g, 93.1 mmol) and powdered potassium carbonate (16.1 g, 1 16 mmol) and it was stirred overnight at 100C. The reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate and water. Pure title compound precipitated and was filtered off (9.09 g 20.5 mmol, 53 % yield, 97 % purity), The organic phase was washed with brine and dried over sodium sulfate. Concentration in vacuo led to further crude title compound (9.1 1 g., app. 60 % purity). (0390) LC-MS (Method B): Rt = 1 .17 min; MS (ESIneg): m/z = 442 [M-H]” (0391) 1H-NMR (400MHz, DMSO-d6) delta [ppm]: 3.53 (s, 3H), 3.64 (s, 3H), 4.08 (s, 2H), 6.20 (d, 1 H), 6.29 (dd, 1 H), 7.07 (d, 1 H), 7.89 (d, 1 H), 8.12 (br s, 1 H), 8.30 (br s, 1 H), 8.41 – 8.54 (m, 2H), 9.17 (br s, 1 H).

The synthetic route of 31108-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; HAUFF, Peter; WERNER, Stefan; (94 pag.)WO2019/81573; (2019); 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. 5744-80-9, name is 3-Bromo-1,5-dimethyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3-Bromo-1,5-dimethyl-1H-pyrazole

The title compound was obtained in analogy to example 48, intermediate a, from tert-butyl 4- oxo- 1 -phenyl- 1,3 ,8-triazaspiro [4. 5]decane-8-carboxylate (example 35, intermediate c) and 3- bromo-1,5-dimethyl-1H-pyrazole (CAS RN 5744-80-9) at 120C over 19 hours as a colorlesssolid. MS (ESI): mlz = 426.25 [M+H]; To a suspension of tert-butyl 4-oxo- 1 -phenyl- 1,3, 8-triazaspiro [4.51 decane- 8-carboxylate (100 mg, 302 imol, example 35, intermediate c) and 1-ethyl-3-iodo-1H-pyrazole (67 mg, 302 imol, CAS RN 120278 1-34-7) in dioxane (2 mL) were added K2C03 (125 mg, 905 imol), DMEDA(6.11 iL, 48.3 imol, CAS RN 110-70-3) and Cul (4.6 mg, 24.1 imol) and the mixture was purged with argon. The suspension was heated to 100C and stuffed at this temperature over 14 hours. The reaction mixture was filtered over a microfilter, the filtrate was washed with a small volume of EtOAc and MeOH, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 4 g column using an MPLC (ISCO) system elutingwith a gradient of n-heptane : EtOAc (100: 0 to 50: 50) to give the title compound as a colorless solid (0.107 g; 83.3%).

The synthetic route of 5744-80-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BUETTELMANN, Bernd; KOCER, Buelent; KUHN, Bernd; PRUNOTTO, Marco; RICHTER, Hans; RITTER, Martin; RUDOLPH, Markus; SATZ, Alexander Lee; (204 pag.)WO2017/5583; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 866837-96-9,Some common heterocyclic compound, 866837-96-9, name is Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate, molecular formula is C12H13N3O2, 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.

5-(3,3-Dimethyl-2-oxo-butylamino)-1 -phenyl-1 H-pyrazole-3-carboxylic acid ethyl ester; O,6g (25,9mmol) of 5-Amino-1 -phenyl-1 H-pyrazole-3-carboxylic acid ethyl ester are dissolved in 50ml DMF, 4,65g (25,9mmol) 1 -bromopinacolone and 16g (49.1 mmol, 1 ,9eq) of Cs2CO3 are added and the resulting mixture is heated to 100C for4hours.The reaction mixture is filtrated and the solvent removed in vacuo, the residue is subjected to preparative HPLC chromatography to obtain 2g (23%) of the product.

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-1-phenyl-1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; SANOFI; RUF, Sven; SADOWSKI, Thorsten; HORSTICK, Georg; SCHREUDER, Herman; BUNING, Christian; OLPP, Thomas; WIRTH, Klaus; WO2012/101199; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 95162-14-4, 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 95162-14-4 as follows.

Intermediate 12: Methyl [N- (TERT-BUTOXVCARBONYL)-4- (1-TRITYL-1H-PVRAZOL-4-VL)-L-PHENVLALANINATE] To a mixture of [BROMOPYRAZOLE] (11) (1. 0g, 2. [56MOL),] boronic acid (1) (0.7g, 2. [14MMOL),] and potassium carbonate (1.5g, 10. [7MMOL)] in degassed DME [(10ML)] was added [PDCI2 [DPPF]] (0.088g, [0.] [1MMOL).] The reaction mixture was then heated to [70C] under nitrogen for 24 hours. Solvent was then removed in vacuo, and the residue was partitioned between ethyl acetate and water. The organic portion was dried over sodium sulphate and solvent evaporated in vacuo to give the crude product. Purification via silica gel chromatography (ethyl acetate/petroleum ether 40-60 1: 4) gave the title compound (0.74g) LCMS RT 4.11 min, [[CPH3] + 243]

According to the analysis of related databases, 95162-14-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2003/104200; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1018446-95-1, 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. 1018446-95-1, name is tert-Butyl 4-amino-1H-pyrazole-1-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

1-(2-(2-(2-(1H-Pyrazol-4-ylamino)-5-chloropyrimidin-4-yI)ethyl)phenyl)cyclopropanecarboxamide (19) A solution of 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A14 (0.070 g, 0.21 mmol) and teit-butyl 4- amino-i H-pyrazole-1-carboxylate (0.11 g, 0.63 mmol) was stirred in MeOH : water (10:1 ratio, 4 mL) at 70 00 for 2 hours and then at 90 00 for 16 hours. The volatiles were removed in vacuo and the residue was purified by silica gel column chromatography (Combiflash Rf, 0-15% MeOH in DCM) to give the title compound 19 as a light yellow solid (0.015 g, 19%). 1H NMR (300 MHz, d6-DMSO) O 0.93- 1.02(m, 2H), 1.38- 1.49 (m, 2H), 3.04-3.16 (m, 4H), 6.03 (brs, 1H), 6.98 (brs, 1H), 7.18-7.39 (m, 4H), 7.48-7.72 (m, 1H), 7.79-8.00 (m, 1H), 8.37 (5, 1H), 9.62 (5, 1H). LCMS-C: rt 4.92 mm; m/z 383 [M+H].

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 4-amino-1H-pyrazole-1-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; FOITZIK, Richard Charles; MORROW, Benjamin Joseph; HEMLEY, Catherine Fae; LUNNISS, Gillian Elizabeth; CAMERINO, Michelle Ang; GANAME, Danny; STUPPLE, Paul Anthony; LESSENE, Romina; KERSTEN, Wilhelmus Johannes Antonius; HARVEY, Andrew John; HOLMES, Ian Peter; WO2014/26243; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1260243-04-6, A common heterocyclic compound, 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, molecular formula is C6H9N3O2, 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 solution of sodium ethoxide (520mg, 7.6mmol) in EtOH (20mL) were added ethyl 3- amino-lH-pyrazole-4-carboxylate (1 g, 6.45 mmol) and solid 1,3-dimethyluracil (1.35g, 9.68mmol), under a N2atmosphere. The reaction mixture was stirred at 90 C for 3 h then cooled to 0 C in ice-water bath. Amber precipitate was appeared. The resulting amber precipitate was filtered off and dissolved in water (25 mL) and then the resulting solution was neutralized with acetic acid. White solid was appeared, filtered and collected the solid, and then azeotroped to dryness by refluxing in toluene (100 mL) to give the title compound as a white solid (900 mg, 67%). H NMR (300 MHz, DMSO-Lambda): delta (ppm) 11.78 (brs, 1H), 8.58 (d, J = 8.0 Hz, 1H), 8.15 (s, 1H), 6.16 (d, J= 7.9 Hz, 1H), 4.28 (q, J= 7.0 Hz, 2H), 1.29 (t, J= 7.0 Hz, 3H).

The synthetic route of 1260243-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; LI, Minxiong; LI, Xiaobo; WO2015/73267; (2015); 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. 84547-84-2, name is 4-Bromo-1-methyl-1H-pyrazole-5-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 4-Bromo-1-methyl-1H-pyrazole-5-carboxylic acid

A mixture of 4-bromo- 1 -methyl- 1 H-pyrazole-5-carboxylic acid (5.0 g, 24.4 mmol) and BH3.THF (36.6 mL of a 1 M solution in THF, 36.6 mmol) in THF (50 mL) was stirred at 50 C for 2 days; at this point LCMS showed the completion of the reaction. The reaction was cooled to RT and cautiously quenched with aq. IN HC1 and stirred at RT for 1 h, after which the mixture was extracted with EtOAc (3 X 50 mL). The combined organic extracts were concentrated in vacuo. The residue was chromatographed (80 g Si02; continuous gradient from 0% to 100% EtOAc in hexanes, 25 min) to give the title compound (3.60 g, 18.9 mmol, 77 % yield) as a white solid. LCMS, [M+H]+ = 193.0.

The synthetic route of 84547-84-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; CHENG, Peter Tai Wah; WANG, Ying; (140 pag.)WO2019/126085; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, 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 37622-90-5, Computed Properties of C6H8N2O2

To a solution of NaH (1.08 g, 25.70 mmol) in THF (30 mL) at ambient temperature under nitrogen atmosphere was added a solution of ethyl 1H-pyrazole-4-carboxylate (3.00 g, 21.41 mmol) in THF (10 mL) and stirring was continued for I h. Then benzyl bromide (3.06 mL, 25.7 mmol) was added over the period of 15 mm and the reaction was stirred for 22 h. Thereaction mixture was cooled to 10 C diluted with aqueous NH4CI (100 mL) and extracted with ethyl acetate (2 x 80 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Redisep-120 g, 0-30% EtOAc/n-Hexane) to obtain Intermediate 45A (450 g, 88%) as a white solid. 1H NMR. (400 MHz, 1)MSO-d6) 6 ppm 1.23 – 1 .28 (m, 3 H),4.21 (q. J:::: 719 Hz, 2 H), 537 (s, 2 H), 7.25 – 738 (in, 5 H), 787 (s, 1 H), 8.46 (s, 1 H). LCMS Method-H): retention time 1.8 mm, [M±H] 2310.

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 4-pyrazolecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; PANDA, Manoranjan; YADAV, Navnath Dnyanoba; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (321 pag.)WO2018/93569; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics