Tag: M.W:100-200

Application of 27258-33-9, 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 27258-33-9 as follows.

To a solution of 1 -methyl- lH-pyrazole-5-carbaldehyde (1.0 g, 9.09 mmol) in DMF (8 mL) was slowly added NBS (1.62 g, 9.09 mmol) in DMF (5 mL). The mixture was stirred for overnight at room temperature. 1 N NaOH (9.1 mL) was added and the solution was stirred for 10 min, diluted with water (100 mL), extracted with EtOAc (30 mL* 3), dried over MgS04, filtered and concentrated to afford an orange solid (1.57 g, 92%). LRMS m/z (M+H) 187.9 found, 188.0 required.

According to the analysis of related databases, 27258-33-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCCOMAS, Casey, C.; KUDUK, Scott, D.; REGER, Thomas, S.; WO2014/81619; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 1-Methyl-1H-pyrazole-4-carbaldehyde

Intermediate 69 (600mg, 1 eq.) was dissolved in tetrahydrofuran, and lithium aluminum hydride (210 mg, 1 eq.) was added under ice bath and the mixture was reacted at room temperature for 2 h. After completion of the reaction, 210 mul of water, 210 mul of 10percent aqueous sodium hydroxide solution, and 630 mul of water were successively added, followed by addition of anhydrous magnesium sulfate. The mixture was stirred for a while, filtered and evaporated to dryness to give 400 mg of an oil. MS (ESI): 113(M+H)

The synthetic route of 25016-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Institute Of Materia Medica Chinese Academy of Sciences; SHEN, Jianhua; WANG, Yiping; CHEN, Xinde; XU, Wenwei; WANG, Kai; (84 pag.)EP3239135; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 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. The solvent 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 asolid. The crude product was taken to the next step without further purification. MS calc?d [MHj 170.0, found 170.0.

The synthetic route of 5334-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIM, Jongwon; ALTMAN, Michael, D.; BRUBAKER, Jason, D.; GIBEAU, Craig, R.; (107 pag.)WO2016/144848; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2075-46-9, name is 4-Nitro-1H-pyrazole, 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 2075-46-9, Recommanded Product: 4-Nitro-1H-pyrazole

Into a 2 L three-necked round bottom flask affixed with an overhead stirrer, a temperature probe, an addition funnel, and a nitrogen inlet were added ethanol (600 mL) and 4-nitro-1H-pyrazole (50.6 g, 447 mmol). To this solution was added, in one portion, conc. HCl (368 mL) (note: rapid exotherm from 15 C. to 39 C.) and the resulting mixture was purged with nitrogen for 5 minutes. Palladium on alumina (5% w/w) (2.6 g, Alfa, black solid) was added to the mixture and stirred at room temperature while triethylsilane (208 g, 1789 mmol) was added drop-wise over 4 h. The reaction, which started to slowly exotherm from 35 C. to 55 C. over 2.0 h, was stirred for a total of 16 h and vacuum filtered through a plug of Celite to give a biphasic mixture. The mixture was transferred to a separatory funnel, the bottom aqueous layer was collected and rotary evaporated (60 C., 50 mmHg) to dryness with the aid of acetonitrile (3×350 mL). The resulting yellow solid was suspended in acetonitrile (150 mL) and allowed to stand for 2 h at room temperature followed by 1 h at 0 C. in the refrigerator. The solids were filtered and washed with acetonitrile (100 mL) to afford the titled compound 3-chloro-1H-pyrazol-4-amine hydrochloride (84 g, 97% yield, 80% purity) as a white solid: mp 190-193 C.; 1H NMR (400 MHz, DMSO-d6) delta 10.46-10.24 (bs, 2H), 8.03 (s, 0.54H), 7.75 (s, 0.46H), 5.95 (bs, 1H)); 13C-NMR (101 MHz, DMSO) delta 128.24, 125.97, 116.71.

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:
Patent; Dow Agrosciences LLC; Niyaz, Noormohamed M.; Garizi, Negar; Zhang, Yu; Trullinger, Tony K.; Hunter, Ricky; Buysse, Ann M.; Kubota, Asako; LePlae, Jr., Paul Renee; Knueppel, Daniel; Lowe, Christian T.; Pernich, Dan; Demeter, David A.; Johnson, Timothy C.; US2013/109566; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3994-50-1, name is 1-Methyl-4-nitro-1H-pyrazole, 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 3994-50-1, HPLC of Formula: C4H5N3O2

Example 1 7-(Azetidin-l-yl)-3-methyl-l-(l-methyl-5-(4-(trifluoromethyl)phenyl)-lH- pyrazol-4-yl)-lH-pyrazolo[4, -d]pyrimidine (a) 5-Chloro-l-methyl-4-nitro-lH-pyrazole Lithium bis(trimethylsilyl)amide (1.0 M, 65 mL, 65 mmol) in THF is added dropwise into a solution of l-methyl-4-nitro-lH-pyrazole (5.50 g, 43.3 mmol) and hexachloroethane (10.54 g, 44.5 mmol) in methylene chloride (120 mL) at 25 C. The reaction mixture is stirred at 25 C for 60 min, and then quenched with water (1 mL). The mixture is evaperated to dryness. The residue is washed with water (50 mL), sat. NaHCC>3 two times (2×30 mL) and brine (30 mL) successively, and then dried under vacuum to give 6.50 g of product (93% yield). MS (ESI) mJz 162.0 [M+H]+. NMR (500 MHz, CDC ) delta 8.15 (s, 1H), 3.92 (s, 3H).

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

Reference:
Patent; INTRA-CELLULAR THERAPIES, INC.; LI, Peng; ZHENG, Hailin; SNYDER, Gretchen; WENNOGLE, Lawrence P.; HENDRICK, Joseph; (28 pag.)WO2016/90380; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 127107-23-7, name is 1-Methyl-1H-pyrazol-4-amine hydrochloride, 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 127107-23-7, Safety of 1-Methyl-1H-pyrazol-4-amine hydrochloride

2-((6-((2,5-dichloropyrimidin-4-yl)amino)hexahydrofuro[3,2-b]furan-3-yl)oxy)ethanol (0.18 g, 0.54 mmol) was suspended in n-BuOH (5 mL) and 1-methylpyrazol-4-amine hydrochloride (0.15 g, 1.10 mmol) and N,N-diisopropylethylamine (0.28 g, 2.18 mmol) were added thereto. The mixture was placed in a sealed tube and then heated to 150 C with stirring overnight and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (DCM / MeOH (v / v) = 20/1). The title compound was obtained as a brown viscous liquid (42 mg, 20%).

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:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Li Xiaobo; Dai Weilong; Wang Tingjin; (74 pag.)CN104926824; (2017); B;,
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 78703-53-4 as follows. Safety of 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid

A mixture of tert-butyl [2-(3-chloro-5-fluorobenzyl)-4-methyl-1,3-thiazol-5-yl]carbamate (500 mg, 1.40 mmol) obtained in Example 145-E), concentrated hydrochloric acid (1 mL) and ethanol (2 mL) was stirred at 50C for 1 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in DMF (3 mL), 1,3-dimethyl-1H-pyrazole-4-carboxylic acid (216 mg, 1.54 mmol), HATU (585 mg, 1.54 mmol) and DIEA (0.12 mL, 0.70 mmol) were added, and the mixture was stirred at 60C for 4 hr. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography [eluent: ethyl acetate-methanol (100:0-80:20)]. The obtained solid was crystallized from heptane-ethyl acetate to give the title compound (40 mg) as a pale-brown solid (yield 8%). MS (ESI+): [M+H]+ 379. 1H NMR (300 MHz, CDCl3) delta 2.39 (3H, s), 2.55 (3H, s), 3.88 (3H, s), 4.18 (2H, s), 6.90-7.01 (2H, m), 7.08-7.12 (1H, m), 7.46 (1H, s), 7.81 (1H, s). mp 125-128C

According to the analysis of related databases, 78703-53-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2530078; (2012); 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. 13808-62-3, name is 4-Methyl-3-phenyl-1H-pyrazole, A new synthetic method of this compound is introduced below., COA of Formula: C10H10N2

General procedure: A mixture of (E)-2-methyl-3-phenylacrylaldehyde (1c) (146 mg, 1.0 mmol) and TsNHNH2 (205 mg, 1.1 mmol) in CH3CN (2 mL) were stirred at room temperature for 3 h and then CH3CN (2 mL), NaOH (44 mg, 1.1 mmol) were added and the mixture was heated at reflux for 15 h, then NaOH (60 mg, 1.5 mmol) and benzyl bromide (255 mg, 1.5 mmol) were subsequently added and the mixture was stirred at room temperature for 2 h. The product was extracted with Et2O and the organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. Purification by chromatography on silica gel afforded the desired product 4k as colorless oil (233 mg, 94%).

The synthetic route of 13808-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tang, Meng; Zhang, Fu-Min; Tetrahedron; vol. 69; 5; (2013); p. 1427 – 1433;,
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. 27006-76-4, name is 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H7ClN2O

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.

The synthetic route of 27006-76-4 has been constantly updated, and we look forward to future research findings.

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;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 112758-40-4,Some common heterocyclic compound, 112758-40-4, name is 3-Methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.

Preparation of 1-(2-chloropyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carbaldehyde; Intermediate 1 To a solution of ethyl 3-methyl-1H-pyrazole-4-carbaldehyde (6.4 g, 58.0 mmol) in 60 mL of anhydrous N,N-dimethylformamide were added potassium carbonate (10.8 g, 77.8 mmol) and 2,4-dichloropyrimidine (8.64 g, 58.0 mmol) at room temperature. The resulting suspension was stirred for 14 hours at room temperature with monitoring a reaction with LC-MS or thin layer chromatography (TLC). The reaction mixture was diluted with ethyl acetate and washed with brine (*2). The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting residue was purified by silica gel chromatography using a mixture of heptanes and ethyl acetate to afford the desired intermediate 1 as a white solid (5.47 g, 42%); MS (ESI) m/z 223 [M+H]+, 1H NMR (300 MHz, CDCl3) delta 10.06 (s, 1H), 9.04 (s, 1H), 8.70 (d, 1H, J=5.4 Hz), 7.87 (1H, d, J=5.4 Hz), 2.59 (s, 3H).

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

Reference:
Patent; Lee, Jaekyoo; Choi, Jang-Sik; Hwang, Hae-Jun; Song, Ho-Juhn; Kim, Jung-Ho; Kim, Se-Won; Koh, Jong Sung; Lee, Jaesang; Lee, Tae-Im; Choi, Yung-Geun; Park, Sung-Ho; Lee, In Yong; Suh, Byung-Chul; Salgaonkar, Paresh Devidas; Jung, Dong-Sik; US2015/111883; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics