Day: September 2, 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. 51985-95-6, name is Methyl 5-hydroxy-1-methyl-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H8N2O3

6. 5-Difluoromethoxy-3-methoxycarbonyl-1-methylpyrazole 67.6 g (0.43 mol) 5-Hydroxy-3-methoxycarbonyl-1-methylpyrazole and 299.2 g (2.17 mol) potassium carbonate was dissolved in 1500 ml dimethylformamide and heated to 70° C. At this temperature chlorodifluoromethane was introduced over 2 hours and the mixture stirred at 80° C. for 1.5 hours. The reaction mixture was added to water and extracted 6 times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The reaction solution was concentrated. Yield: 80.6 g=90.3percent of theory.

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; Hoechst Schering AgrEvo GmbH; US5580986; (1996); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

151521-49-2, name is 4-Isopropyl-1H-pyrazol-5-amine, 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. Computed Properties of C6H11N3

A mixture of diethyl 2-(ethoxymethylene)propanedioate (621.89 mg, 2.88 mmol, 581.21 L, 1 eq), 4-isopropyl-1H-pyrazol-5-amine (400 mg, 2.88 mmol, 1 eq) in AcOH (3 mL) was degassed and purged with N2 for 3 times. The mixture was stirred at 120 C for 2 h under N2; atmosphere. The reaction mixture was cooled to 0 C and filtered. The solid was washed with ethanol and petroleum ether and dried under reduced pressure to give ethyl 7-hydroxy-3-isopropyl-pyrazolo[l,5- a]pyrimidine-6-carboxylate (700 mg, 2.65 mmol, 92.3% yield, 94.5% purity) as a white solid which was used in the next step without further purification. NMR (400 MHz, CD3OD) delta ppm 8.55 (s, 1H), 7.91 (s, 1H), 4.34 (q, J = 7.2 Hz, 2H), 3.11 (m, 1H), 1.40-1.31 (m, 9H); ES-LCMS m/z 250.2 [M+H].

The synthetic route of 151521-49-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYN THERAPEUTICS; CASTRO, Alfredo C.; EVANS, Catherine Anne; (632 pag.)WO2018/195397; (2018); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

4054-67-5, name is 3,3′,5,5′-Tetramethyl-1H,1’H-4,4′-bipyrazole, 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: 4054-67-5

A mixture of Co(CH3COO)2·4H2O (0.050 g, 0.20 mmol), H2bpdc (0.072 g, 0.30 mmol) and H2bpz (0.038 g, 0.20 mmol) in DMF (5 mL) and CH3CN (5 mL) was placed in a Teflon-lined stainless steel vessel (15 mL). The vessel was heated at 140 C for 72 h, then slowly cooled to room temperature. The purple crystals of 1 were isolated by filtrating, washing with DMF, and dried in vacuo. Yield: 24 mg (23.4%). Anal. Calcd for C44H54Co2N6O15: C, 51.57; H, 5.31; N, 8.20%. Found: C, 51.45; H, 5.17; N, 8.11%. IR (KBr, cm-1): 3426(vs), 2919(w), 1680(s), 1605(s), 1540(m), 1394(s), 1297(m), 1172(w), 1130(w), 851(m), 765(s).

The synthetic route of 4054-67-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jia, Li-Na; Zhao, Yang; Hou, Lei; Cui, Lin; Wang, Hai-Hua; Wang, Yao-Yu; Journal of Solid State Chemistry; vol. 210; (2014); p. 251 – 255;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 151049-87-5, name is 3-Bromo-1-methyl-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 151049-87-5, name: 3-Bromo-1-methyl-1H-pyrazole

To a solution of 3-bromo-1-methyl-1H-pyrazole (650 mg, 4.O4mmol) in acetonitrile(10 mL) was added 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octanebis(tetrafluoroborate) (2.15 g, 6.06 mmol). The mixture wasstirred room temperature for 72 h. The reaction was concentrated in vacuo and the residue was dissolved in ethyl acetate (20 mL), washed with saturated sodium bicarbonate (20 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified via flash silica chromatography (solvent gradient: 0-2% ethyl acetate in petroleum ether) to yield 150 mg crude of the title compound as a white 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; GENENTECH, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; BRAUN, Marie-Gabrielle; GIBBONS, Paul; LEE, Wendy; LY, Cuong; RUDOLPH, Joachim; SCHWARZ, Jacob; ASHKENAZI, Avi; FU, Leo; LAI, Tommy; WANG, Fei; BEVERIDGE, Ramsay; ZHAO, Liang; (652 pag.)WO2018/166528; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 285984-25-0, 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. 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of compounds 10a-d or compounds 17a-d (1.0 mmol) in dichloromethane (10 mL) was slowly added to a stirred solution of triphosgene (109 mg, 0.36 mmol) in dichloromethane (50 mL) over a period of 30 min using a syringe. After stirring for a further 30 min, a solution of compound 25a-r (0.6 mmol) and triethylamine (0.4 mL, 2.77 mmol) in dichloromethane (10 mL) was added in one portion. The reaction mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction was poured into water (50 mL) and extracted three times with dichloromethane. The organic layer was washed with water (5 mL), sat. NaCl solution (5 mL), anddried over Na2SO4. After evaporation of solvent under vacuum, the residue was purified by silica gel chromatography to give the desired chromanylurea or 2H-chromenyl urea compounds.

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-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Xingzhou; Zhou, Xinming; Zhang, Jing; Wang, Lili; Long, Long; Zheng, Zhibing; Li, Song; Zhong, Wu; Molecules; vol. 19; 2; (2014); p. 2004 – 2028;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 852443-61-9, name is 3-(Trifluoromethyl)-1H-pyrazol-5-amine, molecular formula is C4H4F3N3, 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: 852443-61-9

N,N-DIISOPROPYLETHYLAMINE (0.022 ml, 0.126 mmol) was added to the mixture of the 3-(TRIFLUOROMETHYL)-1H-PYRAZOL-5-AMINE (19.01 mg, 0.126 mmol), HATU (47.8 mg, 0.126 mmol), lithium 4-(8-amino-3-((6R,8aS)-3-oxooctahydroindolizin-6-yl)imidazo[1,5-a]pyrazin-1-yl)benzoate (Intermediate 20) (50 mg, 0.126 mmol) in DMF (2 ml) and stirred for 30 min. at 0 C. LC-MS shows completion of the reaction. Product was separated on flash LC on 12 g column (13:10% MeOH, 0.1% NH3OH in CH2Cl2/A: CH2Cl2 (gradient from 0% B to 40% B) to give 4-(8-amino-3-((6R,8aS)-3-oxooctahydroindolizin-6-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(3-(trifluoromethyl)-1H-pyrazol-5-yl)benzamide (14.3 mg, 0.027 mmol, 21.67% yield.): LC-MS: LC-MS method A, RET. TIME=2.41 min., MS found (M)+ m/z=525.26.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 852443-61-9, its application will become more common.

Reference:
Patent; KIM, RONALD M.; Liu, Jian; Gao, Xiaolei; Boga, Sobhana Babu; Guiadeen, Deodialsingh; Kozlowski, Joseph A.; Yu, Wensheng; Anand, Rajan; Yu, Younong; Selyutin, Oleg B.; Gao, Ying-Duo; Wu, Hao; Liu, Shilan; Yang, Chundao; Wang, Hongjian; US2014/206681; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

37622-90-5, name is Ethyl 4-pyrazolecarboxylate, 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. Quality Control of Ethyl 4-pyrazolecarboxylate

[1326] to a solution of ethyl 1H-pyrazole-4-carboxylate (5 g, 35.68 mmol) and Cs2CO3 (23.25 g, 71.36 mmol) in DMF(100 ml) was added mel (10.13 g, 71.36 mmol, 4.44 ml). The mixture was stirred at 25c for 16h. The mixture was filtered, the filtrate was diluted with H2O (500 ml), extracted with ea (50 ml x 3), dried over Na2SO4, filtered and concentrated to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 5/1). Compound 282a (4.5 g, yield: 81.81%) was obtained as a yellow oil. 1H NMR (400mhz, CDCl3) delta 7.84 (d, = 8.5 hz, 2h), 4.24 (q, = 7.3 hz, 2h), 4.03-3.70 (m, 3h), 1.30 (t, j = 7.2 hz, 3h). MS (ESI) m/z (M+H)+155.0.

The synthetic route of 37622-90-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); 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. 75415-03-1, name is 2-(1H-Pyrazol-3-yl)pyridine, A new synthetic method of this compound is introduced below., name: 2-(1H-Pyrazol-3-yl)pyridine

EXAMPLE 12 The synthesis of 1,3-di(2-pyridyl)pyrazole (13). A mixture of compound 11 (22.2 g, 153 mmol) and 2-bromopyridine (42.3 g, 268 mmol) was heated for 20 h at 190 C. The cooled mixture was dissolved in hot H2 O (200 ml) and the pH was adjusted to basic with solid Na2 CO3. After cooling, the precipitate was filtered and washed with cold H2 O. Yield: 32.9 g (97%). UV (EtOH): 294, 283, 224. IR (KBr): 1593, 1578 (arom). 1 H-NMR (CDCl3): 7.14 (d, J=2.6, 1H); 7.21 (ddd, J=1.0, 4.9, 7.3, 1H); 7.27 (ddd, J=1.1, 4.9, 7.3, 1H); 7.79 (dt, J=1.7, 7.3, 1H); 7.85 (dt, J=1.7, 7.3, 1H); 8.12-8.16 (m, 2H); 8.44 (dd, J=1.7, 4.9, 1H); 8.64 (d, J=2.6, 1H); 8.68 (bd, J=4.9, 1H).

The synthetic route of 75415-03-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wallac Oy; US5859215; (1999); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, 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. COA of Formula: C14H19N3

Intermediate B: Phenyl (3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)carbamate A solution of 3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-amine (Intermediate A) (20 g, 87.0 mmol) in isopropyl acetate (240 mL) was added to a stirred solution of sodium carbonate (11.3 g, 106 mmol) in water (80 mL). After 10 min phenyl chloroformate (12.1 mL, 96 mmol) was added and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with water (160 mL), the layers were separated and the organics were washed with water (2*80 mL), brine (80 mL), dried (MgSO4) and concentrated in vacuo. The resulting yellow solid was suspended in 10% ether/iso-hexane (320 mL) and stirred until a uniform suspension was obtained. The solid was collected by filtration and washed with iso-hexane to yield the subtitle compound phenyl (3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)carbamate as a white powder (27.3 g, 88%); Rt 2.65 min (Method 1); m/z 350 (M+H)+ (ES+); 1H NMR delta:1.29 (9H, s), 2.37 (3H, s), 6.35 (1H, s), 7.10-7.23 (3H, overlapping m), 7.33-7.46 (6H, overlapping m), 9.99 (1H, s).

The synthetic route of 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RESPIVERT LTD; TOPIVERT PHARMA LTD.; LONGSHAW, ALISTAIR IAN; FORDYCE, EUAN ALEXANDER FRASER; ONIONS, STUART THOMAS; KING-UNDERWOOD, JOHN; VENABLE, JENNIFER; US2015/232450; (2015); 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, Product Details of 288-13-1

To a solution of 1H-pyrazole (5.00 g) in toluene (67.0 mL) were added dimethylsulfamoyl chloride (7.89 mL) and triethylamine (13.3 mL) at room temperature, and the reaction mixture was stirred at room temperature for 18 hr. The resulting solid was removed by filtration, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.24 g). 1H NMR (400 MHz, CDCl3) delta 2.91 (6H, s), 6.38 (1H, dd, J = 2.6, 1.8 Hz), 7.72 (1H, d, J = 1.2 Hz), 7.96 (1H, d, J = 2.4 Hz)

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; NAGAMIYA, Hiroyuki; YOSHIDA, Masato; SETO, Masaki; MARUI, Shogo; ODA, Tsuneo; ISHICHI, Yuji; SUZUKI, Hideo; KUSUMOTO, Tomokazu; YOGO, Takatoshi; RHIM, Chul Yun; YOON, Cheolhwan; LEE, Gil Nam; KANG, Hyun Bin; KIM, Kwang Ok; JEON, Hye Sun; EP2818473; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics