Tag: M.W=0-100

Synthetic Route of 31230-17-8,Some common heterocyclic compound, 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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 suspension of NaH (220 mg, 5.50 mmol) in anhydrous THF (3.5 mL) was added a solutionof 3-amino-5-methyl-1H-pyrazole (500 mg, 5.00 mmol) in anhydrous THF (6.5 mL) at 0 °C under argon atmosphere. After stirring for 30 min, Boc2O (1.31 mL, 5.50 mmol) was added and stirred at rt for 5.5 h. After the completion of the reaction, the mixture was quenched with saturated aqueous NaHCO3 (100 mL) and extracted with CH2Cl2 (4 × 75 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated by rotary evaporation. Purification by column chromatography (1:1 ? 1:2 hexanes/EtOAc) yielded S1r(377 mg, 38percent) as a light brown solid and S1r’ (472 mg, 48percent) as 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 5-Methyl-1H-pyrazol-3-amine, its application will become more common.

Reference:
Article; Jeong, Yunkyung; Lee, Jooyeon; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 24; 9; (2016); p. 2114 – 2124;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

1453-58-3, Adding a certain compound to certain chemical reactions, such as: 1453-58-3, name is 3-Methylpyrazole, 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 1453-58-3.

Step 1 1-(4-Methoxy-phenyl)-3-methyl-1H-pyrazole: The title compound was prepared from 4-methoxyphenylboronic acid (1.85 g, 12.1 mmol), 3-methyl-1H-pyrazoles (0.5 g, 6.1 mmol) using the general procedure A with a yield of 30% (0.4 g); MS (APCI) m/z: 189 (M+1, 100).

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-Methylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; deCODE genetics ehf.; US2008/33013; (2008); 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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Quality Control of 1H-Pyrazole-4-carbaldehyde

Example 12 Production of alpha-(4-pyrazolyl)-N-t-butylnitrone To a suspension of 1,1-dimethylnitroethane (546.0 mg, 5.29 mmol) and zinc (515.5 mg, 7.89 mmol) in ethanol (3.0 ml) was added acetic acid (950.0 mg, 15.8 mmol) dropwise at 5° C. while stirring. The mixture was stirred at room temperature for 45 minutes. After cooling the mixture to 5° C. again, pyrazole-4-carbaldehyde (255.4 mg, 2.66 mmol) was added dropwise to the mixture while stirring and stirred at room temperature overnight. Zinc acetate in the mixture was filtered off and the filtrate was concentrated and purified by silica gel chromatography (chloroform/methanol=10/1). Yield: 226.3 mg(51percent) 1H-NMR(CDCl3) 1.60(s, 9H), 6.56(d, 1H, J=2.0 Hz), 7.64(d, 1H, J=2.0 Hz), 7.71(s, 1H), 8.43(brs, 1H)

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; Sumitomo Pharmaceuticals Co., Ltd.; US6194461; (2001); B1;,
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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

General procedure B for the synthesis of the final product lb from intermediate E or K In a sealed tube, the bromo-intermediate E or K (0.08 mmole), t-BuONa (0.16 mmole) and the amine (0.16 mmole) were charged. The tube was filled with Argon, dry toluene (1.0 ml) was added and the mixture was stirred for 2 min. Then Pd2(dba)3 (0.0024 mmole) and t-BuXphos (0.016 mmole) were added and the vial was flushed with Argon and stirred for 2 min. The reaction mixture was then heated at 100 °C for 18h. The mixture was concentrated in vacuo and purified by flash chromatography eluting with ethyl acetate/n-heptane. To a solution of the purified product in dichloromethane (0.5ml) was added TFA (0.4 mmole) and the mixture was stirred at room temperature for 30 min. The mixture was diluted with dichloromethane and the organic layer was washed with saturated aqueous NaHC03, dried and evaporated. The crude material was purified by chromatography on NH2-silica using dichloromethane to give the pure final product lb. In case of using intermediate E, the coupling product was deprotected using CF3COOH as described above to give the pure final product lb.Example 36(S)-2-Amino-6-[2-fluoro-5-(2-methyl-2H-pyrazol-3-ylamino)-phenyl]-3,5,5,6-tetramethyl- 5,6-dihydro-3H-pyrimidin-4-oneThe coupling of [(S)-4-(5-bromo-2-fluoro-phenyl)- 1,4,5, 5-tetramethyl-6-oxo- 1,4,5, 6- tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (intermediate E8) and 2-methyl-2H- pyrazol-3-ylamine according to procedure B followed by deprotection yielded the title compound as a pale brown waxy solid. MS (ESI): m/z = 359.2 [M+H]+.

According to the analysis of related databases, 1192-21-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; SIENA BIOTECH S.P.A; BANNER, David; GABELLIERI, Emanuele; GUBA, Wolfgang; HILPERT, Hans; HORNSPERGER, Benoit; HUMM, Roland; MAUSER, Harald; MAYWEG, Alexander, V.; NARQUIZIAN, Robert; PINARD, Emmanuel; ROGERS-EVANS, Mark; WOLTERING, Thomas; WOSTL, Wolfgang; WO2012/19966; (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. 288-13-1, name is 1H-Pyrazole, A new synthetic method of this compound is introduced below., name: 1H-Pyrazole

3.40 g (0.05 mol) of pyrazoleAnd 2.8g (0.05mol) powdered KOH were added to a 100mL three-necked flask,Add 10mLDMSO as a solvent, the mixture was stirred at 80 for 30min,Then 6.25 g (0.05 mol) of 2-bromoethanol was added (added to the flask in 30 mL intervals, three times)Continue stirring for 20 ~ 30h, cooled to room temperature,After filtration, 20 mL of chloroform was added and the solution was washed with water (5 × 20 mL)Rotary drying to give a colorless transparent liquid 1-ethylpyrazole (yield: 60 ~ 70%).

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; 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

Reference of 1453-58-3,Some common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, molecular formula is C4H6N2, 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.

Method B(a) 1 -Benzenesulfongammal-3 -methyrpyrazole A mixture of 3-methylpyrazole (5 g, 60.9 mmol), benzenesulfonyl chloride (8.55 mL, 67 mmol) and triethylamine (9.3 mL5 67 mmol) in acetonitrile was heated at reflux for 2 h5 allowed to cool and concentrated. EtOAc (300 mL) was added and the solution was filtered and concentrated to provide a solid residue which was crystallised from EtOAc to give the title compound as an off-white powder (Yield: 7.92 g5 58 percent).1H-NMR (DMSO-d6): delta 8.35 (d, IH)5 7.97-7.94 (m, 2H), 7.78 (tt, IH)5 7.66 (t, 2H), 6.43 (d, IH)5 2.17 (S5 3H).

The synthetic route of 1453-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOLIPOX AB; WO2007/51981; (2007); 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. 930-36-9, name is 1-Methylpyrazole, A new synthetic method of this compound is introduced below., Safety of 1-Methylpyrazole

N-methylpyrazole (1.0 g, 1 eq.) was dissolved in N,N-dimethylformamide (2.8 ml, 3 eq.), phosphorus oxychloride (1.3ml, 1.2 eq.) was added dropwise at 90 C over about 1 h. The mixture was reacted for another 2 h and then cooled. The reaction liquid was poured into iced water and adjusted with 10% aqueous sodium hydroxide solution to PH 4?5, extracted four times with dichloromethane, rinsed with water twice, and separated by column chromatography to give 600 mg product

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 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

Adding a certain compound to certain chemical reactions, such as: 288-13-1, name is 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 288-13-1, Recommanded Product: 1H-Pyrazole

To a solution of 3-bromopyridine (5 g, 0.031 mol) in 50 ml of acetonitrile were added pyrazole (2.6 g, 0.038 mol), Cs2CO3 (16.5 g, 0.050 mol), Cu2O (0.226 g, 0.0016 mol), and salicylaldoxime (0.867 g, 0.006 mol) under N2 atmosphere. The reaction mass was refluxed for 24 hrs at 80 C. The reaction mass was concentrated and the crude was purified by column chromatography using ethyl acetate and hexane (1:1) to afford the pyrazolyl pyridine as a dark brown liquid (2 g, 43%): 1H NMR (400 MHz, CDCl3) delta 8.99 (d, J=2.8 Hz, 1H), 8.48 (dd, J=4.8, 1.2 Hz, 1H), 8.11-8.08 (m, 1H), 7.99 (d, J=1.2 Hz, 1H), 7.78 (d, J=1.2 Hz, 1H), 7.38-7.35 (m, 1H), 6.53 (t, J=1.2 Hz, 1H); MS (m/z) 146 [M+1].

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: 69843-13-6, name is 1-Methyl-1H-pyrazol-4-amine, 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 69843-13-6, name: 1-Methyl-1H-pyrazol-4-amine

Step 4: Preparation of tert-butyl {3-[(5-cyano-2-[(1-methyl-1H-pyrazol-4-yl)amino]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]cyclobutyl}carbamate To a microwave reaction vial was added tert-butyl {3-[(2-chloro-5-cyano-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]cyclobutyl}carbamate (508 mg, 1.0 mmol), 1-methyl-1H-pyrazol-4-amine (110 mg, 1.1 mmol), 1,4-dioxane (10 mL), Cs2CO3 (670 mg, 2.1 mmol, 2 mol eq), Xantphos (62 mg, 0.1 mmol) and Pd2(dba)3 (94 mg, 0.1 mmol). The reaction vial was flushed with nitrogen, capped, stirred and heated to 140 C. in a Biotage microwave reactor for 1 hr and 45 min. The reaction was diluted with EtOAc (120 mL) and water (20 mL). The organic layer was separated, washed with water (20 mL), brine (10 mL), and dried over Na2SO4. After concentrating the extract to dryness, the product was purified via flash chromatography eluting with a gradient of 0%-60% EtOAc in heptanes to afford the title compound (480 mg, 84 yield) as a light yellow solid. 1:1 cis:trans mixture: 1H NMR (400 MHz, DMSO-d6) delta ppm 9.42 (s, 1H) 8.11 (s, 1H) 7.96 (br. s., 1H) 7.49-7.60 (m, 1H) 7.20-7.46 (m, 1H) 5.53 (br. s., 2H) 4.11-5.13 (m, 1H) 3.82 (s, 3H) 3.56 (t, J=7.55 Hz, 2H) 2.83 (d, J=6.80 Hz, 1H) 2.39-2.48 (m, 2H) 2.02-2.16 (m, 1H) 1.39 (d, J=5.54 Hz, 9H) 0.84 (t, J=8.06 Hz, 2H) -0.12 (br. s., 9H). m/z (APCI+) for C26H38N8O4Si 555.1 (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-pyrazol-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; Cheng, Hengmiao; Johnson, JR., Theodore Otto; Kath, John Charles; Liu, Kevin Kun-Chin; Lunney, Elizabeth Ann; Nagata, Asako; Nair, Sajiv Krishnan; Planken, Simon Paul; Sutton, Scott Channing; US2013/79324; (2013); 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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 31108-57-3

To a stirred solution of ethyl 2-((2-chloroethyl) amino)-2-phenylacetate (0.10 g, 0.413 mmol) in DMF (1 ml) was added K2C03 (0.114 g, 0.827 mmol) at 25 C. After stirring for 15 minutes, 1 /7-pyrazolc-4-carhonitrilc (0.046g, 0.496 mmol) was added at 25 C. The reaction mixture was heated at 60 C for 3 hours. Then the reaction mixture was poured into ice water (15 ml) and the product was extracted with ethyl acetate (2 x 30 ml). The combined organic layers were washed with brine (20 ml), dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford the title compound (0.050 g, 40%). LCMS: m/z = 299.76 [M+l].

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; CONSTELLATION PHARMACEUTICALS, INC.; WILSON, Jonathan, E.; BRUCELLE, Francois; LEVELL, Julian, R.; (153 pag.)WO2019/161162; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics