Category: pyrazoles-derivatives

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. 72760-85-1, name is 3-Amino-5-(methylthio)-1H-pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 72760-85-1

General procedure: A mixture of pyrazole-imines 7 (1 mmol), aldehyde (1 mmol), TMSCN (1.2 mmol) in [Bmim]BF4 (0.5 g) was heated at 120 C for 24 h. After cooling, the reaction mixture was washed with water (5 mL) and the residue washed with MeOH to afford pure product 8.

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:
Article; Goli, Shokoufe; Mirzaei, Peiman; Bazgir, Ayoob; Journal of the Iranian Chemical Society; vol. 15; 12; (2018); p. 2803 – 2809;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 78208-72-7, name is Ethyl 3-isopropyl-1H-pyrazole-5-carboxylate, 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 78208-72-7, Formula: C9H14N2O2

Preparation 14 5-ISOPROPYL-1-R2- (TETRAHVDRO-PVRAN-2-YLOXV)-ETHYLL-1 H-PYRAZOLE-3-CARBOXYLID ethyl ester The ester of preparation 6 (509mg, 2. 8MMOL), 2- (2-bromoethoxy) tetrahydro-2H- pyran (732mg, 3. 5MMOL) and potassium carbonate (483mg, 3. 5MMOL) were dissolved in 1-methyl-2-pyrrolidinone (5mL) and the reaction mixture heated to 80°C for 18 hours. The reaction mixture was cooled, poured into ethyl acetate, washed with water (x 2) and brine, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with pentane: ethyl acetate 80: 20 to 60: 40 to yield the title product, 663mg (76percent). HNMR (CD3, 400MHZ) : 1.25 (d, 6H), 1.37 (t, 3H), 1.44-1. 71 (m, 6H), 2.97 (m, 1 H), 3.42 (m, 1 H), 3.54 (m, 1 H), 3.75 (m, 1 H), 4.00 (m, 1 H), 4.32 (m, 2H), 4.54 (t, 1 H), 4.68 (m, 1 H), 4.76 (m, 1 H), 6.64 (s, 1 H). MS ES+ M/Z 227 [MH] +

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; PFIZER LIMITED; PFIZER INC.; WO2005/9965; (2005); 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. 180207-57-2, name is 2-(1H-Pyrazol-4-yl)ethanol belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C5H8N2O

General procedure: To a mixture of 3,6-dichloropyridazine (3.73 g, 25 mmol), 4(5)-Hydroxymethylimidazole (1.96 g, 20 mmol), and Cs2CO3 (8.14 g, 25 mmol) was added acetonitrile (80 mL). The mixture was refluxed for 3 h and was poured into H2O (200 mL). 1N HCl(aq) was added slowly until the pH is ca. 7-8. Then the aqueous layer was extracted with EtOAc (150 mL) and then CH2Cl2 (100 mL x 5). The combined organic layer was dried (Na2SO4) and filtered. After removal of solvent, the product was triturated with 10% CH2Cl2/Et2O (30 mL x 3) to give 1.74 g of product. The filtrate was concentrated and was purified by column using 60-70-80% EtOAc/(CH2Cl2/hexane=1/1) as the eluent to give 629 mg of prouct. Total 2.36g of D (53%) was obtained.

The synthetic route of 180207-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Shyh-Ming; Tang, Yuting; Rano, Thomas; Lu, Huajun; Kuo, Gee-Hong; Gaul, Michael D.; Li, Yaxin; Ho, George; Lang, Wensheng; Conway, James G.; Liang, Yin; Lenhard, James M.; Demarest, Keith T.; Murray, William V.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 5; (2014); p. 1437 – 1441;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 82668-50-6, 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. 82668-50-6, name is Ethyl 2-(3-Pyrazolyl)acetate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 2-(1H-pyrazol-3-yl)acetate (180 mg, 1.17 mmol), caesium carbonate (762 mg, 2.34 mmol) and N,N-dimethylformamide (2 mL) were added in a 25 mL single-neck flask. After cooling in an ice bath, methyl iodide (332 mg, 2.34 mmol) was added dropwise, and the reaction was continued for 2 hours in an ice bath. After completion of the reaction monitored by TLC, water (20 mL) was added. Then mixture was extracted with ethyl acetate (3?10 mL), and the organic layers were combined and dried over anhydrous sodium sulfate. Solvent was removed in vacuo to afford a mixture of ethyl 2-(1-methyl-1H-pyrazol-3-yl)acetate and ethyl 2-(1-methyl-1H-pyrazol-5-yl)acetate (yellow oil, 136 mg). Step 5: 2-(1-Methyl-1H-pyrazol-5-yl)acetic acid and 2-(1-methyl-1H-pyrazol-3-yl)acetic acid (0079) The mixture of ethyl 2-(1-methyl-1H-pyrazol-3-yl)acetate and ethyl 2-(1-methyl-1H-pyrazol-5-yl)acetate (136 mg, 0.81 mmol), lithium hydroxide monohydrate (102 mg, 2.43 mmol) and ethanol/H2O (2 mL/0.5 mL) were added in a 25 mL single-neck flask, and the mixture was reacted at room temperature for 0.5 hour. After completion of the reaction, ethanol was removed under reduced pressure, then water (2 mL) was added. The mixture was adjusted to pH 3 with 1N hydrochloric acid and extracted with ethyl acetate (3 10 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo to remove the solvent to give a product (yellow oil, 100 mg). Step 6: Synthesis of N-(2,6-dichloro-3′-cyano-4′-isobutyl-[1,1′-biphenyl]-4-yl)-2-(1-methyl-1H-pyrazol-3-yl)acetami de (9A) and N-(2,6-dichloro-3′-cyano-4′-isobutyl-[1,1′-biphenyl]-4-yl)-2-(1-methyl-1H-pyrazol-5-yl)acetami de (9B) (0080) 4′-Amino-2′,6′-dichloro-4-isobutyl-[1,1′-biphenyl]-3-carbonitrile (40 mg, 0.13 mmol), the mixture of 2-(1-methyl-1H-pyrazol-5-yl)acetic acid and 2-(1-methyl-1H-pyrazol-3-yl)acetic acid (44 mg, 0.32 mmol), HATU (118 mg, 0.38 mmol), N,N-diisopropylethylamine (50 mg, 0.39 mmol) and dichloromethane (2 mL) were added in a 25 mL single-neck flask, and the mixture was reacted at room temperature for 4 hours. The resulting crude product was separated by preparative thin layer chromatography (petroleum ether: ethyl acetate = 1:1) to give N-(2,6-dichloro-3′-cyano-4′-isobutyl-[1,1′-biphenyl]-4-yl)-2-(1-methyl-1H-pyrazol-3-yl)acetami de (white aolid, 26 mg), 1H NMR (400 MHz, CDCl3) delta 9.23 (s, 1H), 7.66 (s, 2H), 7.47 (s, 1H), 7.33 (t, J = 7.4 Hz, 4H), 6.19 (s, 1H), 3.93 (s, 3H), 3.75 (s, 2H), 2.75 (d, J = 7.3 Hz, 2H), 2.02 – 1.97 (m, 1H), 0.97 (d, J = 6.6 Hz, 6H). MS (ESI) m/z: 441.0 (M+1) and N-(2,6-dichloro-3′-cyano-4′-isobutyl-[1,1′-biphenyl]-4-yl)-2-(1-methyl-1H-pyrazol-5-yl)acetami de (white aolid, 27 mg), 1H NMR (400 MHz, CDCl3) delta 8.26 (s, 1H), 7.63 (s, 2H), 7.47 (d, J = 3.3 Hz, 2H), 7.34 (s, 2H), 6.26 (s, 1H), 3.87 (s, 3H), 3.80 (s, 2H), 2.75 (d, J = 7.3 Hz, 2H), 1.97 – 1.88 (m, 1H), 0.97 (d, J = 6.6 Hz, 6H). MS (ESI) m/z: 440.9 (M+1).

The synthetic route of Ethyl 2-(3-Pyrazolyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fudan University; WANG, Yonghui; HUANG, Yafei; QIU, Ruomeng; TANG, Ting; (68 pag.)EP3581561; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 368870-03-5, 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. 368870-03-5, name is (4-(1H-Pyrazol-1-yl)phenyl)methanamine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4-(Pyrazol-1-yl)benzylamine (12.2 g, 0.07 mol) was dissolved in 50 mL of 2-methoxyethanol (75 mL) and 3-isopropyl-pyrimidine-5,7-dithiol (2) (13.3 g, 0.059 mol) was added under an atmosphere of nitrogen. The reaction mixture was heated at 120 C for 12 hours. The reaction product crystallized upon cooling to 10-15 C and was filtered off. After washing with 2-methoxyethanol, then THF, and drying in vacuo at 75 C, 13.7 g of product are obtained in 62% yield. The analytical sample was recrystallized from DMS0/H20, dried at 75 C under vacuum; m.p. 268-270 C (decomposition), UV (nm): 268 l, 288 l, 300 l, 336 l?. MS ESI+ 366.1 (M+H)+, ESI- 364.1 (M-H) . NMR (500 MHz; DMSO-d6): 1.23 (d, / = 7.03 Hz, 6H, -CH(C//3)2); 3.44 (bs, 1H, -C//(CH3)2); 4.75 (d, J = 6.11 Hz, 2H, -NH-G-); 6.50-6.51 (m, 1H, HAT); 7.46 (d, / = 7.95 Hz, 2H, HAT); 7.71 (d, / = 1.53 Hz, 1H, HAT); 7.79 (d, J = 8.25 Hz, 2H, HAT) ; 8.45 (d, J = 2.45 Hz, 1H, HAT) ; 9.17 (bs, 1H, -NH-); l2.23(bs, 1H, -NH); 13.74 (bs, 1H, -SH). 13C (125 MHz; DMSO-d6): 21.8; 42.4; 107.7; 118.3; 127.6; 128.7; 138.7; 140.8. Anal. (CI8H19N7S) C, H, N, S.

The synthetic route of (4-(1H-Pyrazol-1-yl)phenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERZITA PALACKEHO V OLOMOUCI; USTAV EXPERIMENTALNI BOTANIKY AV CR, V.V.I.; HAVLICEK, Libor; STURC, Antonin; REZNICKOVA, Eva; JORDA, Radek; KRYSTOF, Vladimir; STRNAD, Miroslav; (66 pag.)WO2019/149295; (2019); A1;,
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. COA of Formula: C3H3IN2

INTERMEDIATE 18 3 -Fluoro-4-(3 -iodo- 1 H-pyrazol- 1 – vDpyridine To a solution of 3-iodopyrazole (0.70 g, 3.61 mmol) in DMSO (15.1 mL) was added sodium hydride (60% in oil, 0.159 g, 3.97 mmol) and stirred for 0.5 h before 3,4- difluoro pyridine (0.415 g, 3.61 mmol) was added. The reaction mixture was stirred at 90 C for 2.5 h. The reaction 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- fluoro-4-(3-iodo-lH-pyrazol-l-yl)pyridine, as a white solid. LCMS calc. = 289.95; found = 289.92 (M+H)+. NMR (500 MHz, CDC13): delta 8.61 (d, J= 3.8 Hz, 1 H); 8.48 (d, J= 5.4 Hz, 1 H); 8.02 (d, J= 2.4 Hz, 1 H); 8.00 (d, J= 5.4 Hz, 1 H); 6.70 (d, J= 2.5 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

Reference of 181585-93-3, The chemical industry reduces the impact on the environment during synthesis 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate, I believe this compound will play a more active role in future production and life.

5-Nitro-3-pyrazole-carboxylic acid methyl ester (22.35 g, 130.61 mmol) is dissolved in each 160 mL THF und glacial acetic acid. Then, Pd-C (10%, 4.36 g) are added and the reaction is stirred for 6 days under hydrogen atmosphere at RT. Then, the mixture is filtered over celite and the solvent is removed under vacuum. The crude material is dissolved in methylene chloride (800 mL) and sodium hydrogen carbonate (200 g) are added, filtered and the solvent is again removed under vacuum. This procedure is repeated until the acetic acid smell is lost. 5-Amino-3-pyrazole-carboxylic acid methyl ester is isolated in high yields (16.91 g, 91.7%).

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

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; US2008/32998; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 39806-90-1, name is 4-Iodo-1-methyl-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. SDS of cas: 39806-90-1

General procedure: 4-Iodo-1-methyl-1H-pyrazole 1 (101 mg, 0.5 mmol) and phenylboronic 2 (59 mg, 0.5 mmol) were dissolved in DME (3 mL) and H2O (1.2 mL) in a microwave vial under a nitrogen atmosphere. Pd(PPh3)4 (2 mmol%, 11.6 mg) and Cs2CO3 (407.3 mg, 1.25 mmol) were added, and the reaction mixture was irradiated in a microwave apparatus at 90 C for 5-12 min. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by silica gel column chromatography using petroleum ether/acetone as eluent to give the title compound.

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

Reference:
Article; Cheng, Hua; Wu, Qiong-You; Han, Fan; Yang, Guang-Fu; Chinese Chemical Letters; vol. 25; 5; (2014); p. 705 – 709;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 14521-81-4, The chemical industry reduces the impact on the environment during synthesis 14521-81-4, name is 3-Fluoro-1H-pyrazole, I believe this compound will play a more active role in future production and life.

A mixture of (5)-S -chloro-N-( 1 -cyclopropyl-2,2,2-trifluoroethyl)-7-methylpyrazolo[ 1,5 -aj pyrimidine-3 -carboxamide (70 mg, 0.21 mmol), 3-fluoro- 1H-pyrazole(18 mg, 0.21 mmol), and K2C03 (58 mg, 0.42 mmol) in DMF (2 mL) was stirred at 60 C for 2 h, poured into H20 (10 mL), and extracted with EA (30 mL x 3). The combined organic phases were washed with H20 (50 mL) and brine (50 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel columnchromatography (PE/EA = 2/1) and preparative HPLC (10 mM NH4HCO3/MeCN) to afford thetitle compound (14 mg, 24%) as a white solid. ?H NMR (400 MHz, MeOD-d4): 5 8.59 (s, 1H),8.55 (t, J= 2.4 Hz, 1H), 7.65 (s, 1H), 7.44 (q, J= 2.8 Hz, 1H), 4.36-4.30 (m, 1H), 2.92 (s, 3H),1.40-1.34 (m, 1H), 0. 82-0.75 (m, 1H), 0.70-0.58 (m, 2H), 0.52-0.46 (m, 1H). LC-MS m/z:383.1 [M+Hj. HPLC: Purity (214 nm): 93%; tR= 8.83 min.

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-Fluoro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; BOURQUE, Elyse Marie Josee; LANSBURY, Peter, T.; GOOD, Andrew, C.; (391 pag.)WO2017/176960; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 4058-91-7, These common heterocyclic compound, 4058-91-7, name is 5-Amino-1-methyl-1H-pyrazole-4-carboxylic acid, 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.

0.47g first After completion of the reaction, first substitution reaction 3h; after completion 0 C of the dropwise addition, 10 ml cooling, circulating water, and vacuum distillation, to obtain a yellow viscous solid, namely second intermediate (1 – methyl -5 – amino – 111H-pyraz -4 -benzoyl chloride); after completion of the dropwise addition reaction, is carried out under stirring.

Statistics shows that 5-Amino-1-methyl-1H-pyrazole-4-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 4058-91-7.

Reference:
Patent; Nankai University; Li Huabin; Li Luyang; Gu Jian; Kuang Xinyi; Xia Zhe; Zhang Shangzhong; Guo Lihui; Chen Rui; (16 pag.)CN110066282; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics