Tag: M.W=0-100

Adding a certain compound to certain chemical reactions, such as: 36650-74-5, name is 1H-Pyrazole-3-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 36650-74-5, COA of Formula: C4H3N3

General procedure: The example reported for derivatives 22/23 find general application for all the other N-linked heterocycles. Sodium hydride 60% dispersed in mineral oil was added at 0 C to a solution of 3-(trifluoromethyl)-1H-pyrazole in dry DMF. The mixture was stirred at this temperature for 15 min, then for an additional 5 min at room temperature. A solution of derivative 45 in dry DMF (2 ml) was then added and the mixture was stirred at 50 C for 3 h 30 min. After cooling to RT, a saturated NH4Cl solution was added and the mixture was extracted with Et2O (2×). The organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by Silica gel flash chromatography (gradient ethyl acetate in cyclohexane from 5 to 40%) to give the intermediate BOC protected compound 22 and the intermediate BOC protected compound 23.

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-3-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Micheli, Fabrizio; Cavanni, Paolo; Bettati, Michela; Bonanomi, Giorgio; Di Fabio, Romano; Fazzolari, Elettra; Marchioro, Carla; Roscic, Maja; Tarsi, Luca; Visentini, Filippo; Zonzini, Laura; Worby, Angela; Bioorganic and Medicinal Chemistry; vol. 19; 11; (2011); p. 3451 – 3461;,
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. 1453-58-3, name is 3-Methylpyrazole, A new synthetic method of this compound is introduced below., Product Details of 1453-58-3

REFERENCE EXAMPLE 93; Methyl 4-(3-methyl-pyrazol-1-yl)-2-trifluoromethyl-benzoate; Step b) Methyl 4-(3-methyl-pyrazol-1-yl)-2-trifluoromethyl-benzoate: A suspension of hexane washed 60percent sodium hydride (3.85 g) in dry dimethylformamide (150 ml) was treated with the dropwise addition of a solution of 3-methylpyrazole (7.75 ml) in dimethylformamide (50 ml) under nitrogen at room temperature. Stirring was continueduntil the gas evolution subsided (10 minutes). A solution of methyl 4-fluoro-2-trifluoromethylbenzoate (17.8 g) fromstep a) in dimethylformamide (50 ml) was added dropwise to the clear solution. After stirring for 30 min. at room temperature the reaction was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic extracts (3x) were dried over anhydrous sodium sulfate and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (Merck 60) with a dichloromethane-hexane gradient (50percent – 75percent) to give 13.6 g of the title product as a colorless solid. m.p. 59-61°C MS (EI, m/z): 284 (M)+.

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; Wyeth; EP1000062; (2004); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1192-21-8, name is 1-Methyl-1H-pyrazol-5-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 1192-21-8, Recommanded Product: 1-Methyl-1H-pyrazol-5-amine

(3 S)-7-(2-Chloro-5-methylpyrimidin-4-yl)-3-methyl-2-((2-methylpyridin-3-yl)methyl)-3 ,4- dihydropyrrolo [1 ,2-a]pyrazin- 1 (2H)-one (118 mg, 0.31 mmol), i-methyl-i H-pyrazol-5 -amine (33.0 mg, 0.34 mmol), cesium carbonate (201 mg, 0.62 mmol) and BrettPhos 3rd generation pre-catalyst (14.01 mg, 0.02 mmol) were suspended in tert-butanol (5 mL) and de-gassed for 10 minutes. The reaction was heated to 80 °C for 18 hours under nitrogen. The mixture was cooled to room temperature, diluted with EtOAc (50 mL), washed with saturated aqueous sodium bicarbonate (10 mL) and the layers separated. The aqueousportion was washed with ethyl acetate (50 mL) and the combined organics were dried (sodium sulfate) and concentrated in vacuo to a brown gum (198 mg). The solid was taken up in DMSO (5 mL) and filtered. The crude product was 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 (3 S)-3 -methyl-7-(5 -methyl-2-(( i-methyl-i H-pyrazol-5 -yl)amino)pyrimidin-4-yl)-2-((2-methylpyridin-3 -yl)methyl)-3 ,4-dihydropyrrolo [1 ,2-a]pyrazin- 1 (2H)-one (74.0 mg,54.1 percent) as a white solid. ?H NMR (400 MHz, DMSO, 30 °C) 1.14 (3H, d), 2.32 (3H, s),3.68 (3H, s), 3.81 (1H, d), 4.16 – 4.27 (2H, m), 4.34 (1H, dd), 5.12 (1H, d), 6.26 (1H, d),7.20 (1H, dd), 7.27 (1H, d), 7.33 (1H, d), 7.58 – 7.7 (2H, m), 8.23 (1H, s), 8.35 (1H, d),9.06 (1H, s). mlz: ES+ [M+H]+ 442.

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; 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: 1192-21-8, name is 1-Methyl-1H-pyrazol-5-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 1192-21-8, COA of Formula: C4H7N3

Under nitrogen a solution of methyl 4-bromo-l-(3-methoxyphenyl)-lH-pyrazole-3- carboxylate (600 mg, 1.928 mmol, 1.00 equiv), l-methyl-lH-pyrazol-5-amine (563 mg, 5.797 mmol, 1.00 equiv), t-BuXPhos (82 mg, 0.193 mmol, 0.10 equiv), 3rd Generation t-BuXPhos precatalyst (154 mg, 0.194 mmol, 0.10 equiv), t-BuONa (279 mg, 2.903 mmol, 1.50 equiv) in 1 ,4-dioxane (12 mL) was irradiated with microwave radiation for 90 min at 90 °C. The resulting solution was concentrated under vacuum and the residue was purified by a silica gel column chromatography eluted with dichloromethane/methanol (1 : 1) to give the title compound (425 mg, 70percent) as a yellow solid. LC-MS (ES, m/z): 314 [M+H]+.

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-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; CASTANEDO, Georgette; FENG, Jianwen A.; CRAWFORD, James John; LEE, Wendy; LIN, Xingyu; HU, Baihua; WU, Guosheng; (218 pag.)WO2016/135163; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, 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 35344-95-7, COA of Formula: C4H4N2O

1-isopropyl-1H-pyrazole-4-carbaldehyde To a solution of lH-pyrazole-4-carbaldehyde (2.0 g, 21 mmol) and 2-iodopropane (5.32 g, 31.5 mmol) in DMF (10 mL) was added sodium hydride (60% dispersion in mineral oil, 0.83 g, 20.7 mmol) in one portion. The resulting mixture was stirred at room temperature for 2 hours, before being quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 0-50% EtO Ac/heptane to obtain 1- isopropylpyrazole-4-carbaldehyde (1.2 g, 42% yield). 1H NMR (400 MHz, CDC13) delta 9.86 (s, 1H), 7.97 (s, 2H), 4.54 (p, / = 6.7 Hz, 1H), 1.55 (d, / = 6.7 Hz, 6H).

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.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian K.; GEHLING, Victor S.; HARMANGE, Jean-Christophe; LAI, Tommy; LIANG, Jun; DRAGOVICH, Peter; ORTWINE, Dan; LABADIE, Sharada; ZHANG, Birong; KIEFER, Jim; WO2015/135094; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 31230-17-8, name is 5-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 31230-17-8, Safety of 5-Methyl-1H-pyrazol-3-amine

Step 1: Compound 1a (3.64 g, 20 mmol), 3-amino-5-methyl-pyrazole (1.94 g, 20 mmol) and diisopropylethylamine (5.17 g, 40 mmol) were added to 20 mL of ethanol solution and then stirred at room temperature for 2 days. The insoluble substance was collected to obtain Compound 1b (3.7 g, Yield 76percent), MS [M + 1]+ 244.0.

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

Reference:
Patent; Zhejiang Hisun Pharmaceutical Co. Ltd.; DING, Yili; YANG, Xuan; YAN, Qingyan; BAI, Hua; CAI, Lifeng; SMITH, Kenneth; CHAI, Jian; EP2754659; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25222-43-9, name is (1H-Pyrazol-4-yl)methanol, 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 25222-43-9, Safety of (1H-Pyrazol-4-yl)methanol

Step 1: 4-(tert-Butyl-dimethyl-silanyloxymethyl)-1H-pyrazole (1H-Pyrazol-4-yl)-methanol (368 mg, [CAS Reg. No. 25222-43-9]) was dissolved in DMF (15 mL) and cooled to 0° C. To this solution was added triethylamine (455 mg), 4-dimethylaminopyridine (46 mg) and tert-butyldimethylchlorsilane (678 mg). Stirring was continued for 2 hours at r.t. The reaction mixture was poured into ice and extracted with chloroform. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, heptane:ethyl acetate=100:0 to 0:100, then ethylacetate_methanol=95:5) to give the title compound as a yellow oil (348 mg, 42percent). MS (m/e)=213.3 [MH+].

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

Reference:
Patent; Hunziker, Daniel; Lerner, Christian; Mueller, Werner; Sander, Ulrike Obst; Pflieger, Philippe; Waldmeier, Pius; US2010/249139; (2010); A1;,
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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Methyl-1H-pyrazol-5-amine

(3 S)-7-(2-Chloro-5 -methylpyrimidin-4-yl)-3 -methyl-2-((3 -methylpyrazin-2-yl)methyl)-3 ,4-dihydropyrrolo [1 ,2-a]pyrazin- 1 (2H)-one (125 mg, 0.33 mmol), 1-methyl-i H-pyrazol5-amine (34.9 mg, 0.36 mmol), cesium carbonate (213 mg, 0.65 mmol) and BrettPhos 3rdgeneration pre-catalyst (14.80 mg, 0.02 mmol) were suspended in tert-butanol (5 mL) andde-gassed for 10 minutes. The reaction was heated to 80 °C for 18 hours under nitrogen.The mixture was cooled to room temperature, diluted with EtOAc (50 mL), washed with saturated aqueous sodium bicarbonate (10 mL) and the layers separated. The aqueous portion was washed with ethyl acetate (50 mL) and the combined organics were dried (sodium sulfate) and concentrated in vacuo to a brown gum which was taken up in DMSO(5 mL) and filtered. The crude product was purified by preparative HPLC (Waters XBridge Prep Ci8 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 (3S)-3-methyl-7-(5-methyl-2- ((i-methyl-i H-pyrazol-5 -yl)amino)pyrimidin-4-yl)-2-((3 -methylpyrazin-2-yl)methyl)-3 ,4-dihydropyrrolo[i,2-a]pyrazin-i(2H)-one (97 mg, 67.0 percent) as a white solid. ?H NMR(500 MHz, DMSO, 30 °C) 1.43 (3H, d), 2.58 – 2.6 (3H, m), 2.83 (3H, s), 3.94 (3H, s), 4.15- 4.25 (iH, m), 4.44 (iH, dd), 4.55 – 4.67 (2H, m), 5.60 (iH, d), 6.52 (iH, d), 7.50 (iH, d),7.59 (iH, d), 7.90 (iH, d), 8.49 (iH, d), 8.64 – 8.71 (2H, m), 9.33 (iH, s). mlz: ES+[M+H]+ 443.

According to the analysis of related databases, 1192-21-8, the application of this compound in the production field has become more and more popular.

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

Related Products of 1453-58-3, These common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, 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.

3-Methyl-1H-pyrazole (1 g, 12.18 mmol), phenylboronic acid (3 g, 24.36 mmol) and pyridine (2 mL, 24.36 mmol) were dissolved (160 mL) and Cu(AcO)2 (3.32 g, 18.27 mmol) and molecular sieves were added and mixture was stirred at r.t. for 48 h. Suspension was filtered through Celite and concentrated and the crude thus obtained was purified by normal phase chromatography using hexane/ethyl acetate from 0% to 7.5% to yield the title compound (83% yield). LRMS: m/z 159 (M+1)+ Retention time: 2.83 min (Method B) 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 2.38 (s, 3 H) 6.25 (d, J=2.34 Hz, 1 H) 7.18-7.32 (m, 1 H) 7.42 (t, 2 H) 7.65 (dd, J=8.60, 1.17 Hz, 2 H) 7.81 (d, J=2.34 Hz, 1 H).

Statistics shows that 3-Methylpyrazole is playing an increasingly important role. we look forward to future research findings about 1453-58-3.

Reference:
Patent; Almirall, S.A.; Erra Sola, Montserrat; Aguilar Izquierdo, Nuria; Carrascal Riera, Marta; Taboada Martinez, Lorena; Navarro Romero, Eloisa; Vidal Juan, Bernat; EP2390252; (2011); A1;,
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., name: 1H-Pyrazole-4-carbonitrile

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).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 31108-57-3.

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