Tag: M.W:100-200

Reference of 637336-53-9,Some common heterocyclic compound, 637336-53-9, name is Methyl 4-amino-1-methyl-1H-pyrazole-3-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.

Synthesis of Compound 32.6 [0287] To a solution of 32.5 (250 mg, 0.5 mmol, 1.0 eq) in DMF (5 mL) were added methyl 4-amino-l-methyl-lH-pyrazole-3-carboxylate (155 mg, 1.0 mmol, 2.0 eq), HBTU (190 mg, 0.5 mmol, 1.0 eq) and DIPEA (130 mg, 1.1 mmol, 2.0 eq). The reaction was stirred at room temperature for 2 h, diluted with EA (100 mL). The mixture was washed with water (30 mL x 3), brine (50 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by prep-TLC (PE : EA = 1 : 1) to give 32.6 (100 mg, yield: 31%) as a red oil. 1H NMR (400 MHz, DMSO- 6) D delta: 10.29 (s, 1H), 9.07 (s, 1H), 8.61 (d, J = 5.2 Hz, 1H), 8.43 (s, 1H), 8.32 (s, 1H), 7.65 (d, J = 4.8 Hz, 1H), 6.73 (t, J = 5.6 Hz, 1H), 3.96 (s, 3H), 3.93-3.89 (m, 5H), 2.87 (q, J = 6.4 Hz, 2H), 1.60-1.57 (m, 2H), 1.52 (s, 9H), 1.38 (s, 9H), 1.26-1.23 (m, 6H); ESI-MS (M+H) +: 642.0.

The synthetic route of 637336-53-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN IDEC MA INC.; JENKINS, Tracy; VESSELS, Jeffery; WO2014/143672; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 16617-46-2, 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. 16617-46-2, name is 3-Amino-1H-pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Following the procedure described in Example 11 wherein dioxane was used as the solvent instead of tetrahydrofuran and hexane was added instead of water after the reaction was completed, 86percent of the product was obtained with m. p. 183-187 °C Example 13 Following the procedure described in Example 1 wherein hydrobromic acid was used as the catalyst instead of hydrochloric acid, 81percent of the product was obtained with m. p. 184- 188 °C.

The synthetic route of 3-Amino-1H-pyrazole-4-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZENTIVA, A.S.; WO2004/37824; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 57999-06-1,Some common heterocyclic compound, 57999-06-1, name is 4-Phenyl-1H-pyrazol-5-amine, molecular formula is C9H9N3, 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.

[00237] Sodium metal (0.64g, 28mmol) was washed with petrol, and then cut into small pieces. The pieces were added to dry toluene (5ml). More dry toluene (5ml) and EtOAc (3.7ml, 38mmol) were added, followed by ethyl formate (0.64ml, 8mmol) dropwise. The mixture was heated at 5O0C for 20 minutes, then cooled to room temperature and stirred for 30 minutes. Additional ethyl formate (ImI, 12.5mmol) was added dropwise, and the mixture stirred at room temperature for 1 hour. A final batch of ethyl formate (ImI, 12.5mmol) was added dropwise, and the mixture stirred at room temperature overnight. The mixture was then diluted with dry EtOH (200ml), and 4-phenyl-lH-pyrazol-5 -amine (2g, 12.6mmol) was added. The mixture was heated under reflux overnight. The mixture was cooled and concentrated. The solid residue was dissolved in hot water and filtered. The filtrate was acidified with cone. HCl until pHl. The precipitate was then filtered off, washed with ether, and dried in vacuo to yield 1.4g (52.7%) of the title compound. 1H NMR (d6-DMSO): 12.30 (IH, d, J 4.3), 8.23 (IH, s), 7.82 (IH, t, J 7.0), 7.60 (2H, d, J 7.1), 7.46 (2H, d, J 7.9), 7.30 (lH, t, J7.4), 5.79 (IH, d, J7.3).

The synthetic route of 57999-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; WO2010/86040; (2010); 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

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

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

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

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

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

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