Introduction of a new synthetic route about C5H6N2O2

The synthetic route of 1-Methyl-1H-pyrazole-3-carboxylic acid has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 25016-20-0, name is 1-Methyl-1H-pyrazole-3-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. Computed Properties of C5H6N2O2

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 HC1, filtered, the solid product washed with water, and dried under vacuum to provide pyrazole- 3-carboxylic acid as a white solid (64.4 g, 57%). Dimethyl sulfate (236 g, 177 ML, 1.87 mol) was added dropwise over 45 min to a stirred solution of pyrazole-3-carboxylic acid (200 g, 1.78 mol) in 20% aqueous sodium hydroxide (850 ML) at 40 C. The reaction mixture was heated at 80 C for 2 h, cooled to room temperature, filtered, the filtrate acidified to pH 1 with concentrated HC1, the precipitate filtered, washed with water, and dried under vacuum to yield 1-METHYLPYRAZOLE-5-CARBOXYLIC acid (85 g, 38%). The filtrate was concentrated in vacuo to 800 ML, extracted with chloroform (15X400 mL), the organic phase dried over anhydrous magnesium sulfate, concentrated in vacuo, and the residue recrystallized from isopropanol to yield 1-METHYLPYRAZOLE-3-CARBOXYLIC acid (74 g) as a white crystalline solid. A suspension of the acid (90 g, 0.71 mol) and DMF (1 drop) in thionyl chloride (250 ML) was stirred at reflux under nitrogen for 2 h. The solvent was evaporated from the reaction mixture, the residue azeotroped with toluene (3X200 mL), diluted into toluene (250 mL), added to a suspension of Pd-C (10 wt%, 9.3 g) in toluene (500 ML), and the mixture stirred at reflux for 8 h with a gentle flow of hydrogen gas through the suspension. After cooling to room temperature, the suspension was filtered through celite, washed with toluene, and concentrated in vacuo. The residue was fractionally distilled under vacuum to provide the title compound (50 g, 63%) as a low melting white solid (bp = 92 C @ 8 MMHG).

The synthetic route of 1-Methyl-1H-pyrazole-3-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2004/58763; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Continuously updated synthesis method about 3,5-Dimethyl-4-nitro-1H-pyrazole

Statistics shows that 3,5-Dimethyl-4-nitro-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 14531-55-6.

Application of 14531-55-6, These common heterocyclic compound, 14531-55-6, name is 3,5-Dimethyl-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.

General procedure: A solution of 1.85g (0.01mol) of 2,4,6-trichloro-1,3,5-triazine in the 50mL THF was stirred at room temperature for 1h. Then, 3,5-dimethylpyrazole (2.94g, 0.03mmol) were added into the solution in batches. 5mL of triethylamine was added dropwise whilst stirring at room temperature. After 1h, the mixture was heated at 80C for 1h. After cooling and filtering off, the filtrate evaporated on a steam bath and then washed with hot-water.

Statistics shows that 3,5-Dimethyl-4-nitro-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 14531-55-6.

Reference:
Article; Wang, Ji-Xiao; Zhu, Zi-Ran; Bai, Feng-Ying; Wang, Xin-Yu; Zhang, Xiao-Xi; Xing, Yong-Heng; Polyhedron; vol. 99; (2015); p. 59 – 70;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Research on new synthetic routes about 1-Methylpyrazole

According to the analysis of related databases, 930-36-9, the application of this compound in the production field has become more and more popular.

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. 930-36-9, name is 1-Methylpyrazole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H6N2

A solution of N-methylpyrazole (5.12 g, 62.4 mmol) in THF (100 mL) was cooled to -78 C. and 2.5 M n-butyllithium in hexane (27.5 mL, 68.8 mmol) was added. After stirring for 30 minutes at the same temperature, 0.5 M zinc chloride in THF (107 mL, 53.5 mmol) and 1 M zinc chloride in diethyl ether (15.3 mL, 15.2 mmol) were added. The mixture was allowed to warm to room temperature and 2-iodo-4-nitroanisole (17.4 g, 62.4 mmol) followed by tetrakis(triphenylphosphine)palladium (3.6 g, 3.1 mmol) were added. After stirring at 60 C. for 20 hours, the black solution was concentrated on a rotary evaporator, and extracted with ethyl acetate and brine. Combined organic layers were dried over magnesium sulfate, filtered, and partly concentrated until a solid started to precipitate. Hexane was added, precipitate was filtered off, and washed with a cold 3:1 mixture of hexane/ethyl acetate to give 5-(2-methoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole (8.6 g, 36.9 mmol, 59%) as a tan solid. LCMS m/z (%/o)=234 (M+H, 100). 1H NMR (400 MHz, CDCl3) delta: 8.34 (dd, J=2.8, 9.2 Hz, 1H), 8.19 (d, J=2.8 Hz, 1H), 7.56 ( d, J=2.0 Hz, 1H), 7.08 (d, J=9.2 Hz, 1H), 6.31 (d, J=1.6 Hz, 1H), 3.96 (s, 3H), 3.74 (s, 3H).

According to the analysis of related databases, 930-36-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Teegarden, Bradley; Xiong, Yifeng; Strah-Pleynet, Sonja; Jayakumar, Honnappa; Dosa, Peter I.; Feichtinger, Konrad; Casper, Martin; Lehmann, Juerg; Jones, Robert M.; Unett, David J.; Karoline Choi, Jin Sun; US2007/207994; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Continuously updated synthesis method about 5-Chloro-3-methyl-1H-pyrazole

The synthetic route of 15953-45-4 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 15953-45-4, A common heterocyclic compound, 15953-45-4, name is 5-Chloro-3-methyl-1H-pyrazole, molecular formula is C4H5ClN2, 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 solution ofKMnC>4 (3.5 g, 22 mmol) in water (120 mL) was added in portions over aperiod of 5 h at 70 C to a solution of5-chloro-3-methylpyrazole (1.0 g, 8.8 mmol; see step (c) above) in water (50 mL) and fc/^-butanol (1 mL). The mixture was stirred at 70 C overnight and filtered through Celite. The colourless filtrate was concentrated and acidified with HC1 (2M). Filtration gave the title compound as a white powder which was used without further purification. (Yield: 913 mg, 80%). ^-NMR (DMSO-dg): 5 13.65 (br s, 1H), 6.80 (s, 1H), 4.40 (bs, 1H).; A mixture of5-chloro-3-methylpyrazole (3.6 mmol; see step (a) above), water (6 mL), /e/Y-butanol (1.2 mL) and KMn04 (1.42 g, 9 mmol) was stirred at 75 C overnight. The hot mixture was filtered and the solids washed with boiling water. The combined filtrates were extracted twice with EtOAc. The combined extracts were washed with Nad (aq, sat), dried (MgS04) and concentrated to provide a solid, which was crystallised from EtOAc/hexane/pentane to give the sub-title product as white crystals (Yield: 350 mg (67%)). ‘H-NMR (DMSO-dg, 400 MHz), 5 13.65 (br s, 1H), 6.80 (s, 1H), 4.40 (bs, 1H).

The synthetic route of 15953-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOLIPOX AB; WO2006/32851; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Extracurricular laboratory: Synthetic route of 1150271-23-0

Statistics shows that tert-Butyl 4-bromo-1H-pyrazole-1-carboxylate is playing an increasingly important role. we look forward to future research findings about 1150271-23-0.

Synthetic Route of 1150271-23-0, These common heterocyclic compound, 1150271-23-0, name is tert-Butyl 4-bromo-1H-pyrazole-1-carboxylate, 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.

tert-Butyl 4-bromopyrazole-1-carboxylate (230 mg, 0.931 mmol), tert-butyl 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydropyrrole-1-carboxylate (250 mg, 0.847 mmol) and potassium carbonate (1.3 mL of 2M, 2.60 mmol) were combined in dioxane (3 mL) and the mixture de-gassed (x 2 vacuum cycles). Pd(dppf)Cl2.DCM (70 mg, 0.086 mmol) was added and the mixture de-gassed (x 2 vacuum cycles) then heated at 90 C overnight. The reaction mixture was partitioned between EtOAc and water. The organic phase was dried (Na2SO4), filtered and concentraed in vacuo. The residue was purified by chromatography (silica, 0-100% EtOAc/Petroleum ether gradient elution). Product fractions were combined and concentrated to give the product as a pale yellow film (65 mg, 33%) that was taken on to the next reaction. ESV- MS m/z 236.0 (M+1) +.

Statistics shows that tert-Butyl 4-bromo-1H-pyrazole-1-carboxylate is playing an increasingly important role. we look forward to future research findings about 1150271-23-0.

Reference:
Patent; MERCK PATENT GMBH; VERTEX PHARMACEUTICALS INCORPORATED; BLEICH, Matthew; CHARRIER, Jean-Damien; DONG, Huijun; DURRANT, Steven; ENO, Meredith Suzanne; ETXEBARRIA I JARDI, Gorka; EVERITT, Simon; FRAYSSE, Damien; KNEGTEL, Ronald; MOCHALKIN, Igor; NORTH, Kiri; PORICHIS, Filippos; PULLIN, Robert; QIU, Hui; STORCK, Pierre-Henri; TWIN, Heather Clare; XIAO, Yufang; (312 pag.)WO2019/148136; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

New downstream synthetic route of 175137-46-9

The synthetic route of 5-Cyclopropyl-1H-pyrazol-3-amine has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, 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. SDS of cas: 175137-46-9

5,6-Chloro-iV-(5-cvclopropyl-l//-pyrazol-3-yl)-3-nitropyridine-2-amine To a solution of 2,3,6-trichloro-5-nitropyridine (1.62 g, 7.10 mmol) and DIEA (1.24 ml, 7.1 mmol) in THF (25 ml) was added dropwise a solution of 5-cyclopropyl-lH”-pyrazol-3- amine (0.70 g, 5.68 mmol) in THF (5 ml) at 0 0C. After addition, the reaction mixture was stirred at 25 0C for 24 hours. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : EtOAc = 1.5 : 1) to give the title compound as a yellow solid (0.83 g, 47%). NMR (400 MHz) 12.39 (s, IH), 10.12 (s, IH), 8.77 (d, J= 1.2 Hz, IH), 6.35 (s, IH), 1.95 (m, IH), 0.96 (m, 2H), 0.71 (m, 2H). MS: Calcd.: 313; Found: [M+H]+ 314.

The synthetic route of 5-Cyclopropyl-1H-pyrazol-3-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/87530; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Share a compound : 37687-24-4

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl 3,5-pyrazoledicarboxylate, and friends who are interested can also refer to it.

Electric Literature of 37687-24-4, 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. 37687-24-4 name is Diethyl 3,5-pyrazoledicarboxylate, 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.

Diethyl 3,5-pyrazoledicarboxylate (2.12 g, 10.0 mmol, 1.00 eq) and N-Boc-ethanolamine (3.22 g, 20.0 mmol, 2.00 eq.) were dissolved in THF (72.0 mL) and triphenyl phosphine (4.72 g, 18.0 mmol, 1.80 eq.) was added. After 5 min, the mixture was cooled to 0 C. and di-tert-butyl azodicarboxylate (4.11 g, 18.0 mmol, 1.80 eq.) was added. The reaction mixture was then subjected to microwave irradiation for 20 min at 120 C. The mixture was cooled to room temperature and the solvent was removed in vacuo. Purification via flash chromatography on silica gel provided the title compound as a white powder (3.25 g, 91.5% yield). ES-MS [M+1]+: 300.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl 3,5-pyrazoledicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Vanderbilt University; Conn, P. Jeffrey; Lindsley, Craig W.; Emmitte, Kyle A.; Engers, Julie L.; Konkol, Leah C.; US2015/361081; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

The important role of 5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile, its application will become more common.

Application of 51516-70-2,Some common heterocyclic compound, 51516-70-2, name is 5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile, molecular formula is C10H7FN4, 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 stirred solution of the intermediate compounds 1a-1d (1 mmol) and triethylamine (2 mmol) in DMF (12 mL) medium, a mixture of EDCI (1 mmol) and HOBt (1mmol) was added and the reaction mixture was stirred at room temperature for 30 min, then a mixture of compounds 2a-2d (1 mmol) and DMF (5 mL) was added, the reaction was stirred at room temperature. And the reaction progress was monitored by TLC. After completion of the reaction, the product was added into chloroform, then extracted from chloroform with water, and washed successively with 0.2 mol/L hydrochloric acid, water,2 mol/L sodium hydroxide, water, saturated sodium chloride, then dried, concentrated and purified by preparative thin layer chromatography (PE:EA = 8:1) followed by recrystallization from ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile, its application will become more common.

Reference:
Article; Xiao, Jin-Jing; Liao, Min; Chu, Ming-Jie; Ren, Zi-Li; Zhang, Xin; Lv, Xian-Hai; Cao, Hai-Qun; Molecules; vol. 20; 1; (2015); p. 807 – 821;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

New downstream synthetic route of Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate

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.

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. 866837-96-9, name is Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Formula: C12H13N3O2

A solution of 5-(6-((tert-butoxycarbonyl)amino)pyridin-2-yl)-2,4-dichlorobenzoic acid (Preparation 24, 620 mg, 1.62 mmol), ethyl 5-amino-1-phenyl-1 H-pyrazole-3- carboxylate (374 mg, 1.62 mmol) and DIPEA (0.847 mL, 4.86 mmol) in 2- methyltetrahydrofuran (15 mL) was heated under nitrogen to 85C. To the solution was added T3P (50% in EtOAc; 2.90 mL, 4.86 mmol) dropwise over 5 minutes. The reaction was heated at 85C for 5 hours before cooling to room temperature and partitioning between saturated aqueous NaHCC solution (30 mL) and EtOAc (20 mL). The aqueous layer was washed with EtOAc (20 mL), the organic layers combined, dried over sodium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 30-50% TBME in heptanes to afford the title compound as a white solid (750 mg, 77%). 1 H NMR (400MHz, CDCI3): delta ppm 1 .41 (t, 3H), 1.56 (s, 9H), 4.45 (m, 2H), 7.01 (s, 1 H), 7.30 (d, 1 H), 7.40 (s, 1 H), 7.50-7.62 (m, 5H), 7.73 (t, 1 H), 7.97 (d, 1 H), 8.14 (s, 1 H), 8.42 (s, 1 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.; BAGAL, Sharanjeet Kaur; CUI, Jingrong Jean; GREASLEY, Samantha Elizabeth; LUNNEY, Elizabeth Ann; MCALPINE, Indrawan James; NAGATA, Asako; NINKOVIC, Sacha; OMOTO, Kiyoyuki; SKERRATT, Sarah Elizabeth; STORER, Robert Ian; WARMUS, Joseph Scott; WO2015/159175; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

The important role of 152120-54-2

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, tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, other downstream synthetic routes, hurry up and to see.

Adding a certain compound to certain chemical reactions, such as: 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, 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 152120-54-2, Recommanded Product: tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate

To a mixture of N,N’-bis(tertbutoxycarbonyl)-1H-pyrazole-1-carboxamidine (2g, 6.44 mmol), triphenylphosphine (2.53g, 9.67 mmol), MeOH (260 muL, 6.44 mmol) and dry THF (20 mL) was added dropwise DIAD ( 1.9 mL, 9.67 mmol) at 0C under argon. The reaction mixture was stirred at room temperature overnight. Then a solid was filtered off and the filtratrate was concentrated under reduced pressure. A residue was washed with hexane (6 x 50mL). Hexane was evaporated and the residue was purified by column chromatography on silica gel (hexane/AcOEt, 7: 1 to 5: 1) to give tert-butyl (((tert-butoxycarbonyl)imino)(1H-pyrazol-1-yl)methyl)(methyl)carbamate (1.49 g, 71 %) as a colorless oil . ESI+MS: m/z = 347.1 (M+1)+. 1Eta NMR (700 MHz, Chloroform-d) delta 8.02 (s, 1H), 7.71 (d, J= 1.1 Hz, 1H), 6.45 (ddd, J = 8.7, 2.7, 1.6 Hz, 1H), 3.27 (s, 3H), 1.54 (s, 9H), 1.32 (s, 9H).

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, tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ONCOARENDI THERAPEUTICS SP. Z O.O.; B?ASZCZYK, Roman; BRZEZI?SKA, Joanna; GO??BIOWSKI, Adam A.; OLCZAK, Jacek; (93 pag.)WO2016/108707; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics