Tag: M.W:200-300

Electric Literature of 1280210-79-8,Some common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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.

4,6-Dihydro-2H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester (0.50 g, 2.39 mmol) was dissolved in tetrahydrofuran (15 mL).Nitrogen protection,Sodium hydride (0.19 g, 4.77 mmol, 60%) was added at 0 C, and the mixture was slowly warmed to room temperature for 1 hour.Cool down to 0 C,Thiophene-2-sulfonyl chloride (0.65 g, 3.58 mmol) was added and allowed to react at room temperature for 15 hours.The reaction was quenched with water (10 mL) EtOAc.The combined organic phases were washed with a saturated sodium chloride solution (10 mL).Dry over anhydrous sodium sulfate and concentrate by suction filtration.The residue was subjected to silica gel column chromatography[ethyl acetate/petroleum ether (v/v) = 1/4] purified,The title compound was obtained (0.71 g, 84%).It is a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ruyuan Yong Xing Technology Services Co., Ltd.; Li Jianhao; Gu Zheng; Deng Xinshan; Tang Wanjun; Zhang Zongyuan; Kang Panpan; Yuan Weihui; Peng Fei; (49 pag.)CN109942583; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 39806-90-1, 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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 4-Iodo-1-methyl-1H-pyrazole 1 (101 mg, 0.5 mmol) and phenylboronic 2 (59 mg, 0.5 mmol) were dissolved in DME (3 mL) and H2O (1.2 mL) in a microwave vial under a nitrogen atmosphere. Pd(PPh3)4 (2 mmol%, 11.6 mg) and Cs2CO3 (407.3 mg, 1.25 mmol) were added, and the reaction mixture was irradiated in a microwave apparatus at 90 C for 5-12 min. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by silica gel column chromatography using petroleum ether/acetone as eluent to give the title compound.

The synthetic route of 4-Iodo-1-methyl-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cheng, Hua; Wu, Qiong-You; Han, Fan; Yang, Guang-Fu; Chinese Chemical Letters; vol. 25; 5; (2014); p. 705 – 709;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 155377-19-8,Some common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, molecular formula is C7H7F3N2O2, 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 ethyl 3- {trifluoromethyl) -lH-pyrazole-4- carboxylate (0.208 g, 1.0 mmol) in DMF were added lH-indol-5- ylboronic acid (0.322 g, 2.00 mmol), Cu(OAc)2 (0.136 g, 0.75 rninol)/ and pyridine (0.162 ml, 2.00 mmol) and the mixture was stirred at room temperature for 3 days . The mixture was diluted with DCM and filtered through a pad of silica gel. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (3:1 hexanes/EtOAc) to give ethyl 1- (lH-indol-5-yl) -3- (trifluoromethyl) -lH-pyrazole-4- carboxylate (0.313 g, 97%) as a solid: 1H NMR (CDCl3) delta 1.39 (t, 3H7 J = 7.0 Hz), 4.37 Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/11131; (2008); A2;,
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. 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., Recommanded Product: 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

Electric Literature of 10250-64-3,Some common heterocyclic compound, 10250-64-3, name is 1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, molecular formula is C11H10N2O2, 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: To a solution of 19 (1.2 eq) and HOBt(1.4 eq) in DMF (0.5 M) were added EDCI (1.3 eq) and a solution of 15a-j or 16a-j (1.0 eq) in DMF (0.25 M), Et3N (3.5 eq) at 0 C. The reaction mixture was stirred at room temperature for 24 hours, then diluted in AcOEt. The organic phase was washed with water twice, saturated aqueous NaHCO3 three times, and brine, then dried over Na2SO4,filtered, and concentrated. The residue was purified by flash column chromatography to give intermediates 17a-j and 18a-j.

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

Reference:
Article; Nakagawa, Hidehiko; Seike, Suguru; Sugimoto, Masatoshi; Ieda, Naoya; Kawaguchi, Mitsuyasu; Suzuki, Takayoshi; Miyata, Naoki; Bioorganic and Medicinal Chemistry Letters; vol. 25; 23; (2015); p. 5619 – 5624;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 138907-68-3, A common heterocyclic compound, 138907-68-3, name is Ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate, molecular formula is C12H12FN3O2, 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.

General procedure: Intermediate 4 (0.001mol) and 5 (0.001mol) were dissolved in pyridine, phosphorus oxychloride is slowly added dropwise under ice bath conditions, then at 40-60C reacted for 5-8h. Finally, the mixture was poured into 30mL saturated Na2CO3 solution and stirred well. After the mixture was acidified, the saturated CuSO4 solution was used to remove pyridine, which greatly improved the purity and yield of the product. The data for compounds 8I-8VI are provided in the supporting information.

The synthetic route of 138907-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Hao; Ren, Zi-Li; Wang, Wei; Gong, Jie-Xiu; Chu, Ming-Jie; Ma, Quan-Wei; Wang, Jie-Chun; Lv, Xian-Hai; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 81 – 87;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, 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 345637-71-0, Computed Properties of C7H7F3N2O2

A mixture of 5-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2- thiazolyl]tetrahydro-2H-l,2-oxazine (i.e. the product of Step K) (0.235 g, 0.67 mmol), 5- methyl-3-(trifluoromethyl)-lH-pyrazole-l -acetic acid (0.154 g, 0.74 mmol) and N,N-dicyclohexylcarbodiimide (0.152 g, 0.74 mmol) in dichloromethane was stirred at room temperature for 20 h. The reaction mixture was diluted with more dichloromethane and the urea by-product was removed by filtration. The filtrate was concentrated under reduced pressure to a pale-yellow foam (0.42 g). The resulting foam was dissolved in a minimum amount of dichloromethane and loaded onto a chromatotron plate (2mm) eluting with a gradient of ethyl acetate in dichloromethane to give the title compound, a compound of the present invention, as a colourless foamy solid (0.101 g).in NMR (CDCI3): delta 2.05-2.20 (m, 1H), 2.20-2.35 (m, 4H), 3.403.55 (m, 1H), 3.55-3.70 (m, 2H), 3.75-3.88 (m, 1H), 4.08-4.20 (m, 1H), 4.35-4.45 (m, 1H), 4.45-4.55 (m, 1H), 5.08 (s, 2H), 6.02-6.12 (m, 1H), 6.30 (s, 1H), 6.85-6.98 (m, 2H), 7.25-7.38 (m, 1H), 7.72 (s, 1H).

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, 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; LIEPA, Andris, Juris; PASTERIS, Robert, James; STEVENSON, Thomas, Martin; WO2011/85170; (2011); 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 20055-01-0 as follows. Computed Properties of C4H10N4O4S

To a solution of (2S)-2- [ (BENZYLOXYCARBONYL) AMINO]-6- [ (TERT- butoxycarbonyl) amino] hexanoic acid (19.02 g) and triethylamine (5.56 g) in tetrahydrofuran (200 ml) was added methyl chloroformate (4.21 ml), followed by stirring under ice-cooling for 30 minutes. To the reaction mixture was added a solution of 1-METHYL-LH- pyrazole-4,5-diamine sulfate (15.75 g) and triethylamine (15.2 g) in water (50 ml) at the same temperature. The mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added chloroform (300 ml), and the layers were separated. The organic layer was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give a crude product of 1- benzyl 5-tert-butyl (lS)- {l- [ (5-amino-l-methyl-lH- pyrazol-4-yl) CARBAMOYL] PENTAMETHYLENE} biscarbamate as an oil. The crude product was used directly in the next step without further purification. To a solution of the crude product of 1-benzyl 5- tert-butyl (LS)-{1-[(5-AMINO-1-METHYL-LH-PYRAZOL-4- yl) CARBAMOYL] PENTAMETHYLENE} BISCARBAMATE IN. methanol (350 ml) was treated with 10% palladium on carbon (2.0 g) under a hydrogen atmosphere at room temperature for 6 days. After the catalyst was filtered off, the filtrate was concentrated in vacuo. The residue was triturated with ethyl acetate and dried in vacuo to give tert-butyl (5S)-5-amino-6- [ (5-amino-l-methyl-lH-pyrazol-4- yl) amino] -6-oxohexylcarbamate (12.1 g) as a solid. H-NMR (DMSO-D6) 6 1. 24-1. 40 (4H, m), 1. 36 (9H, s), 1. 70- 1.77 (2H, m), 2.88-2. 91 (2H, m), 3.51 (3H, s), 3.80-3. 82 (1H, m), 5.15 (2H, s), 6.77 (1H, br), 7.27 (1H, s), 10.05 (1H, br)

According to the analysis of related databases, 20055-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; Wakunaga Pharmaceutical Co., Ltd.; WO2005/27909; (2005); 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. name: 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

Electric Literature 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