Day: June 18, 2021

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

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

Related Products of 31230-17-8, A common heterocyclic compound, 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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.

Method 8; 2-Chloro-5-fluoro-N-(5-methyl-lH-pyrazol-3-vpipyrimidin-4-amine; To a solution of 5-methyl-lH-pyrazol-3-amine (612 mg, 6.0 mmol) in absolute EtOH (10 ml) was added triethylamine (1.1 ml) and 2,4-dichloro-5-fluoropyrimidine (1.0 g, 6.0 mmol) and the resulting solution was aged at room temperature for 12 hours. The mixture was partitioned between EtOAc and water. The organic layer was washed with brine and dried.The solvents were removed under reduced pressure to give the title compound as a solid (679 mg). m/z: 228.

The synthetic route of 31230-17-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/49041; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 288148-34-5, A common heterocyclic compound, 288148-34-5, name is 1-Methyl-1H-pyrazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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.

In the 0 C, the 6-amino-2-(difluoromethyl)-7-methylquinolin-4-yl acetate (0.21 g, 0.8 mmol) and pyridine (10 ml) are added to the 50 ml single-port in the bottle, and then the 1-methylpyrazole-4-sulfonyl chloride (0.22 g, 1.2 mmol) is slowly added to the reaction system, after adding to rise to room temperature to continue the reaction 12 hours. After the reaction by adding ethyl acetate (30 ml), washed with water (20 ml x3), the organic phase is dried with anhydrous sodium sulfate, filtered, concentrated under reduced pressure of the filtrate, the residue by silica gel column chromatography separation [petroleum ether/ethyl acetate (v/v)=3/1], to obtain 162 mg yellow solid, yield: 49.4%.

The synthetic route of 288148-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dongguan Dongyang Guang Ke Research And Development Co., Ltd.; Li Yitao; Li Falin; Chen Tao; Xu Junxing; Yao Wenqiang; Lin Jian; Liu Xinshuo; (56 pag.)CN109320452; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 15754-60-6, The chemical industry reduces the impact on the environment during synthesis 15754-60-6, name is 1-(tert-Butyl)-1H-pyrazole, I believe this compound will play a more active role in future production and life.

To a mixture of 21.9 g of 1-tert-butyl-pyrazole in 150 mL DOM was added 31.5 g Nbromosuccinimide in portions between 0 and 10 00 The resulting mixture was stirred for 30 mm. The reaction mixture was allowed to reach ambient temperature. The precipitate was filtered off and washed with DOM. The combined organic extracts were washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield 34.0 g of 4-bromo-1-tert-butyl-pyrazole as oil.Analysis: HPLC-MS: R1 = 1 .35 mm (method B), M+H = 203 I 205

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; DAHMANN, Georg; GNAMM, Christian; FANDRICK, Daniel; SCOTT, John; MCCARTHY, Clive; (149 pag.)WO2017/42100; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35100-92-6, name is 1,5-Dimethyl-1H-pyrazol-3-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 35100-92-6, category: pyrazoles-derivatives

To an orange, homogeneous solution of methyl 2-oxo-2H-pyran-3-carboxylate (1.9201 g, 12.46 mmol) in DMF (12.44 ml) under nitrogen at 0 C was added 1,5- dimethyl-1H-pyrazol-3-amine (1.3 822 g, 12.44 mmol).. After 6 h, the cold bath wasremoved, and the reaction was stirred to room temperature for 15 mm EDCI (1-(3-dimethylaminopropyl) ethyl carbodiimide) (3.10 g, 16.17 mmol) and DMAP (0.380 g,3.11 mmol) were added. After stirring overnight, the reaction was diluted with EtOAc(200 mL) and water (50 mL). The layers were separated, and the organic layer waswashed with water (50 mL) and brine (50 mL), dried over Na2SO4, filtered andconcentrated in vacuo to give a residue which was purified by flash chromatographyusing an ISCO 330g column (solid loading) eluting with 10-100% EtOAc/hex. Appropriate fractions were collected and concentrated in vacuo to give methyl 1-(1,5- dimethyl- 1 H-pyrazol-3 -yl)-2-oxo- 1 ,2-dihydropyridine-3 -carboxylate (0.8397 g, 3.40 mmol, 27.3 % yield) as a light orange solid.

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; BRISTOL-MYERS SQUIBB COMPANY; LIU, Chunjian; LIN, James; MOSLIN, Ryan M.; WEINSTEIN, David S.; TOKARSKI, John S.; WO2015/89143; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 83-10-3, name is 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, 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 83-10-3, Computed Properties of C12H12N2O3

Step 2) N-(2-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide To a suspension of 4-amino-3-fluorophenol (1.0 g, 7.87 mmol) and 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (2.19 g, 9.44 mmol) in CH2Cl2 (20 mL) were added EDCI (3.02 g, 15.7 mmol) and HOAT (0.21 g, 1.57 mmol). The reaction mixture was refluxed for 20 hours, and then cooled to rt. Water (10 mL) was added and the mixture stirred at rt overnight, then filtered and the filter cake was washed with water (5 mL), followed by purifying by a silica gel column chromatography (CH2Cl2/MeOH (v/v)=70/1) to give the title compound as a beige white solid (1.25 g, 46.6%). MS (ESI, pos, ion) m/z: 342.1 [M+H]+, Rt=2.712 min.

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; Sunshine Lake Pharma Co., Ltd.; Calitor Sciences, LLC; Xi, Ning; Wu, Yanjun; Liao, Min; Feng, Yanming; US2015/37280; (2015); 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., Recommanded Product: Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate

Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate 2 (5.1 g, 25 mmol) and KOH (1.68 g, 30 mmol) were added to water (50 mL). The mixture was stirred for overnight, then acidified to pH = 1 using HCl, to give 3 as a white solid that was filtered off and dried with yield 83%, m.p. 200-201 C (Ref. m.p. 204-205 C) [38] , 1H NMR (400 MHz, CDCl3), delta 3.91 (s, 3H, N-CH3), 7.19 (t, J = 54.2 Hz, 1H, -CHF2), 8.31 (s, 1H, pyrazolyl-H), 12.73 (s, 1H, -COOH).

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 141573-95-7.

Reference:
Article; Liu, Xing-Hai; Zhao, Wen; Shen, Zhong-Hua; Xing, Jia-Hua; Xu, Tian-Ming; Peng, Wei-Li; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 881 – 889;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1029413-53-3, 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. 1029413-53-3, name is tert-Butyl 3-(4-amino-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Exam pie 20: Synthesis of I -(2-(2-(5-chioro-2-( I -(pyrroi id i n-3-yi)-I H-pyrazoi-4-yiamino) pyrimidin-4-yi)ethyi)phenyi)cyciopropanecarboxamide (20)(a) tert-Butyl 3-(4-(4-(2-(1-carbamoylcyclopropyl)phenethyl) -5-chloropyrimidin-2- ylamino)- 1H-pyrazol- 1-yI)pyrrolidine- 1-carboxylate (A21)A stirred solution of 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A 14 (0.150 g, 0.446 mmol), 4-amino-1-(1-Boc-pyrrolidin-3-yl)-1H-pyrazole (0.225 g, 0.892 mmol) in MeOH (10 mL) and water(1.0 mL) was heated at 70 C for 2 days. Additional 4-amino-1-(1-boc-pyrrolidin-3-yl)-1H-pyrazole (0.125 g, 0.446 mmol) was added and the mixture was heated for afurther 16 hours at reflux. After cooling the solvent was removed to afford a crude red oil which was purified by silica gel column chromatography (0-100% EtOAc in cyclohexane) to give the title compound A21 as a red oil (0.164 g, 67% yield). LCMSC: rt 5.51 mm; m/z 551.9 [M+H].

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 3-(4-amino-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; FOITZIK, Richard Charles; MORROW, Benjamin Joseph; HEMLEY, Catherine Fae; LUNNISS, Gillian Elizabeth; CAMERINO, Michelle Ang; GANAME, Danny; STUPPLE, Paul Anthony; LESSENE, Romina; KERSTEN, Wilhelmus Johannes Antonius; HARVEY, Andrew John; HOLMES, Ian Peter; WO2014/26243; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 37599-58-9, These common heterocyclic compound, 37599-58-9, name is (1H-Pyrazol-3-yl)methanamine, 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.

General procedure: To a solutionof the corresponding aldehyde (1.2 eq.; unless stated otherwise) in DMF (2 inL per 0.3 mmol of aldehyde; unless stated otherwise) was added the corresponding amine (2.5 eq.; unless stated otherwise) and the resulting solution was stirred at 25 C to form the corresponding inline. Then, the corresponding isocyano(tosyl)methyl)arene reagent (1 eq.; unless stated otherwise) and K2CO3 (1.5 eq.; unless stated otherwise*) were added and the reaction mixture was stirred at 25 C (unless stated otherwise). The reaction was stopped after the time indicated for each particular reaction. The reaction progress was monitored by TLC. (0083) A saturated aqueous solution of NH4CI (10 mL per 1 mmol of aldehyde) was added to the reaction mixture, which was then extracted with EtOAc (2 x 30 mL per 1 mmol of aldehyde). The combined organic extracts were washed with H2O (2 x 25 mL per 1 mmol of aldehyde), dried over MgSCC, filtered, and the solvent was evaporated in vacuo to provide the crude product. The residue obtained after the workup was purified using column chromatography or preparative TLC (unless stated otherwise). (0084) * note: in cases when the amine was used as HC1 salt, 4 eq. of K2CO3 were used

The synthetic route of 37599-58-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MASARYKOVA UNIVERZITA; BRYJA, Vitezslav; JANOVSKA, Pavlina; GREGOROVA, Michaela; NEMEC, Vaclav; KHIRSARIYA, Prashant; PARUCH, Kamil; (171 pag.)WO2019/185631; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics