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. 16617-46-2, name is 3-Amino-1H-pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., name: 3-Amino-1H-pyrazole-4-carbonitrile

To a solution of 3-amino-4-cyanopyrazole (100 g, 0.9 mol) in DMF (1 L) is added NBS (197.5 g, 1.1 mol) and mixture is stirred for 10 h at ambient temperature. The mixture is concentrated in vacuo then dissolved in EtOAc and washed with brine (8×). The organics are collected and concentrated in vacuo to afford I-70 (50 g, 29%) m/z 187.0 [M+].

The synthetic route of 16617-46-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BENTZIEN, Joerg Martin; BERRY, Angela Kay; BOSANAC, Todd; BURKE, Michael Jason; DISALVO, Darren Todd; HORAN, Joshua Courtney; LIANG, Shuang; MAO, Can; MAO, Wang; SHEN, Yue; SOLEYMANZADEH, Fariba; ZINDELL, Renee M.; US2014/45813; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 127107-23-7, 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. 127107-23-7, name is 1-Methyl-1H-pyrazol-4-amine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

Step 4) fert-butyl 5-((5-chloro-2-((l-methyl-lH-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-5- (cvanomethyl)hexahydrocvclopentarc1pyrrole-2(lH)-carboxylate [0464] To a suspension of tert-butyl 5-(cyanomethyl)-5-((2,5-dichloropyrimidin-4-yl)amino) hexahydrocyclopenta[c]pyrrole-2(lH)-carboxylate (631.5 mg, 1.53 mmol) and 1-methyl-lH- pyrazol-4-amine hydrochloride (213.2 mg, 1.60 mmol) in -BuOH (10 mL) was added Et3N (322.1 mg, 3.18 mmol). The reaction mixture was stirred at 150 C in a sealed tube overnight and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v) = 1/50) to give the title compound as a yellow solid (283.0 mg, yield 39.1%). LC-MS (ESI, pos. ion) m/z: 473.3 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-pyrazol-4-amine hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; LI, Xiaobo; CHEN, Wuhong; ZHANG, Tao; HU, Haiyang; DAI, Weilong; WU, Yanjun; (192 pag.)WO2017/44434; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 17635-45-9, name is 4-Pyrazol-1-yl-phenylamine, 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 17635-45-9, Quality Control of 4-Pyrazol-1-yl-phenylamine

General procedure: A dry 50 mL capacity carousel reaction tube was charged with the relevant substituted indole (1.5 mmol), and this starting material dissolved in dry THF (12 mL). Oxalyl chloride (144 muL, 209 mg, 1.65 mmol) was added and the mixture stirred at room temp. After 24 h, either N,N-diisopropylethylamine (590 muL, 438 mg, 3.4 mmol) or 2,6-lutidine(396 muL, 364 mg, 3.4 mmol) was introduced to the reaction, followed by the relevant amine (1.8 mmol). The temperature was raised to 45 °C, and heating continued for 18 h. The solvent was evaporated, then the residue resuspended in a mixture of ethyl acetate (20 mL) and brine (10 mL) and stirred vigorously for 30 min. After passing through a liquid-liquid extraction column, ensuring washing through of the column with additional ethyl acetate, a second extraction was carried out with sat. NH4Cl (10 mL) in the same manner. Product solutions were then evaporated to dryness giving the crude indole-3-glyoxylamide derivatives, which were purified as necessary (see Supplementary Information for individual compound details). Typically, two sequential recrystallizations, from ethyl acetate-hexane followed by 2-propanol-water, afforded final products of good purity. For products derived from poorly nucleophilic anilines (p-1H-pyrazol-1-ylaniline,p-pyrrol-1-ylaniline and p-morpholinoaniline), a further modification was used. Immediately following introduction of the arylamine to the reaction mixture, DMAP (18 mg, 0.15 mmol, 10 molpercent) was added to assist the final step, as its use was found to enhance the extent of conversion in the final step in such cases.

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, 4-Pyrazol-1-yl-phenylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Thompson, Mark J.; Louth, Jennifer C.; Ferrara, Steven; Jackson, Matthew P.; Sorrell, Fiona J.; Cochrane, Edward J.; Gever, Joel; Baxendale, Sarah; Silber, B. Michael; Roehl, Henry H.; Chen, Beining; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4125 – 4132;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 72760-85-1, name is 3-Amino-5-(methylthio)-1H-pyrazole-4-carbonitrile, 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 72760-85-1, Product Details of 72760-85-1

General procedure: An equimolar mixture of Int-I (chalcones) and Int-II (5-amino-3-(methylthio)-1H-pyrazole-4-carbonitrile) was refluxed in n-butanol for 4-5 h. The completion of reaction was confirmed by Thin Layer Chromatography using (6:4- hexane: ethyl acetate) as a mobile phase. The reaction mixture was then allowed to cool and the resulting solid was filtered and washed with diethyl ether to remove impurities. The procedure was repeated 3-4 times to free the product from impurities.

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; Baluja, Shipra; Nandha, Kajal; Journal of Molecular Liquids; vol. 201; (2015); p. 90 – 95;,
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. 948570-75-0, name is 1-(2-Methoxyethyl)-4-nitro-1H-pyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

1-(2-methoxyethyl)-4-nitro-1H-pyrazole (84 mg, 0.49 mmol) and -chloro-6-(2,6-dichloro-3,5-dimethoxy phenyl)pyrido[3,4-d]pyrimidine (200 mg, 0.54 mmol) were dissolved into DMA (15 mL), then CuI (112 mg, 0.59 mmol), PivOH (15 mg, 0.15 mmol), K2CO3 (88 mg, 0.64 mmol) and Pd(PPh3)2Cl2 (34 mg, 0.05 mmol) were added, the mixture was heated to 140 C. under N2 and stirred for 1 h. The reaction was completed, and the mixture was concentrated to remove the sol vent by reduced pressure and separated by fast silica gel column (PE/EA 2:1) to obtain compound 6-(2,6-dichloro-3,5-dimethoxyphenyl)-2-(1-(2-methoxyethyl)-4-nitro-1H-pyrazol-5-yl)pyrido[3,4-d]pyrimidine (103 mg, yield 42%). MS m/z (ESI): 505 [M+1]+.

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; Abbisko Therapeutics Co., Ltd.; YANG, Fei; DENG, Haibing; YING, Haiyan; YU, Hongping; CHEN, Zhui; XU, Yaochang; (604 pag.)US2019/270742; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-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. Product Details of 578008-32-9

Intermediate 90(S)-4-(3-((tert-Butyldimethylsilyloxy)methyl)morpholino)-6-(l-(3,5-difluoropyridin-2-vD-2- methoxyethoxy)-5-fluoro-N-(5-methyl-lH-pyrazol-3-yl)pyrimidin-2-amine (3,S<)-3-({[fert-Butyl(dimethyl)silyl]oxy}methyl)-4-{2-chloro-6-[l-(3,5-difluoropyridin-2-yl)-2- methoxyethoxy]-5-fluoropyrimidin-4-yl}morpholine (Intermediate 62), tert-butyl 3-amino-5- methyl-lH-pyrazole-1-carboxylate (Intermediate 10), BINAP, Pd2(dba)3, and CS2CO3 in dioxane (2 ml) was heated at 950C for 8h. LCMS indicated complete reaction. Methanol (1 ml) was added and the reaction was stirred at r.t for Ih. Solvent was removed under reduced pressure and the reaction mixture was purified by ISCO column. The material obtained was directly used in the subsequent step without further purification. LCMS: 610[M+eta]+. The synthetic route of tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate has been constantly updated, and we look forward to future research findings. Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/132502; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1260243-04-6,Some common heterocyclic compound, 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, molecular formula is C6H9N3O2, 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 mixture of ethyl 5-amino-1H-pyrazole-4-carboxylate obtained in the step 1) (15.5 g, 0.01 mol) and 1-p-fluorophenyl-4,4,4 , -trifluorobutanedione (23.4 g, 0.1 mol) was placed in a vessel; 3.2) Dissolve the mixture in a container with 50 ml of glacial acetic acid to give a mixture E, placing the container on an electric heating barHeating to 115 ° C;3.3) The mixture E was heated to reflux for 7 hours, cooled, allowed to stand, and precipitated as a yellow-green needle-like solid;Ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [l, 5-a] pyrimidine-3-carboxylate was obtained after filtration, washing and drying;The process used in the process is cold glacial acetic acid.The mass of the product ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [l, 5_a] pyrimidine-3-carboxylate obtained in 27.05 g. Yield: 76.63percent.

The synthetic route of 1260243-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chongqing Medical College; Shi, Lei; Niu, Ya Hui; (7 pag.)(2016);,
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. 17635-45-9, name is 4-Pyrazol-1-yl-phenylamine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Pyrazol-1-yl-phenylamine

General procedure: A mixture of aniline derivative 1a?1e (1 mmol) and 1 cm3concentrated hydrochloric acid was thoroughly stirred atroom temperature for 15 min and then cooled to 0 C. Asolution containing 0.069 g sodium nitrite (1 mmol) in 10 cm3 water was added dropwise to the initial mixtureduring 40 min. An aqueous solution of aromatic nucleophile(1 mmol) in NaOH 10percent (5 cm3) was then addedand the resulted mixture was stirred for 1 h at 0 C. Theprecipitated solid was filtered, washed with water and dried in air. The products 2a?2c, 2e, 2f, 2m, and 2o were purifiedby recrystallization in ethanol, but preparative TLC (nhexane?EtOAc, 4:1) was applied for purification of products2d, 2g?2l, 2n, and 2p.

According to the analysis of related databases, 17635-45-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ghasemi, Zarrin; Azizi, Sajjad; Salehi, Roya; Kafil, Hossein Samadi; Monatshefte fur Chemie; vol. 149; 1; (2018); p. 149 – 157;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 15878-00-9, name is 4-Chloro-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. Application In Synthesis of 4-Chloro-1H-pyrazole

2-Amino-4-(4-chloro-pyrazol-1-yl)-6-methylsulfanyl-pyrimidine-5-carbonitrile From 2-amino-4-bromo-6-methylsulfanyl-pyrimidine-5-carbonitrile, 4-chloropyrazole and cesium carbonate in NMP. EI-MS m/e (%): 269 (M{37Cl}+H+, 30). 267 (M{35Cl}+H+, 100).

The synthetic route of 4-Chloro-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Borroni, Edilio Maurizio; Huber-Trottmann, Gerda; Kilpatrick, Gavin John; Norcross, Roger David; US2001/27196; (2001); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 14531-55-6, The chemical industry reduces the impact on the environment during synthesis 14531-55-6, name is 3,5-Dimethyl-4-nitro-1H-pyrazole, I believe this compound will play a more active role in future production and life.

(a)1-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-3,5-dimethyl-4-nitro-pyrazoleTo a cold (0 C) solution of 3,5-dimethyl4nitro-1 H-pyrazole (250 mg, 1.77 mmol),triethylene glycol monomethylether (482 IJL, 3.01 mmol) and triphenylphosphine (789 mg, 3.01mmol) in THF (10 mL) was added dropwise a solution of 40% DEAD in toluene (1.31 mL, 3.01 mmol) The reaction mixture was allowed to warm to room temperature and was stirred for 3 h. Ethyl acetate was added and washed with a 10% NaCI-solution. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography(DCM/MeOH = 99/1 to 95/5 v/v%) to afford 1-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-3,5- dimethyl-4-nitro-pyrazole (1 .7 g, crude) which was used directly in the next step.

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, 3,5-Dimethyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NETHERLANDS TRANSLATIONAL RESEARCH CENTER B.V.; DE MAN, Adrianus Petrus Antonius; BUIJSMAN, Rogier Christian; STERRENBURG, Jan Gerard; UITDEHAAG, Joost Cornelis Marinus; DE WIT, Joeri Johannes Petrus; ZAMAN, Guido Jenny Rudolf; WO2015/155042; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics