Category: 16034-46-1

Application of 16034-46-1,Some common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C5H6N2O2, 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.

DIPEA (1.05 mL, 6.35 mmol) was added to a stirred solution of Intermediate 1130 (500 mg, 2.12 mmol), 1-methyl-1H-pyrazole-5-carboxylic acid (269 mg, 2.12 mmol) andHATU (969 mg, 2.55 mmol) in anhydrous DMF (10 mL) under a nitrogen atmosphere.The mixture was stirred at 20C for 18 h, then quenched with saturated aqueous sodiumhydrogen carbonate solution (50 mL) and water (50 mL). The material was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine (2 x50 mL) and dried over sodium sulfate, then filtered and concentrated in vacuo. Theresidue was purified by flash column chromatography, using a gradient of ethyl acetate inheptane (0-100%), to afford the title compound (618 mg, 99%) as a yellow-orange oil. DH5 (500 MHz, DMSO-d6) 8.60 (d,J8.3 Hz, 1H), 7.46 (d,J2.1 Hz, 1H), 7.01 (d,J2.1 Hz,1H), 4.37 (t, J8.1 Hz, 1H), 4.01 (s, 3H), 3.66 (s, 3H), 2.22-2.08 (m, 1H), 1.80-1.38 (m,13H), 1.37-1.29 (m, 1H). HPLC-MS (method 5): MH+ m/z 308, RT 1.87 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-pyrazole-5-carboxylic acid, its application will become more common.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHAPPELL, Rose Elizabeth; DEBOVES, Herve Jean Claude; FOLEY, Anne Marie; FOULKES, Gregory; JONES, Elizabeth Pearl; LECOMTE, Fabien Claude; QUINCEY, Joanna Rachel; SCHULZE, Monika-Sarah Elisabeth Dorothea; SELBY, Matthew Duncan; SMALLEY, Adam Peter; TAYLOR, Richard David; TOWNSEND, Robert James; ZHU, Zhaoning; (278 pag.)WO2018/229079; (2018); 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. 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C5H6N2O2

To a solution of 4-bromoaniline (200 mg, 1.16 mmol, 1 eq) in EtOAc (5 mL) was added 2-methylpyrazole-3-carboxylic acid (175.95 mg, 1.40 mmol, 1.2 eq), DIEA (450.78 mg, 3.49 mmol, 607.52 muL, 3 eq) and T3P (2.22 g, 3.49 mmol, 2.07 mL, 3 eq). The mixture was stirred at 60 C. for 12 h. Sat. NaHCO3 solution (10 mL) was added and the mixture was extracted with ethyl acetate (10 mL*3). The combined organic layers were washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated to afford the crude product which was purified on silica gel column chromatography (from PE/EtOAc=1/0 to 3/1, TLC: PE/EtOAc=2/1, Rf=0.47) to give N-(4-bromophenyl)-2-methyl-pyrazole-3-carboxamide (198 mg, 699.77 mumol, 60.2% yield, 99.0% purity) as a white solid. 1H NMR (400 MHz, CDCl3) delta ppm 7.61 (s, 1H), 7.49 (d, J=2.0 Hz, 1H), 7.47 (s, 4H), 6.63 (d, J=2.0 Hz, 1H), 4.20 (s, 3H); ES-LCMS m/z 279.6 [M+H]+.

According to the analysis of related databases, 16034-46-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kyn Therapeutics; Castro, Alfredo C.; Evans, Catherine Anne; (108 pag.)US2019/55218; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, 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. Product Details of 16034-46-1

General procedure: The DCC (1.2 equiv) was added to the solution of 1 (0.2 mmol), DMAP (0.2 equiv), and appropriate carboxylic acid (1.2 equiv) in anhydrous CH2Cl2 (8 mL) at 0 C. The resulting mixture was stirred at room temperature until the starting material was not observed by TLC. The reaction mixture was filtered, and the residue was washed with CH2Cl2 (2 × 10 mL). Then, the CH2Cl2 solution was washed with 5% HCl (3 × 30 mL), saturated NaHCO3 (3 × 30 mL) and saturated NaCl (3 × 30 mL), respectively. Subsequently, the organic layer was dried over anhydrous Na2SO4 and concentrated to dryness under reduced pressure. At last, the residue was purified by column chromatography over the silica gel to yield the pure target compounds.

The synthetic route of 1-Methyl-1H-pyrazole-5-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Li-Jun; Geng, Chang-An; Ma, Yun-Bao; Huang, Xiao-Yan; Luo, Jie; Chen, Hao; Guo, Rui-Hua; Zhang, Xue-Mei; Chen, Ji-Jun; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 2877 – 2888;,
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. 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, A new synthetic method of this compound is introduced below., Computed Properties of C5H6N2O2

A mixture of 2-methyl-4-(6-(trifluoromethyl)quinolin-2-yl)aniline (10 g, 33.08 mmol, 1.00 equiv), l-methyl-lH-pyrazole-5-carboxylic acid (4.4 g, 34.89 mmol, 1.05 equiv), DIPEA (8.5 g, 65.77 mmol, 2.00 equiv) and HATU (4.4 g, 11.57 mmol, 1.50 equiv) in DMF (200 mL) was stirred overnight at room temperature. The reaction was quenched by the addition of 600 mL of water, extracted three times with 200 mL of ethyl acetate and the combined organic layers washed with 50 mL of water. Volatiles were eliminated under reduced pressure. The crude product was purified by recrystallization with methanol to afford the desired final product as a yellow solid in 76% yield. (ES, m/z): [M+H]+ 411; -NMR (DMSO-de, 300MHz, ppm): 52.40(s,3H), 54.12(s,3H), 57.12-7.13(d,lH), 57.57-7.61(m,2H), 58.00-8.04(d,lH), 58.19-8.36(m, 4H), 58.54 (s, 1H), 58.66-8.69 (d, 1H), 510.00 (s,lH).

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.

Related Products of 16034-46-1, The chemical industry reduces the impact on the environment during synthesis 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, I believe this compound will play a more active role in future production and life.

General procedure: The appropriate carboxylic acid (34.2 lmol, 2 eq), EDCIHCl(5.30 mg, 34.2 lmol, 2 eq) and DMAP (17.1 lmol, 1 eq) were combinedin CH2Cl2 (2 mL) and stirred at RT for 10 min. Amine 15(10.0 mg, 17.1 lmol, 1 eq) was added and the resulting mixturestirred at RT overnight. Reaction was, quenched by the additionof saturated aqueous NH4Cl solution (5 mL), extracted with EtOAc(3 5 mL) and the combined organic layers washed with 0.1 Maqueous KOH solution, brine, dried (MgSO4), filtered and concentratedin vacuo.

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-pyrazole-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Electric Literature of 16034-46-1, The chemical industry reduces the impact on the environment during synthesis 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, I believe this compound will play a more active role in future production and life.

To a solution of 2-methyl-4-(2-phenylethynyl)aniline (50 mg, 226.76 mumol, 1 eq) in pyridine (3 mL) was added T3P (288.60 mg, 453.51 mumol, 269.72 muL, 50%, 2 eq) and 2-methylpyrazole-3-carboxylic acid (28.60 mg, 226.76 mumol, 1 eq). The mixture was stirred at 20 C. for 16 h. The reaction mixture was quenched by addition water (50 mL), extracted with EtOAc (30 mL*3). The combined organic layers were washed with brine (10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue which was purified by preparative HPLC (column: Phenomenex Gemini 150*25 mm*10 um; mobile phase: [water(0.05% HCl)-ACN]; B %: 47%-77%, 10 min) followed by lyophilization to yield 2-methyl-N-[2-methyl-4-(2-phenylethynyl)phenyl]pyrazole-3-carboxamide (compound I-28, 32.57 mg, 92.57 mumol, 40.8% yield, 100% purity, HCl) as a light yellow solid. 1H NMR (400 MHz, CD3OD) delta ppm 7.56-7.49 (m, 3H), 7.47 (s, 1H), 7.42-7.35 (m, 5H), 6.98 (s, 1H), 4.15 (s, 3H), 2.31 (s, 3H); ES-LCMS m/z 316.0 [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-pyrazole-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Related Products of 16034-46-1, 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. 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 1 -methyl- lH-pyrazole-5-carboxylic acid (5 g, 39.7 mmol) in methanol (100 mL) was added thionyl chloride (103.2 mmol) under argon atmosphere at 0 C. The reaction mixture was stirred to room temperature over 12 h. The reaction mixture was cone, in vacuo, then diluted with water (100 mL), carefully quenched with sat’d aqueous NaHCC”3, and extracted with ethyl acetate (100 mL x 3). The combined organic phase was dried with anhydrous sodium sulphate, filtered and the filtrate was concentrated to give afford the title compound as a white solid which was used without further purification (5 g, 90 %) m/z 240.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-pyrazole-5-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference of 16034-46-1,Some common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C5H6N2O2, 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.

Oleum (1977mmol) is slowly added to fuming nitric acid (777 mmol) followed by the addition of 2-methyl-2H-pyrazole-3-carboxylic acid (277 mmol) in small portions maintaining the reaction temperature below 6O0C. Stirring at this temperature is then continued for a further 1 h. On completion, the reaction mixture is poured onto crushed ice and extracted with ethyl acetate (300 mL x 3). The combined organic phases are washed with water (250 mL x 2) and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure to afford 2-methyl-4-nitro-2H-pyrazole-3- carboxylic acid as a light yellow solid. Compound wt: 23.6g, 50%.[00251] 1H NMR (400 MHz, OMSO-d6) delta: 8.29 (lH,s); 3.95 (3H, s).

The synthetic route of 16034-46-1 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, 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 16034-46-1, Application In Synthesis of 1-Methyl-1H-pyrazole-5-carboxylic acid

To a solution of tert-butyl [2-(3,5-difluorobenzyl)-4-methyl-1,3-thiazol-5-yl]carbamate (300 mg, 0.881 mmol) obtained in Example 220-D) in ethanol (2 mL) was added dropwise concentrated hydrochloric acid (0.630 mL) at room temperature, and the mixture was stirred at 50C for 3.5 hr. The reaction mixture was cooled to 0C, neutralized with 8N aqueous sodium hydroxide solution, adjusted to pH 10-11 with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was dissolved in DMA (8 mL), and 1-methyl-1H-pyrazole-5-carboxylic acid (134 mg, 1.06 mmol), HATU (403 mg, 1.06 mmol) and DIEA (0.0728 mL, 0.441 mmol) were added at room temperature. The reaction mixture was stirred at 60C for 3.5 hr, cooled to room temperature, water and 0.1N hydrochloric acid were added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (3:2-3:7)] and basic silica gel column chromatography [eluent: hexane-ethyl acetate (3:2-3:7)], and crystallized from ethyl acetate-hexane to give the title compound (144 mg) as colorless crystals (yield 47%). MS (ESI+): [M+H]+ 349. 1H NMR (300 MHz, DMSO-d6) delta 2.31 (3H, s), 4.05 (3H, s), 4.26 (2H, s), 7.04-7.17 (4H, m), 7.54 (1H, d, J = 2.3 Hz), 10.53 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-pyrazole-5-carboxylic acid, and friends who are interested can also refer to it.

Electric Literature of 16034-46-1, 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. 16034-46-1 name is 1-Methyl-1H-pyrazole-5-carboxylic acid, 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.

To a solution of 1-methyl-1H-pyrazole-5-carboxylic acid (compound 4A, 81 mg, 0.640 mmol), DIEA (286 mg, 2.22 mmol) in CH2Cl2 (10 mL) was added EDCI (189 mg, 0.985 mmol), DMAP (90 mg, 0.739 mmol) at -5 C., then the mixture was stirred at -5 C. for 30 min, (E)-2-methyl-4-(2-methylstyryl)aniline (compound 4, 110 mg, 0.493 mmol) was added, the mixture was stirred at -5 C. for 30 min, warmed to 25 C. and stirred for 11 hrs. TLC (petroleum ether:ethyl acetate=1:1, Rf=0.60) showed starting material consumed completely. The mixture was concentrated in vacuum to give yellow oil. The oil was purified by silica gel column chromatography (petroleum ether:ethyl acetate=100:0 to 60:40) to give (E)-1-methyl-N-(2-methyl-4-(2-methylstyryl)phenyl)-1H-pyrazole-5-carboxamide (compound I-5, 65 mg, 39% yield) as white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 9.86 (s, 1H), 7.66 (d, J=7.4 Hz, 1H), 7.52-7.58 (m, 2H), 7.49 (d, J=8.2 Hz, 1H), 7.32-7.44 (m, 2H), 7.16-7.23 (m, 3H), 7.05?7.14 (m, 2H), 4.09 (s, 3H), 2.42 (s, 3H), 2.27 (s, 3H); ES-LCMS m/z 332.3 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-pyrazole-5-carboxylic acid, and friends who are interested can also refer to it.