Month: July 2021

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. 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole, A new synthetic method of this compound is introduced below., Formula: C5H9N3

General procedure: 3-methyl-1-phenyl-1H-pyrazol-5-amine (1 mmol, 173 mg) and acetophenone (1.5 mmol, 180 mg), CuI (10 mol %, 19 mg) and FeCl3.6H2O (10 mol %, 27 mg) were added in DMSO (2 mL) at 120C in a round-bottom flask equipped with a magnetic stirring bar and a reflux condenser. After completion of the reaction the organic mixture was extracted with ethyl acetate (3×50 mL) and then washed with brine solution. The organic fraction was dried with anhydrous sodium sulphate and concentrated in rotavapor under vacuum. The product was purified by column chromatography using silica gel (100-200 mesh, ethyl acetate/hexane as eluent).

The synthetic route of 3524-32-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rastogi, Gaurav K.; Saikia, B-Shriya; Pahari, Pallab; Deb, Mohit L.; Baruah, Pranjal K.; Tetrahedron Letters; vol. 60; 17; (2019); p. 1189 – 1192;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 4522-35-4, name is 3-Iodo-1H-pyrazole, molecular formula is C3H3IN2, 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. Recommanded Product: 4522-35-4

INTERMEDIATE 16 3-(3-Iodo-lH-pyrazol-l-yl)-5-(trifluorometyl pyridine To a solution of 3-iodopyrazole (0.70 g, 3.61 mmol), in DMSO (15.0 mL) was added sodium hydride (60% in oil, 0.159 g, 3.97 mmol), and stirred for 0.5 h before 3- fluoro-5-trifluoromethylpyridine (0.596 g, 3.61 mmol) was added. The reaction mixture was stirred at 90 C overnight. This was quenched by the addition of water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combiflash, 40 g, 0-20 % EtOAc in hexanes) to give 3-(3-iodo-lH-pyrazol-l-yl)-5-(trifluorometyl)pyridine, as a white solid. LCMS calc. = 339.95; found = 339.86 (M+H)+. 1H NMR (500 MHz, CDC13): delta 9.12 (br s, 1 H); 8.83 (br s, 1 H); 8.32 (br s, 1 H); 7.85 (br s, 1 H); 6.73 (d, J= 1.7 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4522-35-4, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 1393128-21-6, name is 4-(Methylthio)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C4H6N2S

To a solution of SB-FF (100 mg, 0.24 mmol) in DMF (2 mL) was added Al (55 mg, 0.48 mmol) and K2CO3 (100 mg, 0.72 mmol) at 19C. The reaction was stirred at 19C for 16 h. The resulting mixture was poured into water (3 ml). The mixture was extracted with EtOAc (2 mL x 3). The combined organic layers was washed with brine (5 mL), dried over Na2S04 and concentrated in vacuum. The residue was purified by silica gel column (Petroleum ether/ethyl acetate = 10/1 to 3/1) to give SB-14 (80 mg, yield: 74%) as a pink solid. 1H NMR: (400 MHz, CDC13) delta 7.53 (s, 1H), 7.43 (s, 1H), 4.79-4.97 (m, 2H), 4.47-4.65 (m, 1H), 2.56-2.63 (m, 1H), 2.35 (s, 3H), 2.19-2.26 (m, 1H), 2.00-2.08 (m, 2H), 1.63-1.92 (m, 5H), 1.35-1.57 (m, 5H), 1.20-1.1.32 (m, 5H), 1.07-1.18 (m, 5H), 0.75-0.91 (m, 1H), 0.71 (s, 3H). LCMS: rt = 1.25 mm, m/z = 449.2 [M+H]+

The synthetic route of 1393128-21-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGE THERAPEUTICS, INC.; BOTELLA, Gabriel Martinez; HARRISON, Boyd L.; ROBICHAUD, Albert Jean; SALITURO, Francesco G.; BERESIS, Richard Thomas; WO2014/169833; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 37687-24-4, The chemical industry reduces the impact on the environment during synthesis 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, I believe this compound will play a more active role in future production and life.

[00590] 7rt-Butyl-[(2R)-2-hydroxypropyl]carbamate (6.46 g, 36.86 mmol) was added to a stirred solution of diethyl-3,5-pyrazoledicarboxylate (3.9 g, 18.43 mmol), triphenylphosphine (8.7 g, 33.18 mmol) and DTBAD (7.64 g, 33.18 mmol) in THF (150 mL) at 0 C. The mixture was stirred at 80 C for 16 h. The solvent was then evaporated in vacuo, the crude product purified first by open column chromatography (silica; DCM 100%) and then by flash column chromatography (silica, DCM in Heptane 0/100 to 100/0 and then EtOAc in DCM 0/100 to 50/50). The desired fractions were collected and the solvents evaporated in vacuo to yield diethyl-l- {(l*5)-2-[(tert-butoxycarbonyl)amino]-l- methylethyl}-lH-pyrazole-3,5-dicarboxylate as a white (7.6 g, 20% purity, 22 % yield).

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, Diethyl 3,5-pyrazoledicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VANDERBILT UNIVERSITY; CONN, P., Jeffrey; LINDSLEY, Craig, W.; STAUFFER, Shaun, R.; BARTOLOME-NEBREDA, Jose Manuel; CONDE-CEIDE, Susana; MACDONALD, Gregor, James; TONG, Han Min; ALCAZAR-VACA, Manuel Jesus; ANDRES-GIL, Jose Ignacio; WO2013/192350; (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. 64781-79-9, name is 4-Methyl-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Methyl-1H-pyrazol-3-amine

EXAMPLE 28 3-Methyl-7-(3-thienyl)pyrazolo[1,5-a]pyrimidine A mixture of 0.01 mole of 3-dimethylamino-1-(3-thienyl)-2-propen-1-one and 0.01 mole of 3-amino-4-methylpyrazole in glacial acetic acid is heated at reflux temperature for 8 hours. The solvent is removed in vacuo to give the product of the example.

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; American Cyanamid Company; US4281000; (1981); A;,
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. 3469-69-0, name is 4-Iodopyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 3469-69-0

1-Trityl-4-iodopyrazole The title compound was prepared by combining 4-iodopyrazole (10 g, 52 mmol), triphenylmethyl chloride (14.4 g, 51.6 mmol), triethylamine (NEt3) (7.2 mL, 52 mmol), and DMF (80 mL). After stirring overnight, the mixture was poured onto ice water. The precipitated solid was collected and recrystallized to give the title compound as a solid, mp 193-194 C. 1H NMR (CDCl3): delta7.11 (m, 6 H), 7.32 (m, 9 H), 7.41 (s, 1 H), 7.67 (s, 1 H).

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; Warner-Lambert Company; US6528510; (2003); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 141573-95-7, name is Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-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. Quality Control of Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate

To the toluene layer was added 25% caustic soda solution159 g (0.994 mole) of the compound were added thereto, and the mixture was heated to 65 DEG C and stirred for 45 minutes. The aqueous layer was separated, and 54 g of water and 160.2 g (1.54 mole) of 35% hydrochloric acid were added to the toluene layer, followed by stirring at 85 for 15 minutes. After cooling to room temperature the resulting crystals were filtered, washed with 180 g of water and dried in vacuo at 60 & lt; RTI ID = 0.0 & gt;To obtain 155.8 g (yield 98%) of 3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxylic acid.

The synthetic route of Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Buheung Industries Co., Ltd.; Ahn, Kyung Wook; Kim, Jong Nam; Wang, Kyu Jung; Noh, Dong Won; Seo, Nan Young; Kim, Sin Ae; Wei, Sung Han; (10 pag.)KR2016/120009; (2016); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 2075-46-9,Some common heterocyclic compound, 2075-46-9, name is 4-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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.

The solution of 4-nitro-1H-pyrazole (SM6, 10 g, 88.44 mmol), NaH(60%, 1.3 eq, 4.60 g, 114.97mmol) and iodomethane (SM7, 25 g, 177 mmol) in Dry DMF (100 ml) was stirred at 0C overnight, and then cooled to room temperature and quenched with water (200 mL) and extracted with EA. The organic layer was dried over anhydrous Na2SO4 to obtain the target compound 12(11 g, 92 % yield).

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

Reference:
Patent; Hangzhou Rex Pharmaceutical Co., Ltd; WANG, Yonghui; ZHOU, Juan; GAO, Yujun; WANG, Dong; HONG, Binbin; SHEN, Ximing; WU, Yaodong; LI, Chunqi; EP3476848; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1146629-77-7, name is (4-(1H-Pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate, 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 1146629-77-7, Formula: C15H17N5O2

37 in acetonitrile (619mg, 2.07mmol, Lin, Q. et al. Org. Lett., 2009, 11, to a solution (15mL) of the is preparation) described in 1999-2002, 51 (673mg, 5.17mmol), followed by the addition of DBU (650muL, 4.35mmol). The reaction was stirred for 15 hours at room temperature, and concentrated under reduced pressure. The resulting mixture of crude was diluted with water, and extracted with ethyl acetate (3x50mL). The combined organic layers were washed with 1N HCl, dried (Na2SO4), filtered and concentrated under reduced pressure. Normal phase column chromatography (SiO2, 0~60% ethyl acetate / hexanes) Purification on to give a white foam (+/-)-52 (447mg, 50%).

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; Concert Pharmaceuticals Inc.; Ai, Robert Silverman; Julie, F. Liu; Adam, J. Morgan; Bhomick, Panda; Scott, EL. Habeson; (43 pag.)JP2015/117185; (2015); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 2075-46-9, A common heterocyclic compound, 2075-46-9, name is 4-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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.

To a solution of 4-nitro-1H-pyrazole (2.5 g, 22.11 mmol) in THF (50 mL) wasadded NaH (0.973 g, 24.32 mmol) and the mixture was stirred at rt for 5 mm. To thissuspension was then added CH3I (1.382 mL, 22.11 mmol) and stirred at rt overnight. The reaction mixture was then diluted with EtOAc (2 x 25 mL) and washed with brine (25 mL). The organic layer was concentrated, followed by purification using normal phase chromatography to yield 1-methyl-4-nitro-1H-pyrazole as white solid (1.9 g, 80% yield).?H NMR (400 MHz, CDC13) oe ppm 8.12 (s, 1H), 8.06 (s, 1H), 3.97 (s, 3H).

The synthetic route of 2075-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics