Category: pyrazoles-derivatives

Reference of 5952-93-2, These common heterocyclic compound, 5952-93-2, name is Methyl 1-methyl-1H-pyrazole-4-carboxylate, 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 stirred solution of LDA (2.0 M in THF) (10.7 mL, 21.42 mmol) in THF (10.0 mL) was added methyl 1-methyl- 1H-pyrazole-4-carboxylate (1.0 g, 7.14 mmol) in THF (10.0 mL) at -78 C slowly and stirred for 2 h. Dimethylformamide (2.5 mL, 32.84 mmol) was added to the reaction mixture at -78C and then allowed to stir at 0 C for 2 h. The reaction mixture was quenched with aqueous 1 M HC1 solution (10 mL) and extracted with EtOAc (3 x 10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Crude product was purified with silica gel chromatography using20% EtOAc / petroleum ether to afford 0.200 g of methyl 5-formyl-i-methyl-1H-pyrazole-4- carboxylate as pale yellow solid.?H NMR (400 MHz, CDC13) oe ppm 3.91 (s, 3H), 4.20 (s, 3H), 7.91 (s, 1H), 10.50 (s, 1H).

The synthetic route of 5952-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORION CORPORATION; HAIKARAINEN, Anssi; KUMPULAINEN, Esa; POHJAKALLIO, Antti; PYSTYNEN, Jarmo; WANG, Shouming; (191 pag.)WO2018/2437; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 107862-65-7, The chemical industry reduces the impact on the environment during synthesis 107862-65-7, name is 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole, I believe this compound will play a more active role in future production and life.

Step 8: Bromine (22.4 mL, 435 mmol) was added to a solution of 5,6-dihydro-4H- pyrrolo[l,2-b]pyrazole 8 (47.2 g, 437 mmol) and NaOAc (36.2 g, 440 mmol) in AcOH (750 mL) o drop wise at 0 C. The mixture was stirred at the same temperature for 10 minutes then neutralized by the addition of aqueous sodium bicarbonate. The aqueous layer was extracted with EtOAc (5 x 200 mL) and the organic extracts were dried over magnesium sulfate and concentrated under reduced pressure to afford 3-bromo-5,6-dihydro-4H-pyrrolo[l,2-b]pyrazole (73.5 g).

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, 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; MACHACEK, Michele, R.; ALTMAN, Michael, D.; ROMEO, Eric, T.; VITHARANA, Dilrukshi; CASH, Brandon; SIU, Tony; ZHOU, Hua; CHRISTOPHER, Matthew; KATTAR, Solomon, D.; HAIDLE, Andrew, M.; CHILDERS, Kaleen Konrad; MADDESS, Matthew, L.; REUTERSHAN, Michael, H.; DUCHARME, Yves; GUERIN, David. J.; SPENCER, Kerrie; BEAULIEU, Christian; TRUONG, Vouy Linh; GUAY, Daniel; NORTHRUP, Alan, B.; TAOKA, Brandon, M.; LIM, Jongwon; FISCHER, Christian; BUTCHER, John, W.; OTTE, Ryan, D.; SUN, Binyuan; WO2013/192125; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 947763-34-0, name is 1-Ethyl-3-methyl-1H-pyrazol-4-amine, molecular formula is C6H11N3, 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. Product Details of 947763-34-0

To a solution of 2,4-dichloro-1,3,5-triazine (330 mg, 2.2 mmol) in dichloromethane (15 mL) at 0 C., 1-ethyl-3-methyl-1H-pyrazol-4-amine (250.34 mg, 2 mmol) was added, followed by N,N-Diisopropylethylamine (0.523 mL, 3 mmol). The reaction mixture was stirred at 0 C. for 40 minutes. After this time, the reaction was quenched with saturated sodium bicarbonate solution (PH?8) and extracted with dichloromethane for three times. The combined extracts were washed once with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography (silica gel) to give the desired product as red solid. LCMS-ESI+ (m/z): [M+H]+ calcd for C9H12ClN6: 239.7. found: 239.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 947763-34-0, its application will become more common.

Reference:
Patent; Gilead Sciences, Inc.; Du, Zhimin; Guerrero, Juan A.; Kaplan, Joshua A.; Knox, JR., John E.; Lo, Jennifer R.; Mitchell, Scott A.; Naduthambi, Devan; Phillips, Barton W.; Venkataramani, Chandrasekar; Wang, Peiyuan; Watkins, William J.; Zhao, Zhongdong; (593 pag.)US2016/96827; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 52096-24-9, These common heterocyclic compound, 52096-24-9, name is 1-Butyl-1H-pyrazole, 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.

3.102 g (18 mmol) of hydrobromic acid was gradually added dropwise to 1.86 g (15 mmol) of 1-butylpyrazole,The reaction was stirred at 40 ~ 50 for 15 ~ 25h to ensure that all the substrates reacted completely, then cyclohexane was used as a water-carrying agent to remove the moisture therein,Further washing with ethyl acetate gave 1-butylpyrazole hydrobromide as a light yellow liquid (yield> 90%).

Statistics shows that 1-Butyl-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 52096-24-9.

Reference:
Patent; Henan University; Ren Tiegang; Wang Tengfei; Ma Yuan; Zhang Jingshun; Zhang Jinglai; Wang Li; (9 pag.)CN107501181; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 75092-25-0, name is Methyl 4-iodo-1-methyl-1H-pyrazole-3-carboxylate, 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 75092-25-0, Product Details of 75092-25-0

5.1.51 Methyl 1-methyl-4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-1H-pyrazole-3-carboxylate (36) To a mixture of 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one (34, 2.3 g, 9.78 mmol) and methyl 4-iodo-1-methyl-1H-pyrazole-3-carboxylate (35, 1.25 g, 4.70 mmol) in DMF (40 mL) and water (10 mL) were added Pd(PPh3)4 (814 mg, 0.71 mmol) and Cs2CO3 (3.06 g, 9.40 mmol), and the mixture was stirred at 80 C for 12 h. The mixture was concentrated in vacuo, and the residue was purified by silica gel column chromatography (0-5% MeOH in CHCl3) to give 36 (812 mg, 70%) as colorless solid. 1H NMR (DMSO-d6) delta 3.44 (s, 3H), 3.74 (s, 3H), 3.91 (s, 3H), 6.39 (d, 1H, J = 9.3 Hz), 7.51 (dd, 1H, J = 9.4, 2.6 Hz), 7.86 (d, 1H, J = 2.6 Hz), 7.94 (s, 1H); MS (ESI) m/z 248 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-iodo-1-methyl-1H-pyrazole-3-carboxylate, and friends who are interested can also refer to it.

Reference:
Article; Hamaguchi, Wataru; Masuda, Naoyuki; Miyamoto, Satoshi; Shiina, Yasuhiro; Kikuchi, Shigetoshi; Mihara, Takuma; Moriguchi, Hiroyuki; Fushiki, Hiroshi; Murakami, Yoshihiro; Amano, Yasushi; Honbou, Kazuya; Hattori, Kouji; Bioorganic and Medicinal Chemistry; vol. 23; 2; (2015); p. 297 – 313;,
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. 27511-79-1, name is 3-Amino-1H-pyrazole-4-carboxamide sulfate(2:1), This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H14N8O6S

This embodiment relates to a process for synthesizing a pyrazolo [3,4-d] pyrimidine compound, which comprises the following steps:Step one, 15 g of 3-aminopyrazole-4-carboxamide hemisulfateAnd 150g of formamide (molar ratio of 1:10) was added to a 100mL three-necked round bottom flask, first with hydrochloric acid to adjust the pH to 2.6, and then warmed to 115 , and stirred at this temperature for 12h at room temperature, the reaction mixture First clear as a clear solution and then gradually precipitated a white solid, the reaction was cooled to room temperature after the reaction;Step two, the product obtained in step one was placed in the range of 7 12h,Let the product fully crystallized from formamide solution;Step three, the filter, the filtrate recovery applied, the resulting crystal crude beaker into the beater by mass than the crude product: purified water ratio of 1:14 by adding purified water, beating washing 3 hours;Step four, filtered again, the filtrate was discarded, the filter cake was washed with purified water until the eluate pH ? 6, after drying to obtain a white 4-hydroxypyrazolo [3,4-d] pyrimidine, the state is white Crystal powder, molar yield of 92.1%, purity of 99.8%

According to the analysis of related databases, 27511-79-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Titan Technology Co., Ltd.; Xie Yingbo; Zhang Qing; Zhang Hua; Xu Xiaobing; Zhang Weiyan; Luo Guiyun; (6 pag.)CN104447758; (2017); B;,
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. 51516-68-8, name is 5-Amino-1-(3-chlorophenyl)-1H-pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H7ClN4

Title compound 2A, 5-amino-1-(3-chloro-phenyl)-1H pyrazole-4-carbonitrile (0.2 g, 0.91 mmol) was suspended in formamide (10 ml). The suspension was heated to 210C for 1 hour then allowed to cool to room temperature. To the reaction mixture was added water (10 ml), the resultant precipitate was collected by filtration, washed with water (2 x 10 ml) and dried on the filter. The crude solid was then purified by column chromatography with ethyl acetate/heptane (1: 1) as the eluent to give the title compound as a white solid (68 mg, 0.278 mmol, 30%). LC-MS: [M+H]+=246, Rt = 1.06 min, 98% purity.

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 51516-68-8.

Reference:
Patent; DeveloGen Aktiengesellschaft; Evotec AG; EP1746099; (2007); 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. 19959-77-4, name is 2-(5-Methyl-1H-pyrazol-3-yl)pyridine, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

To a solution of 2-(5-methyl-1H-pyrazol-3-yl)pyridine (27.9 g, 175 mmol) in carbon tetrachloride (300 mL) and dicholoromethane (300 mL) in a round-bottom flask was added N-bromosuccunimide (31.2 g, 175 mmol). The resulting mixture was stirred at room temperature for 21 hours and the reaction mixture was added water. The resulting solution was extracted with dicholomethane. The organic extracts were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting solid was washed with hexane/AcOEt (v/v =10/1) and dried under reduced pressure at 50 C. The title compound was obtained as a white solid. (37.5 g, 158 mmol, 90% yield): 1H NMR (400 MHz, CDCl3) d 8.61 (d, J = 3.1 Hz, 1H), 8.28 (d, J = 7.8 Hz, 1H), 7.80 (t, J = 7.8 Hz, 1H), 7.28 (t, J = 7.8 Hz, 1H), 2.34 (s, 3H).

According to the analysis of related databases, 19959-77-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Fukuda, Takeshi; Goto, Riki; Kiho, Toshihiro; Ueda, Kenjiro; Muramatsu, Sumie; Hashimoto, Masami; Aki, Anri; Watanabe, Kengo; Tanaka, Naoki; Bioorganic and Medicinal Chemistry Letters; vol. 27; 16; (2017); p. 3716 – 3722;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 96450-53-2, 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. 96450-53-2, name is 1-(2-Chloroethyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

As shown in step 20-i of Scheme 20, 2-(5,6-dimethoxypyridin-3-yl)-6-(lH- pyrazol-4-yl)-6,7-dihydro-5H-pyrrolo[3,4-¾]pyridin-5-one [Compound 70, 100 mg, 0.2964 mmol, prepared from 2-chloro-6-(lH-pyrazol-4-yl)-6,7-dihydro-5H-pyrrolo[3,4-¾]pyridin-5- one and 2,3-dimethoxy-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (Compound 2021) in a manner similar to the preparation of compound 135 as shown in Example 12], and cesium carbonate (193 mg, 0.593 mmol), were weighed into a conical microwave vial equipped with a stir bar. DMF (1.05 mL) was added followed by the addition of l-(2- chloroethyl)pyrazole ( 77 mg, 0.593 mmols). The vial was sealed and heated at 120C for 15 minutes. Water (3 mL) was added and the resulting precipitate collected by filtration and washed with 5 mL of water. The filtrate was concentrated under reduced pressure. Each of the collected solid and the residue from concentration of the filtrate was diluted with DMSO until solubilized and purified by reversed-phase HPLC to give 6-(l-(2-(lH-pyrazol-l- yl)ethyl)-lH-pyrazol-4-yl)-2-(5,6-dimethoxypyridin-3-yl)-6,7-dihydro-5H-pyrrolo[3,4- 6]pyridin-5-one (Compound 171, 22 mg, 0.05 mmol, 17% yield): ESMS (Mu+Eta) 432.0; 1H NMR (DMSO-de, 300 MHz) delta 8.47 (d, J = 2.0 Hz, 1H), 8.10 (s, 2H), 7.95-7.87 (m, 2H), 7.75 (s, 1H), 7.45 (d, J = 2.2Hz, 1H), 7.40 (d, J = 1.3 Hz, 1H), 6.12 (t, J = 2.0 Hz, 1H), 4.84 (s, 2H), 4.50 (s, 4H), 3.88 (s, 3H), 3.85 (s, 3H).

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, 1-(2-Chloroethyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; ARONOV, Alex; COME, Jon, H.; DAVIES, Robert, J.; PIERCE, Albert, C.; WANG, Jian; NANTHAKUMAR, Suganthini; CAO, Jingrong; BANDARAGE, Upul, K.; KRUEGER, Elaine; TIRAN, Amaud, Le; LIAO, Yusheng; MESSERSMITH, David; COLLIER, Philip, N.; GREY, Ronald; O’DOWD, Hardwin; HENDERSON, James, A.; GRILLOT, Anne-Laure; WO2011/87776; (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 113808-86-9 as follows. Computed Properties of C6H8N2O2

Example 139: 5-[4-(3,5-Dimethyl-1 H-pyrazole-4-carbonyl)-piperazin-1 -ylmethyl]- thiophene-2-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide trifluoroacetate To a solution of 3,5-dimethyl-1 H-pyrazole-4-carboxylic acid (18 mg, 0.13 mmol), HOBt*H2O (0.13 mmol), N-Methylmorpholine (1 mmol), 4-Dimethylaminopyridine (0.01 mmol) in 0.75 ml_ of DMF, a solution of intermediate 5 (0.1 1 mmol in 1 ml_ DMF) was added followed by EDC (neat, 0.13 mmol). The tube was closed with a screw cap and shaken over night at 40 C. 0.1 ml TFA was added and the volume was adjusted to 2.2 ml with DMF. The solution was filtered and submitted to preparative RP-HPLC purification to give 5-[4-(3,5-Dimethyl-1 H-pyrazole-4-carbonyl)-piperazin-1 -ylmethyl]- thiophene-2-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide trifluoroacetate as a colorless film (33 mg, 52%). 1 H NMR (DMSO-d6, 500 MHz) d ppm 9.22 (t, 1 H), 8.1 (d, 1 H), 7.80 (d, 1 H), 7.30 (bs, 1 H), 6.90 (d, 1 H), 6.69 (s, 1 H), 4.6 (bs, 2H), 4.40 (bs, 2H), 4.3-3.7 (broad signal, 4H), 3.7 (s, 3H), 3.5-3.0 (broad signal, 4H), 2.13 (s, 6H). LC/MS (Method 3); Rt = 1 .15 min; detected mass: m/z = 469.31 ([M+H]+)

According to the analysis of related databases, 113808-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI; MENDEZ-PEREZ, Maria; BREITSCHOPF, Kristin; LORENZ, Katrin; STROBEL, Hartmut; WANG, Li-hsing; SCHIFFER, Alexander; GOERLITZER, Jochen; WO2015/82474; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics