Tag: M.W=0-100

Related Products of 35277-02-2, 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. 35277-02-2, name is 4-Fluoro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Synthesis of 5-(4-fluoro-lH-pyrazol-l-yl)pyrazine-2-carbonitrile. (0362) To a solution of 5-chloropyrazine-2-carbonitrile (280 mg, 2.0 mmol) in DMF was added 4-fluoro-lH-pyrazole (170 mg, 2.0 mmol) and potassium acetate (395 mg, 4.0 mmol). The mixture was stirred at 100 C for 4 hours, then cooled to 20 C, poured into brine (25 mL), and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and purified by column chromatography (hexane: ethyl acetate = 5: 1) to give 5-(4-fluoro-lH- pyrazol-l-yl)pyrazine-2-carbonitrile (310 mg, 82%). The structure was confirmed by LC-MS.

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

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason, D.; KIM, Joseph, L.; WILSON, Kevin, J.; WILSON, Douglas; DIPIETRO, Lucian, V.; (84 pag.)WO2017/79140; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 132712-71-1, A common heterocyclic compound, 132712-71-1, name is 3-Methyl-1H-pyrazol-5-ol, molecular formula is C4H6N2O, 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.

General procedure: To a well-stirred solution of isatin and malononitrile(1 mmol each) in ethanol (95%, 4 mL) was added dimedone,4-hydroxycoumarin, 4-hydroxy-N-methylquinolin-2-one,or 2-methyl-pyrazol-2-one [generated in situ from ethylacetoacetate and hydrazine hydrate, 1 mmol each]. To thissolution was added THAM (30 mol %) and stirring wascontinued at ambient temperature. Upon completion of thereaction (TLC), water (5 mL) was added and stirring wascontinued for 10 min more. Resultant solid product wasfiltered, washed repeatedly with water, and dried. The dried solid was washed thrice with hexaneechloroformmixture (1:1, v/v) and dried again. Resultant product didnot require any further purification.

The synthetic route of 132712-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khot, Supriya S.; Anbhule, Prashant V.; Desai, Uday V.; Wadgaonkar, Prakash P.; Comptes Rendus Chimie; vol. 21; 9; (2018); p. 814 – 821;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, 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 C4H4N2O

To a 50-mL round-bottom flask was placed a solution of [( 1 s,3s)-3-(3-pheny 1- 1 ,2-oxazole-5-amido)cyclobuty l]methy 1 4-methylbenzene- 1 -sulfonate ( 1 g, 2.34 mmol, 1.00 equiv) in DMF (15 mL) then Cs2C03 (1.5 g, 4.60 mmol, 2.00 equiv) and lH-pyrazole-4-carbaldehyde (338 mg, 3.52 mmol, 1.50 equiv) were added. The resulting solution was stirred for 3 h at 100°C then the solids were removed by filtration. The crude product was purified by Flash-Prep-HPLC (CombiFlash-1 : Column, C18 silica gel; mobile phase, X: H20 (0.5percent NFUHCC ), Y: ACN, X/Y=90/10 increasing to X/Y=5/95 within 40 min; Detector, UV 254 nm) affording 460 mg (56percent) of 3-phenyl-N-[(l s,3s)-3-[(4-formyl-lH- pyrazol-l-yl)methyl]cyclobutyl]-l,2-oxazole-5-carboxamide as a yellow solid. LCMS (ES, m/z): [M+H]+ = 351.1.

The synthetic route of 35344-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (194 pag.)WO2016/105485; (2016); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, 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 1904-31-0, name: 1-Methyl-1H-pyrazol-3-amine

(E)-Cyclopentyloxyimino-(3,4-dichloro-phenyl)-acetic acid (100 mg, 0.33 mmol) was dissolved in methylene chloride (1.6 mL). N,N-diisopropylethylamine (173 muL, 0.99 mmol) and 1-methyl-1H-pyrazol-3-ylamine (32 muL, 0.33 mmol) were added and the reaction mixture was cooled to 0° C. O-(7-Azabenzotriazole-1-yl)-N,N,N’N’-tetramethyluronium hexafluorophosphate (126 mg, 0.33 mmol) was added and the reaction mixture was allowed to warm to 25° C. After stirring 16 h, the reaction mixture was diluted with chloroform (2 mL) and washed with saturated aqueous sodium bicarbonate solution (1.5 mL). The aqueous phase was extracted with chloroform (1.5 mL) and the combined organic phases were filtered through sodium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (Merck silica gel 60, 40-63 mum; 40percent ethyl acetate/hexanes) to afford (E)-2-cyclopentyloxyimino-2-(3,4-dichloro-phenyl)-N-(1-methyl-1H-pyrazol-3-yl)-acetamide (103 mg, 82percent) as a white solid after lyophilization from aqueous dioxane: LC-MS (ESI) m/e calcd for C17H18Cl2N4O2 [M+] 380.08, found 381 [M+H+]; H1-NMR (400 MHz, CDCl3) .box. ppm 1.64 (m, 4 H, 2*CH2), 1.85 (m, 4 H, 2*CH2), 3.83 (s, 3 H, NCH3), 4.84 (m, 1 H, OCH), 6.70 (d, J=2.3 Hz, 1 H, Ar), 7.26 (d, J=2.3 Hz, 1 H, Ar), 7.33 (dd, Jo=8.3, Jm=1.9 Hz, 1 H, Ar), 7.47 (d, Jo=8.3 Hz, 1 H, Ar), 7.61 (d, Jm=1.9 Hz, 1 H, Ar), 9.15 (s, 1 H, NH).

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, 1-Methyl-1H-pyrazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Berthel, Steven Joseph; Kester, Robert Francis; Murphy, Douglas Eric; Prins, Thomas Jay; Ruebsam, Frank; Tran, Chinh Viet; Vourloumis, Dionisios; US2008/146625; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 28466-26-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 28466-26-4 name is 4-Aminopyrazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[00606] Synthesis of compound 1-78. Compound 1-78 was prepared from compounds 3.4 and 96.2 using protocol described in Example 94. . LCMS (ES, m/z): 440 [M+H]+; 1H-NMR (300 MHz, DMSO) delta 8.87 (1H, s), 7.82 (1H, brs), 7.52 (1H, brs), 5.71 (1H, d), 4.05-3.89 (1H, m), 3.58 (4H, brs), 3.01-2.95 (2H, m), 2.84-2.79 (2H, m), 2.50 (4H, m), 2.42-2.34 (2H, m), 2.26- 2.18 (1H, m), 2.05 (2H, d), 1.92 (2H, d), 1.47-1.30 (4H, m). [00599] Example 94. Synthesis of 2-(4-((4-(((lr,4r)-4-morpholinocyclohexyl)amino)-6,7- dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-2-yl)amino)-lH-pyrazol-l-yl)acetate, Example 1-76 [00600] To a solution of intermediate 3.4 (50 mg, 0.13 mmol, 1.00 equiv) and 2-(4-amino- lH-pyrazol-l-yl)acetic acid (36 mg, 0.26 mmol, 2.00 equiv) in isopropanol (5 mL) was added hydrochloric acid (4 M in dioxane, 0.1 mL) at room temperature. The reaction was stirred for 2 h at 140 C and irradiated in microwave. The resulting mixture was concentrated under vacuum and resulting crude was purified to yield compound 1-76 as a yellow solid. LCMS (ES, m/z) 540 [M+H]+. 1H NMR (300 MHz, d6-OMSO, ppm): delta 8.99 (s, 1H), 7.90 (s, 1H), 7.51 (s, 1H), 7.26-7.06 (m, 1H), 5.79-5.71 (m, 1H), 4.99-4.91 (m, 3H), 4.01-3.99 (m, 1H), 3.77-51 (m, 4H), 3.05-2.98 (m, 2H), 2.83-2.73 (m, 2H), 2.61-2.53 (m, 5H), 2.40-2.35 (m, 2H), 2.01-1.94 (m, 2H), 1.49-1.35 (m, 4H), 1.20-1.15 (m, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Aminopyrazole, and friends who are interested can also refer to it.

Reference:
Patent; NIMBUS IRIS, INC.; CHAUDHARY, Divya; KAPELLER-LIBERMANN, Rosana; WO2014/194242; (2014); A2;,
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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 31108-57-3

To a solution of A26 (300mg, 729 umol, 1.00 Eq) in acetone (5 mL) was added K2CO3 (200 mg, 1.45 mmol, 2.0 Eq) and 1H-pyrazole -4-carbonitrile (81.3 mg, 874 umol, 1.2 Eq) at 25oC. The reaction mixture was stirred at 25C for 16 hrs. Then, TLC showed the material was disappeared. The mixture was diluted with water (20 mL) and extracted with EA (30 mL×2). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated in vacuum. The residue was purified by silica gel chromatography( 100-200 mesh silica gel, petroleum ether/ethyl acetate =2/1) to afford A39 (245 mg, 549 umol) as a off-white solid. 1H NMR (A39): 400MHz delta 7.86 (s, 1H), 7.81 (s, 1H), 5.04-4.88 (m, 2H), 2.62-2.58 (m, 1H), 0.95 (s, 3H), 0.65 (s, 3H).

According to the analysis of related databases, 31108-57-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAGE THERAPEUTICS, INC.; MARTINEZ BOTELLA, Gabriel; SALITURO, Francesco, G.; ROBICHAUD, Albert, Jean; HARRISON, Boyd, L.; (275 pag.)WO2016/61527; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1453-58-3, A common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, molecular formula is C4H6N2, 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.

A stirred solution of 3-methylpyrazole (82.1 g, 1.0 mol) in water (3.5 L) was heated to 70 °C. Potassium permanganate (111 g, 0.70 mol) was added in one portion, keeping the temperature near 70 °C. The reaction mixture was stirred for 1 h at 70 °C, and then a second portion of potassium permanganate (111 g) was added at 70 °C. After 1 h, a final portion of potassium permanganate (111 g) was added at 70 °C. The reaction mixture was stirred a further 2 h at 70 °C, and any unreacted oxidant was reduced by the dropwise addition of isopropanol. The reaction mixture was cooled to room temperature, filtered, the solid was rinsed with water, and the filtrate evaporated to 500 ML. The aqueous was chilled to 0 °C, acidified with concentrated HCI, filtered, the solid product washed with water, and dried under vacuum to provide pyrazole- 3-carboxylic acid as a white solid (64.4 g, 57percent).

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; MERCK & CO., INC.; WO2004/58702; (2004); 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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., Safety of 1-Methyl-1H-pyrazol-5-amine

(S)-7-(2-chloro-5-methylpyrimidin-4-yl)-3-methyl-2-((2-methyl-2H- 1 ,2,3-triazol-4- yl)methyl)-3 ,4-dihydropyrrolo [1 ,2-a]pyrazin- 1 (211)-one (190 mg, 0.51 mmol), 1-methyl- 1H-pyrazol-5-amine (54.6 mg, 0.56 mmol), cesium carbonate (333 mg, 1.02 mmol) and BrettPhos 3rd generation pre-catalyst (23.16 mg, 0.03 mmol) were suspended in tertbutanol (6mL) and de-gassed for 10 minutes. The reaction was heated to 80 °C for 18hours under nitrogen. Reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate (25 mL), dried over sodium sulfate and concentrated in vacuo to give a yellow solid. The crude product was dissolved in DMSO (5 mL), filtered and purified by preparative HPLC (Waters XBridge Prep C18 OBD column, Sji silica, 30 mm diameter, 100 mm length),using decreasingly polar mixtures of water (containing 1percent NH3) and MeCN as eluents.Fractions containing the desired compound were evaporated to dryness to afford (S)-3-methyl-7-(5 -methyl-2-(( 1-methyl-i H-pyrazol-5 -yl)amino)pyrimidin-4-yl)-2-((2-methyl-2H- 1,2,3 -triazol-4-yl)methyl)-3 ,4-dihydropyrrolo [1 ,2-a]pyrazin- 1 (211)-one (102 mg, 46.2percent) as a white solid. ?H NMR (500 MHz, DMSO, 30 °C) 1.15 (3H, d), 2.33 (3H, s), 3.70(3H, s), 3.9 – 4.01 (1H, m), 4.12 (3H, d), 4.14 – 4.32 (2H, m), 4.35 (1H, d), 5.08 (1H, d),6.27 (1H, d), 7.26 (1H, d), 7.34 (1H, d), 7.64 (1H, d), 7.69 (1H, s), 8.24 (1H, s), 9.08 (1H,s). mlz: ES+ [M+H]+ = 433.

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; ASTRAZENECA AB; WARD, Richard, Andrew; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 31108-57-3, name is 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 31108-57-3, SDS of cas: 31108-57-3

General procedure: The appropriate carboxylic acid (1.0 equiv) was treated with oxalylchloride (1.1 equiv) in CH2Cl2 (0.5 M) at 0 C. The reaction mixture wasstirred at room temperature for 1 h. The solvent was removed under N2and the acid chloride (1 equiv) was dissolved in anhydrous CH2Cl2(0.5 M). The appropriate pyrazole (1.0 equiv) was dissolved in CH2Cl2(0.5 M) and cooled to 0 C. The acid chloride (1 equiv) in CH2Cl2 (0.5 M) was added dropwise and the reaction mixture was stirred atroom temperature for 3 h. The mixture was diluted with EtOAc, washedwith saturated aqueous NaCl, and dried over Na2SO4. Evaporationunder reduced pressure yielded the crude product that was purified byflash chromatography (SiO2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Pyrazole-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Otrubova, Katerina; Chatterjee, Shreyosree; Ghimire, Srijana; Cravatt, Benjamin F.; Boger, Dale L.; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1693 – 1703;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 930-36-9,Some common heterocyclic compound, 930-36-9, name is 1-Methylpyrazole, molecular formula is C4H6N2, 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.

S1, under nitrogen atmosphere protection,100g of 1-methylpyrazole was added to 2L of tetrahydrofuran, stirred to dissolve to uniform state,Then cooled to minus 60 degrees,Then 2.5M concentration of n-butyllithium 600ml,Insulation below minus 60 degrees Celsius,After the addition of n-butyl lithium is completed, and then incubated 0.4h,Cooled to minus 65 degrees Celsius,100 mL of N, N-dimethylformamide was added dropwise,After dropping N, N-dimethylformamide overnight at room temperature,The whole was cooled to 0 degrees Celsius, 300ml deionized water was added dropwise after quenching.S2, extracted with 500 ml of ethyl acetate each time,Repeat 2 times to separate the organic phase,Each time with 500ml saturated brine wash,Repeat washing 2 times, with 50g anhydrous sodium sulfate drying 1h,Suction filtration, then decompression rotary steaming,The product from S2 step is 1-methyl-1H-pyrazole-5-carbaldehyde.

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

Reference:
Patent; Beijing Luhe Ningyuan Technology Co., Ltd.; Jiang Yongjun; Xing Lixin; Liu Bo; (11 pag.)CN106928143; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics