Day: May 27, 2021

Electric Literature of 50877-42-4,Some common heterocyclic compound, 50877-42-4, name is 1-Benzyl-4-iodo-1H-pyrazole, molecular formula is C10H9IN2, 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.

To a solution of 4-[7-(1-ethylpropyl)-5-(4-fluorophenyl)furo[3,2-b]pyridine-2-carbonyl]- 3,3-dimethyl-piperazin-2-one (70 mg, 0.160 mmol) in DMF (1.750 mL) were added 1- benzyl-4-iodo-pyrazole (68.18 mg, 0.240 mmol), CuI (15.23 mg, 0.080 mmol) and K3PO4 (67.93 mg, 0.320 mmol). The mixture was degassed for 10 min, then to it was added N,N’-dimethylethane-1,2-diamine (14 mg, 16.91 muL, 0.159 mmol). The mixture was allowed to stir overnight at 100C. The suspension was cooled down, water was added along with EtOAc. The phases were separated to afford a crude mixture of 1-(1- benzylpyrazol-4-yl)-4-[7-(1-ethylpropyl)-5-(4-fluorophenyl)furo[3,2-b]pyridine-2- carbonyl]-3,3-dimethyl-piperazin-2-one (95.0 mg, 100.0%)

The synthetic route of 50877-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; SAYEGH, Camil Elie; STURINO, Claudio; FOURNIER, Pierre-Andre; LACOSTE, Jean-Eric; DIETRICH, Evelyne; MARTEL, Julien; VALLEE, Frederic; (494 pag.)WO2016/154075; (2016); 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. 78703-53-4, name is 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., Safety of 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid

General procedure: Pyrazole acid chlorides 6a-b were prepared by refluxing 4a-b in thionyl chloride for 8 h. Pyrazole acid chlorides 6a-b (12 mmol) in anhydrous tetrahydrofuran (THF; 30 mL) were slowly added to a solution of amine derivatives or 5-methylisoxazol-3-ol (10 mmol) and K2CO3 (1.38 g, 10 mmol) in anhydrous THF (30 mL) at a controlled temperature of 5 C. The reaction proceeded at room temperature until 6a-b was no longer tested by TLC. The reaction solution was then filtered and the solvent distilled. The residue was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate and recrystallized to generate the target pyrazole carboxamides and isoxazolol pyrazole carboxylates (7aa-bk). The product yields ranged from 40% to 80%. All 20 compounds were novel, and the physical and spectral data for these compounds are listed below.

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; Sun, Jialong; Zhou, Yuanming; Molecules; vol. 20; 3; (2015); p. 4383 – 4394;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5334-39-4, name is 3-Methyl-4-nitro-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 5334-39-4, Recommanded Product: 5334-39-4

To a solution of 3 -methyl -4-nitro-lH-pyrazole (5 g, 39.34 mmol) in DMF (50 rnL) was added NaH (1.89 g, 47.21 mmol, 60% purity) at 0 C under N2. The mixture was stirred at 20 C for 1 h, then added with ethyl 2-chloropropanoate (10.75 g, 78.68 mmol, 10.05 mL) and stirred for 15 h. The mixture was poured into ice water (250 mL). The aqueous phase was extracted with EtOAc (3 chi 100 mL). The combined organic phase was washed with brine (3 chi 100 mL), dried over anhydrous NaaS&t, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE:EtOAc = 2: 1), to give a mixture of ethyl 2-(5-methyi-4-nitro-pyrazoi-l-yl)propanoate and ethyl 2-(3- methyl-4-nitro-pyrazol-l-yl)propanoate as a yellow oil LCMS: RT 0.745 min, m/z = 228.2 [M+H]+ To a mixture of ethyl 2-(5-methyl-4-nitro-pyrazol-l -yl)propanoate and ethyl 2-(3-methyl-4-nitro- pyrazol-l-yl)propanoate (9.3 g, 40.93 mmol) in MeOH (90 mL) was added NaBH4 (3.87 g, 102.33 mmol) at 0 C under N2. The mixture was stirred at 0 C for 2 h. The mixture was concentrated under reduced pressure and purified by silica gel column chromatography (PE:EtOAc = 3: 1), to give a mixture of 2-(5- methyl-4-nitro-pyrazol- l-yl)propan-l -ol and 2-(3-methyl-4-nitro-pyrazol-l-y])propan-l-ol was obtained as a yellow solid. LCMS: RT 0.707 mm, m/z = 222.1 [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, 3-Methyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); 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. 14521-80-3, name is 3-Bromo-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C3H3BrN2

Reference Production Example 4; (1) A mixture of 10.7 g of 3-bromo-1H-pyrazole, 11.8 g of 2,3-dichloropyridine, 57.3 g of cesium carbonate and 80 ml of N,N-dimethylformamide was stirred at 100C for 8 hours. After the reaction mixture was cooled to room temperature, water was poured into the reaction mixture. The reaction mixture was extracted twice with methyl tert-butyl ether. The organic layers were combined, washed sequentially with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 12.9 g of 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine. 2-(3-Bromo-1H-pyrazol-1-yl)-3-chloropyridine 1H-NMR (CDCl3, TMS) delta (ppm): 6.51 (1H, d, J=2Hz), 7.31 (1H, dd, J=8Hz, 4Hz), 7.91 (1H, dd, J=8Hz, 1Hz), 8.04 (1H, d, J=2Hz), 8.45 (1H, dd, J=4Hz, 1Hz)

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 14521-80-3.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2143720; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 5334-39-4, 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. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 3-methyl-4-nitro-lH-pyrazole (5 g, 39.34 mmol) and tetrahydropyran-4-ol (4.82 g, 47.21 mmol, 4.73 mL) in THF (70 mL) was added PI3 (15.48 g, 59.01 mmol) and DIAD (11.93 g, 59.01 mmol . 1.47 mL) in one portion at 0C under N2. The mixture was stirred at 0 C for 60 min, then warmed to 25 C and stirred for 16 h. The mixture was poured into the mixture of PE and EtOAc (PE:Ei()Ac = 1 : 1) (100 mL), filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE:EtOAc = 5: 1) to afford 5- methyl-4-iiitro-l-tetrahydropyran-4-yl-pyrazole and 3-methyl-4-nitro~l -tetrahydro-2H~pyran~4-yl~ pyrazole as yellow solids. LCMS: RT 0.610 min, m/z = 212.2 [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, 3-Methyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); 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. 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., name: 1-Methyl-1H-pyrazol-3-amine

Example 80; 4-Benzyloxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide; To a solution of 4-benzyloxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (77b) (6.98 g, 23.40 mmol) in CH2Cl2 (100 mL) was added thionyl chloride (2.04 mL, 28.1 mmol), followed by 10 drops of DMF. The mixture was refluxed for 2 h, then concentrated and dried under vacuum. The residue was dissolved in CH2Cl2 (100 mL), and 3-amino-1-methyl-pyrazole (2.73 g, 28.1 mmol) was added at 0° C., followed by triethylamine (6.52 ml, 46.80 mmol). The mixture was stirred at 0° C. to room temperature for 1 hr. The reaction was quenched with H2O, extracted with 3.x.CH2Cl2. The combined organic layers were dried over Na2SO4, concentrated and purified by flash column chromatography with 1-3percent MeOH in CHCl3 to give a white solid (5.31 g, 60percent yield). 1H NMR (400 MHz, CDCl3) delta 8.43 (s, 1H) 7.29-7.50 (m, 6H) 7.09 (d, J=1.01 Hz, 1H) 6.84 (dd, J=8.08, 1.77 Hz, 2H) 5.14 (s, 2H) 3.83 (s, 3H) 2.95-3.06 (m, 2H) 1.50 (s, 6H); LCMS for C22H23N3O3 m/z 378.20 (M+H+).

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; Pfizer Inc.; US2008/280875; (2008); 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. 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H14N4O2

To the mixture of 5-amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide (Intermediate P6, 0,301 g, 1,55 mmol) and ethyl (2-chlorophenoxy)-acetate (Intermediate P16, 1.663 g, 7.75 mmol) in dry tetrahydrofuran (16 mL) 5 eq. of IM soLution of potassium tert-butanolate in tetrahydrofuran were addedand the whole was heated at reflux for 18 hours. The crude product was isoLated by extraction with ethyl acetate, organic layer was washed with brine and dried with sodium sulphate. The compound was purified by chromatography on silica gel (hexane/acetone, gradient from 100:0 to 0:100). 95 mg of the titLe product were obtained as an amorphous soLid (yield 29.2%).1H NMR (300MHz, DMSO-d6): delta 12.37(5, 1H), 8.09 (s, 1H), 7.47 (m, 1H), 7.31 (m,1H), 7.25 (m, 1H), 7.01 (m, 1H), 5.14 (s, 2H), 4.87 (m, 1H), 3.94 (m, 2H), 3.47 (m, 2H), 2.09 (m, 2H), 1.77 (m, 2H).MS-ESI: (m/z) calculated for C17H18C1N4O3 [M+H]+: 361 .79, found 361 .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:
Patent; CELON PHARMA S.A.; MOSZCZY?SKI-P?TKOWSKI, Rafa?; BOJARSKI, ?ukasz; STEFANIAK, Filip; WIECZOREK, Maciej; DUBIEL, Krzysztof; LAMPARSKA-PRZYBYSZ, Monika; WO2014/16789; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 131797-35-8, 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. 131797-35-8, name is 5-Chloro-3-(trifluoromethyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of 5-chloro-3-(trifluoromethyl)-lH-pyrazole (i.e. the product of Example 10, Step C) (2.1 g, 12.3 mmol) and potassium carbonate (3.6 g, 26.0 mmol) in 20 mL of Lambdar^-dimethylformamide was added ethyl bromoacetate (2.1 mL, 18.8 mmol), and the resulting mixture was stirred at room temperature for 12 h. The resulting mixture was diluted with ethyl acetate, washed with water, and dried (MgSC^). The reaction mixture was concentrated in vacuo and further purified by medium-pressure liquid chromatography using 0-50% of ethyl acetate in hexanes as eluant to give 940 mg of the title compound as an oil. 1H NMR (CDCl3) delta 1.29 (m, 3 H), 4.27 (q, 2 H), 4.96 (m, 2 H), 6.55 (s, 1 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, 5-Chloro-3-(trifluoromethyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2008/13622; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

25016-11-9, name is 1-Methyl-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 C5H6N2O

EXAMPLE 51 (Z)-2-(5-methoxy-1H-indol-3-yl)-3-(1-methyl-1H-pyrazol-3-yl)-acrylonitrile To a solution of sodium methanolate (204 mg, 3.8 mmol, 1.4 eq.) in anhydrous ethanol (30 mL) were added, under an argon atmosphere, (5-methoxy-1H-indol-3-yl)-acetonitrile (500 mg, 2.7 mmol, 1.0 eq.) and, after 30 minutes stirring, 1-methyl-1H-pyrazole-4-carbaldehyde (326 mg, 3.0 mmol, 1.1 eq.). The reaction apparatus was protected from light and the mixture heated at 50 C. for 18 hours. The reaction was allowed to cool to room temperature and then, the solvent was removed under reduced pressure and the crude taken up in ethyl acetate. The organic layer was washed with water and brine, dried over MgSO4 and then, evaporated. The residue was purified by silica gel flash-column chromatography (eluent: CH2Cl2/EtOH, 99/1 to 98/2) to afford, after trituration with diethyl ether, the compound (51) as a beige powder (640 mg, 85%). mp: 178 C.; 1H NMR (DMSO, 300 MHz) delta (ppm): 3.81 (3H, s, 5′-methoxy), 3.92 (3H, s, N-methyl), 6.90 (1H, dd, J6′-7’=8.7 Hz, J6′-4’=2.3 Hz, H6′), 7.37 (1H, d, J7′-6’=8.7 Hz, H7′), 7.38 (1H, m, H4′), 7.55 (1H, s, H3), 7.61 (1H, s, H2′), 8.00 (1H, s, H3″), 8.24 (1H, s, H5″), 11.43 (1H, s, indolic H); 13C NMR (DMSO, 75.5 MHz) delta (ppm): 38.8 (N-methyl), 55.6 (5′-methoxy), 101.5 (C2), 101.5 (C4′), 109.8 (C3′), 111.9 (C6′), 112.9 (C7′), 117.4 (C4″), 119.3 (C1), 124.0 (C3a’), 125.6 (C2′), 128.5 (C3), 131.0 (C5″), 132.1 (C7a’), 138.8 (C3″), 154.1 (C5′); MS: ESI-MS: m/z 264.1 ([M+H]+), 286.1 ([M+Na]+); HRESI-MS: m/z 301.1060 (calcd for C16H14N4ONa+, 301.1065); Anal. Calcd for C19H14N4O, 0.1H2O: C, 68.61; H, 5.11; N, 20.00; O, 6.55. Found: C, 68.73; H, 5.33; N, 19.69.

The synthetic route of 25016-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COMMISSARIAT A L’ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; Guillou, Catherine; Kozielski, Frank; Labriere, Christophe; Gueritte, Francoise; Tcherniuk, Sergey; Skoufias, Dimitrios; Thal, Claude; Husson, Henri-Philippe; US9212138; (2015); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 5334-39-4, These common heterocyclic compound, 5334-39-4, name is 3-Methyl-4-nitro-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.

To a solution of 3 -methyl ~4-nitro- lH-pyrazole ( 10 g, 78,68 mmol) in DMF (50 mL) was added portionwise NaH (4.72 g, 1 18 ,02 mmol, 60% purity) at 0 C over 30 min. After addition, the mixture was stirred at 20 C for 30 min, and then 3- bromo-3-methylbutan-2-one ( 15.58 g, 94.42 mmol) was added dropwise at 0 C. The resulting mixture was stirred at 20 C for 1 1 h. The reaction mixture was quenched by addition of H20 (250 mL) at 0C, and extracted with EtOAc (3 chi 100 mL). The combined organic layers were washed with brine (50 mL), dried over Na2SO/j, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel (PE/EtOAc = 20/1 to 3/1). 3-methyl-3-(3-methyi-4- nitro-lH-pyrazol-l-yl)butan-2-one was obtained as a yellow solid. LCMS: RT 0.674 min, m/z = 212 [M + H]+. ‘H NMR (400 MHz, CDC13): 6 ppm 8.30 (s, 1 H) 2.56 (s, 3 H) 1.98 (s, 3 H) 1.75 (s, 6 H)

The synthetic route of 5334-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics