Tag: M.W:100-200

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. 127107-23-7, name is 1-Methyl-1H-pyrazol-4-amine hydrochloride, A new synthetic method of this compound is introduced below., name: 1-Methyl-1H-pyrazol-4-amine hydrochloride

HATU (0.329 g, 0.867 mmol), DBU (0.152 g, 1.000 mmol) and 1- methyl-lH-pyrazol-4-amine hydrochloride (0.0745 mL, 0.800 mmol) were added to 6- bromoquinazolin-4(3H)-one (0.150 g, 0.667 mmol) in MeCN (3.5 mL). The solution was aged for 25 hours at ambient temperature before it was diluted with EtOAc and washed with brine-water. The concentrated organics were purified via silica gel chromatography eluting with 2% MeOH-EtOAc to yield 6-bromo-3-(l-methyl-lH-pyrazol-4-yl)quinazolin-4(3H)-one (0.018 g, 0.059 mmol, 18% yield).

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; ARRAY BIOPHARMA INC.; GENENTECH, INC.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MATHIEU, Simon; MORENO, David; REN, Li; RUDOLPH, Joachim; WENGLOWSKY, Steven Mark; WO2012/118492; (2012); A1;,
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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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., Safety of 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Example 6 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid chloride 3-(difluoromethyl)-1-methyl-1H-pyrazol-4-carboxylic acid obtained by example 5 is treated with oxalyl chloride (1,25 eq) in toluene, and a few drops of dimethylformamide are added. The mixture is concentrated under reduced pressure to yield the carboxyl chloride.

The synthetic route of 176969-34-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SOLVAY SA; JAUNZEMS, Janis; (39 pag.)WO2019/122164; (2019); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

Related Products of 175137-46-9,Some common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, molecular formula is C6H9N3, 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 2,4,6-trichloropyrimidine (Alfa, 12.25 g, 66.8 mmol), 3-amino-5- cyclopropyl-lH-pyrazole (Fluorochem 8.23 g, 66.8 mmol) and triethylamine (11.2 mL, 80.4 mmol) in ethanol (100 mL) was stirred at room temperature for 16 hours under Ar (balloon). The solvent was removed in vacuo and the crude material was dissolved in ethyl acetate. The solution was washed with water and dried (Na2S04), filtered and evaporated to give a beige solid. Pure product was obtained as a white crystalline solid afterrecrystallisation from acetonitrile. It was possible to obtain a second crop. From two runs performed under the same conditions, 29.0 g (88%) of 2,6-dichloro-N-(5-cyclopropyl-lH- pyrazol-3-yl)pyrimidin-4-amine. The product contained -10 % acetonitrile but was carried through to the next step regardless.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BANDYOPADHYAY, Deepak; EIDAM, Patrick M.; GOUGH, Peter J.; HARRIS, Philip Anthony; JEONG, Jae U.; KANG, Jianxing; KING, Bryan Wayne; LAKDAWALA SHAH, Ami; MARQUIS, JR., Robert W.; LEISTER, Lara Kathryn; RAHMAN, Attiq; RAMANJULU, Joshi M.; SEHON, Clark A; SINGHAUS, JR., Robert; ZHANG, Daohua; WO2014/125444; (2014); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 288148-34-5, name is 1-Methyl-1H-pyrazole-4-sulfonyl chloride, 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 288148-34-5, Recommanded Product: 1-Methyl-1H-pyrazole-4-sulfonyl chloride

The previous product (200 mg, 0.59 mmol) was dissolved in dichloromethane (5 mL). N1N- Diisopropylethylamine (0.15 mL, 0.88 mmol) was added followed by 1 -methyl- lH-pyrazole-4-sulfonyl chloride (116 mg, 0.64 mmol). The mixture was stirred for 2 hours at room temperature then purified directly by flash column chromatography on silica gel using a 20 % ethyl acetate : 80 % dichloromethane mixture as eluent to afford the title compound(160 mg).1H NMR delta (ppm)(CDCl3): 7.75 (1 H, s), 7.73 (IH, s), 7.61 (1 H, d, J = 8.3 Hz), 7.43 (1 H, d, J = 1.8 Hz), 7.33 (1 H, dd, J = 1.9, 8.3 Hz), 6.26 (1 H, m), 3.98 (3 H, s), 3.48 (2 H, d, J = 6.4 Hz), 3.22-3.18 (2 H, m), 3.02-2.96 (2 H, m), 1.74-1.67 (4 H, m), 1.27-1.25 (2 H, m), 0.67-0.61 (1 H, m), 0.52 (2 H, m), 0.05 (2 H, m). m/z (ES+) 485 (M+H).

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-Methyl-1H-pyrazole-4-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2006/67529; (2006); 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. 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 5334-40-7

Step 1: Into a 250 mL round bottom flask containing a suspension of 4-nitro-1H-pyrazole-3- carboxylic acid (20.0 g, 127 mmol) in methanol (100 mL) was added concentrated sulfuric acid (4 mL) dropwise over 5 mm at 0 C and the resulting slurry was refluxed at 80 C for 16 h. Thesolvent was removed under reduced pressure and the residual mass was dissolved in ethyl acetate (300 mL) and washed with saturated aqueous sodium bicarbonate solution (2 x 100 mL) and brine (100 mL) and dried over anhydrous sodium sulfate. The solution was filtered and concentrated under reduced pressure to give methyl 4-nitro-1H-pyrazole-3-carboxylate as a solid. The crude product was taken to the next step without further purification. MS calc?d [M5 Hj 170.0, found 170.0.

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; MERCK SHARP & DOHME CORP.; LIM, Jongwon; ALTMAN, Michael, D.; BRUBAKER, Jason, D.; GIBEAU, Craig, R.; (187 pag.)WO2016/144846; (2016); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5203-77-0, name is 1,3-Dimethyl-1H-pyrazol-5-ol, 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 5203-77-0, Quality Control of 1,3-Dimethyl-1H-pyrazol-5-ol

General procedure: Intermediate 7 (4mmol), dissolved in dry dichloromethane (60mL), and PCl5 (4.2mmol) were added and stirred at room temperature for 1h. The solvent was moved out under reduced pressure to afford acid chloride, the acid chloride was then dissolved in dry CH2Cl2 (60mL), Then 1-methyl-1H-pyrazol-5-ol (4mmol) and Et3N (4.8mmol) were added to the above solution, and stirred for a further 18-24hat room temperature. After adding dichloromethane (30mL), the resultant mixture was washed sequentially with 2N hydrochloric acid (100mL), saturated NaHCO3 and saturated NaCl and dried over Na2SO4. The rest of the solution was evaporated in vacuum and purified by silica gel column chromatography using gradient elution of ethyl acetate/hexane (V:V = 1:2) to obtain the desired intermediate 8 as a write powder (30%-70%). 4.1.10 1-methyl-1H-pyrazol-5-yl3-methyl-2-oxo-1-propyl-2,3-dihydro-1H-benzo[d] imidazole- 5-carboxylate Yield: 45%. m.p. 107-108C. 1H NMR (600MHz, CDCl3) delta 8.01 (dd, J=8.4, 1.2Hz, 1H), 7.77 (d, J=1.2Hz, 1H), 7.48 (d, J=1.8Hz, 1H), 7.10 (d, J=8.4Hz, 1H), 6.20 (d, J=1.8Hz, 1H), 3.92 (t, J=7.2Hz, 2H), 3.80 (s, 3H), 3.51 (s, 3H), 1.91-1.71 (m, 2H), 1.00 (t, J=7.8Hz, 3H). EI-MS (m/z): 314.18 (M)+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Xu, Yu-Ling; Lin, Hong-Yan; Ruan, Xu; Yang, Sheng-Gang; Hao, Ge-Fei; Yang, Wen-Chao; Yang, Guang-Fu; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 427 – 438;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 27006-76-4, The chemical industry reduces the impact on the environment during synthesis 27006-76-4, name is 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde, I believe this compound will play a more active role in future production and life.

General procedure: Toa stirred solution of substituted phenol (75 mmol) in DMF or DMSO (25mL), wasadded solid potassium hydroxide (90 mmol) at room temperature. The resultingmixture was stirred at 45 Cfor 2 h and then 5-chloropyrazole-4-carbaldehyde (5) (50 mmol) was added in portions. The reaction mixture was heatedto 110C. After6-22 h, the mixture was poured into water and extracted with ethyl acetate. Thecombined extracts were dried over anhydrous magnesium sulfate, filtered, andconcentrated to obtain compounds 6a-6z. Then the product 6 (10mmol) was added into a stirred mixture of hydroxylamine hydrochloride(15 mmol) and potassium hydroxide (20 mmol) in methanol or ethanol (30 mL) atthe room temperature. The reaction mixture was refluxed for 5-20 h. Oncompletion, the mixture was poured into water (80 mL), and the solidprecipitate was filtered, washed with water, and dried to afford thecorresponding pyrazole oximes 7a-7z, which were used for the following transformations withoutfurther 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, 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dai, Hong; Li, Gang; Chen, Jia; Shi, Yujun; Ge, Shushan; Fan, Chongguang; He, Haibing; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3818 – 3821;,
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Pyrazoles – an overview | ScienceDirect Topics

Reference of 1572-10-7, The chemical industry reduces the impact on the environment during synthesis 1572-10-7, name is 3-Amino-5-phenylpyrazole, I believe this compound will play a more active role in future production and life.

General procedure: The general method was described for the synthesis of D1. Compound C1 (150 mg, 0.393 mmol) was dissolved in ethanol (2 mL),followed by addition of 5-phenyl-1H-pyrazol-3-amine (62.63 mg, 0.393 mmol) and triethylamine (119.43 mg, 1.18 mmol). The mixture was stirred at room temperature for 5 h. The resultant mixture was purified by column chromatography to give D1.

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-Amino-5-phenylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Shuai; Shen, Dandan; Zhao, Lijie; Yuan, Xiaohan; Cheng, Jialing; Yu, Bin; Zheng, Yichao; Liu, Hongmin; Chinese Chemical Letters; vol. 31; 2; (2020); p. 418 – 422;,
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Reference of 7119-95-1, 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. 7119-95-1, name is 1-Nitropyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1-Nitropyrazole (1 g) was slowly added to a round-bottomed flask containing H2SO4 (98percent, 5 mL) and stirred for 20 h at room temperature. The reaction mixture was slowly transferred to a beaker containing ice with stirring. The solution was extracted with ether. The organic layer was dried with Na2SO4 then evaporated to afford 4-nitropyrazole as a colorless solid (0.97 g, 96percent). The solid was recrystallized from ether/hexane to get white crystalline compound. m.p. 163?165 °C; FT-IR (KBr, cm?1) 3186 (N?H), 1526 and 1353 cm?1 (NO2). 1H NMR (DMSO-d6) delta: 8.26 (d, 1, 5-H), 6.76 (d, 1, 3-H). EI-MS: m/z 113 (M+·). Anal. Calcd for C3H3N3O2: C, 27.54; H, 3.88; N, 32.42. Found: C, 28.31; H, 3.21; N, 31.38.

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

Reference:
Article; Nageswara Rao; Ravi; Tewari, Surya P.; Venugopal Rao; Journal of Molecular Structure; vol. 1043; (2013); p. 121 – 131;,
Pyrazole – Wikipedia,
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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. 146941-72-2, name is 4-Bromo-1-methyl-1H-pyrazol-3-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 4-Bromo-1-methyl-1H-pyrazol-3-amine

Example 0690 0690-1 A mixture of 4-bromo-1-methyl-1H-pyrazole-3-amine (150 mg), pyridine (2 mL), acetic anhydride (241 muL), and N,N-dimethylpyridine-4-amine (11 mg) was stirred at room temperature for 3 hours. The solvent was distilled off under reduced pressure, and methanol (3 mL) and a 20% sodium hydroxide aqueous solution (1 mL) were added to the obtained residue, followed by stirring at room temperature for 3 hours. After water and ethyl acetate were added to the reaction mixture, the organic layer was collected by separation, washed with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate-methanol), thereby obtaining N-(4-bromo-1-methyl-1H-pyrazol-3-yl)acetamide (79 mg). MS m/z (M+H): 218.

The synthetic route of 146941-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics