Tag: M.W:200-300

Synthetic Route of 155600-99-0,Some common heterocyclic compound, 155600-99-0, name is 3,5-Dibromo-1-methyl-4-nitro-1H-pyrazole, molecular formula is C4H3Br2N3O2, 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.

Production example 7 3-bromo-5-(2′-hydroxyethylamino)-1-methyl-4-nitropyrazole 3 g (10.5 mmoles) of 3,5-dibromo-1-methyl-4-nitropyrazole are heated in a solution of 30 ml ethanolamine in 30 ml ethanol for 15 hours at boiling temperature. The reaction mixture is then poured on 200 ml water, the separated product is filtered, washed with water (20 ml) and vacuum dried. Additional product crystallizes from the filtrate when cooled (5 C.). 2.25 g (81 percent of theory) of 3-bromo-5-(2′-hydroxyethyl)amino-1-methyl-4-nitropyrazole are obtained in the form of yellow crystals with a melting point of 150 C. 1 H-NMR (60 MHz, DMSO-d6): =7.38 (s; wide; 1H; –NH; exchangeable with D2 O), 4.98 (s; wide; 1H; –OH; exchangeable with D2 O), 3.82 (s; 3H; N–CH3) and 3.60 ppm (m; 4H; –NH –CH2 –CH2). MS (70 eV):m/e=266 (M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dibromo-1-methyl-4-nitro-1H-pyrazole, its application will become more common.

Reference:
Patent; Wella Aktiengesellschat; US5663366; (1997); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1105039-93-7, A common heterocyclic compound, 1105039-93-7, name is 1-(4-Methoxybenzyl)-1H-pyrazole-4-carboxylic acid, molecular formula is C12H12N2O3, 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.

According to Scheme 3 Step 1: A solution of 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylic acid (34.4 mmol, 8.00 g), oxalyl chloride (68.9 mmol, 5.92 mL) and a drop of DMF in DCM (80 mL) was stirred for 1 hour at room temperature. After evaporation, the crude product was dissolved in DCM (30 mL) and was added at 0 C. to a solution of N,O-dimethylhydroxylamine hydrochloride (103 mmol, 6.31 g) in DCM (100 mL) followed by Et3N (138 mmol, 19.2 mL). The reaction mixture was stirred for 1 hour at room temperature. The reaction was quenched with a saturated solution of Na2CO3 (300 mL) and the aqueous phase was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was concentrated to yield N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide (33.8 mmol, 9.30 g, 98%) as a beige solid.LC (Zorbax SB-C18, 3.5 mum, 4.6×50 mm Column): RT=1.78 min; MS m/z ES+=276.

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; Bolea, Christelle; Calanire, Sylvain; US2010/144756; (2010); 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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

A solution of 4-iodo-1-methyl-1H-pyrazole (0.80 g, 3.9 mmol) in THF (7.04 g, 8.00 ml, 98 mmol) was cooled at 0 C. A solution of isopropylmagnesium chloride lithium chloride complex in THF (5.42 ml, 4.23 mmol, 0.78 molar) was added dropwise and the reaction was stifled for 1 hour. A solution of N-methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide (0.733 g, 4.23 mmol) in THF (2 mL) was added dropwise. Cooling was removed after 15 min and reaction was then stirred for 2 hours. To the mixture was added 2 M HCl (20 mL) and it was extracted with AcOEt (3×25 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography to yield (1-methyl-1H-pyrazol-4-yl)(tetrahydro-2H-pyran-4-yl)methanone (220 mg, 1.13 mmol, 29.4% yield). [0365] 1H NMR (600 MHz, CDCl3) delta 7.87 (s, 1H), 7.87 (s, 1H), 4.03 (ddd, J=11.4, 4.1, 2.4 Hz, 2H), 3.92 (s, 3H), 3.49 (td, J=11.7, 2.3 Hz, 211), 3.06 (tt, J=11.3, 3.8 Hz, 1H), 1.86 (dtd, J=13.8, 11.7, 4.4 Hz, 2H), 1.72 (ddd, J=13.4, 3.7, 2.0 Hz, 2H)

The synthetic route of 39806-90-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. Lundbeck A/S; Kilburn, John Paul; Rasmussen, Lars Kyhn; Jessing, Mikkel; Eldemenky, Eman Mohammed; Chen, Bin; Jiang, Yu; Hopper, Allen T.; US2014/107340; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 37687-24-4,Some common heterocyclic compound, 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, molecular formula is C9H12N2O4, 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.

In 250 mL of acetonitrile was dissolved 2-chloro-l-(l -methyl- 1H- pyrazol-4-yl)ethanone (18.3 g, 115 mmol) and diethyl lH-pyrazole-3,5-dicarboxylate (24.5 g, 115 mmol) before finely ground K2CO3 (31.9 g, 231 mmol) was added in one portion. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was filtered, and the cake was washed with acetonitrile (100 mL). The filtrate was concentrated in vacuo to a thick oil. The oil was dissolved in EtOAc (80 mL), and heptane (200 mL) was added slowly with stirring. The resultant solids were stirred for 2 h, then filtered and washed with heptane. The solids were dried in a vacuum oven to afford the title compound (26.4 g, 67% yield).

The synthetic route of 37687-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANDREWS, Steven W.; BLAKE, James F.; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MORENO, David A.; REN, Li; WALLS, Shane M.; (421 pag.)WO2018/136661; (2018); A1;,
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. 141573-95-7, name is Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

30.8g (0.151mol)3-Fluoroalkyl-1-methylpyrazole-4-carboxylic acid ethyl ester (DFMPA) was put into the reaction flask, 100 g of water, 6.7 g of sodium hydroxide were added, and the reaction was stirred at 70 C for 2 hours. After the reaction was completed, Add hydrochloric acid dropwise to neutralize to pH 2, cool to 10 C, filter, wash with a little cold water, and dry to obtain 3-fluoroalkyl-1-methyl-1H-pyrazole-4-carboxylic acid (DFMPA) (such as (Expression V) 25.2 g, 95% yield, 99% purity by HPLC.

According to the analysis of related databases, 141573-95-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Suqian Kelaibo Biochemical Co., Ltd.; Wang Mingchun; Li Qingyi; (11 pag.)CN110577503; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 657428-42-7, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-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. category: pyrazoles-derivatives

Intermediate 5; 2-(Methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole; Step A: tert-Butyl 1-(methylsulfonyl)]-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate (A) and tent-butyl 2-(methylsulfonyl)]-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate (B); A suspension of N-Boc-pyrazolopyrrolidine (Intermediate 3, Step B) (27.16 g, 130 mmol) in anhydrous acetonitrile (1.0 L) was charged in a 2.0 L three-neck flask fitted with a thermometer and an addition funnel and then treated with sodium hydride (60% dispersion in oil, 6.23 g, 156 mmol) while under nitrogen atmosphere in one portion. The reaction mixture was stirred at room temperature for 2 h. The resulting white suspension was then cooled in an ice bath and methanesulfonyl chloride (25.2 mL, 324 mmol) was slowly added via addition funnel The ice bath was then removed and the mixture was stirred 1 h at room temperature. The reaction mixture was quenched with water (500 mL) and the layers were separated. The aqueous layer was then extracted with 2×500 mL of dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to give a mixture of products A and B as colorless syrups. NMR in CD3OD indicated a 1:1 mixture of two products, in which the proton on the pyrazole ring in product A appeared at 7.70 ppm while the proton in product B appeared at 7.95 pm. LC-MS: 288.08 (M+1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 657428-42-7, its application will become more common.

Reference:
Patent; Biftu, Tesfaye; Chen, Ping; Cox, Jason M.; Weber, Ann E.; US2010/120863; (2010); 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. 1269293-48-2, name is Ethyl 5-bromo-1-methyl-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C7H9BrN2O2

Step 2b. A solution of compound form step 2a (400 mg, 1.44 mmol), 1,3,5-trichloro- l,3,5-triazinane-2,4,6-trione (700 mg, 3.14 mmol) in MeCN/AcOH/water 15ml (80/3/2) was stirred for 1 hour at -5C before was partitioned (EtOAc-brine). The organic was dried (Na2S04), filtered and concentrated to give the desired compound (500 mg) as a yellow oil. ESI-MS m/z =253.00 [M+H]+. This material was used directly in the next step without further purification.

The synthetic route of 1269293-48-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; QIU, Yao-ling; LI, Wei; CAO, Hui; JIN, Meizhong; GAO, Xuri; PENG, Xiaowen; KASS, Jorden; OR, Yat, Sun; (84 pag.)WO2016/183266; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 81190-89-8, 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. 81190-89-8, name is Methyl 4-bromo-1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

[1197] to a mixture of methyl 4-bromo-1H-pyrazole-3-carboxylate (15.0 g, 73.2 mmol,) andCs2CO3 (59.6 g, 182.9 mmol) in DMF(150 ml) was added mel (14.7 ml, 236.0 mmol) drop-wise at 0c under N2. The mixture was stirred at 25 C for 16 hours. The reaction mixture was filtered, the cake washed with ethyl acetate (200 ml x 2). The filtrate was washed with water (70 ml x 4) and the aqueous phase extracted with ethyl acetate (150 ml). The combined organic extracts were dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to dryness. The crude product which was purified by fcc (gradient eluent: petroleum ether/ethyl acetate from 100/0 to 50/50) to afford the title compound 240a (8.3 g, yield 51.8%) as a white solid and the title compound 240b (7.0 g, yield 43.7%) as white solid. Compound 240a: 1H NMR (400mhz, CDCl3): delta 7.48 (s, 1h), 4.15 (s, 3h), 3.93 (s, 3h). MS (ESI) m/z (M+H)+ 219.0.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-bromo-1H-pyrazole-3-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 916766-83-1, 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. 916766-83-1, name is 3-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of methyl1H-pyrrolo[3,2-b]pyridine-3-carboxylate (2.2 g, 12.50mmol), 3-[4-(chloromethyl)phenyl]-1-methyl-1H-pyrazole(3.04 g, 12.5 mmol), and KOH (1.4 g, 25.0 mmol) in acetone (80 mL) was stirredat 50 C for 18 h. The reaction mixture was concentrated, diluted with 100 mLof H2O, and neutralized to pH 7 with 6.0 M aq. HCl. The aq. mixture was extracted with EtOAc (2 x100 mL), and the combined extracts were dried (Na2CO3),filtered, and concentrated to afford 4.3 g (99%) of intermediate 7a as a yellow solid. Intermediate 7a was used in the following step without additional purification.

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, 3-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Davoren, Jennifer E.; O’Neil, Steven V.; Anderson, Dennis P.; Brodney, Michael A.; Chenard, Lois; Dlugolenski, Keith; Edgerton, Jeremy R.; Green, Michael; Garnsey, Michelle; Grimwood, Sarah; Harris, Anthony R.; Kauffman, Gregory W.; Lachapelle, Erik; Lazzaro, John T.; Lee, Che-Wah; Lotarski, Susan M.; Nason, Deane M.; Obach, R. Scott; Reinhart, Veronica; Salomon-Ferrer, Romelia; Steyn, Stefanus J.; Webb, Damien; Yan, Jiangli; Zhang, Lei; Bioorganic and Medicinal Chemistry Letters; vol. 26; 2; (2016); p. 650 – 655;,
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. 916766-83-1, name is 3-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 916766-83-1

To a mixture of 3- ( (3S, 4S) -4-hydroxytetrahydro-2H-pyran- 3-yl) -7-methyl-6- (4,4,5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl ) – 2H-benzo [e] [1, 3] oxazin-4 (3H) -one (0.10 g), 3-(4- (chloromethyl) phenyl) -1-methyl-lH-pyrazole (0.06 g) ,tetrakis (triphenylphosphine) alladium (0) (15 mg) , and DME (3 mL) was added 2 M aqueous sodium carbonate solution (0.26 mL) at room temperature, and the mixture was stirred under an argon atmosphere at 80C overnight. The reaction mixture was diluted with ethyl acetate, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethylacetate/hexane) and crystallized from ethyl acetate to give the title compound (0.05 g) .XH NMR (300 MHz, DMSO-d6) delta 1.33-1.64 (1H, m) , 1.81-1.96 (1H, m) , 2.24 (3H, s) , 3.31-3.50 (2H, m) , 3.64-3.73 (1H, m) , 3.75- 3.84 (1H, m) , 3.86 (3H, s) , 3.87-4.01 (4H, m) , 5.06 (1H, d, J = 5.3 Hz), 5.18-5.39 (2H, m) , 6.62 (1H, d, J = 2.3 Hz), 6.89 (1H, s), 7.14 (2H, d, J = 8.3 Hz), 7.54 (1H, s) , 7.65-7.73 (3H, m) .

According to the analysis of related databases, 916766-83-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; SUGIMOTO, Takahiro; SUZUKI, Shinkichi; SAKAMOTO, Hiroki; YAMADA, Masami; NAKAMURA, Minoru; KAMATA, Makoto; SHIMOKAWA, Kenichiro; OGINO, Masaki; KIMURA, Eiji; MURAKAMI, Masataka; YONEMORI, Jinichi; KOJIMA, Takuto; (281 pag.)WO2016/208775; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics