Day: July 20, 2021

Adding a certain compound to certain chemical reactions, such as: 2075-45-8, name is 4-Bromo-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 2075-45-8, category: pyrazoles-derivatives

A 100 mL round bottom flask was charged with 4-bromopyrazole (4.41 g, 30 mmol), tetrabutylammonium bromide [(484] mg, 1.5 mmol) and potassium hydroxide pellets (3.37 g, 60 mmol). After the mixture was sonicated for 15 min, benzyl chloride (5.2 [ML,] 45 mmol) was added dropwise and the resulting mixture was stirred overnight. Ethyl ether (20 mL), water (20 mL), and diluted hydrochloric acid (1 [ML,] [10%)] were added under stirring. The organic layer was washed with water [(2X20] mL) and dried over MgS04. The solvent was removed under reduced pressure and the product was purified by flash chromatography on silica gel (hexane/ethyl acetate 10: 1) to provide the desired product as a white solid (6.74 g, 95% yield). Mp [51-52 C] (lit. [44-45 C,] See Jones, R. G. [J.] Am. [CHEM.] Soc. 1949, [71,] [3994).’H NMR] (400 MHz, CDC13) : [8] 7.53 (s, 1H), 7.42-7. 33 (m, 4H), 7.28-7. 22 (m, 2H), 5.29 (s, 2H); [13C] NMR (100 MHz, CDC13) : [6] 140.4, 136.2, 129. 8, 129.4, 128.8, [128.] 3,93. 9, 57.1.

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, 4-Bromo-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; WO2004/13094; (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. 72760-85-1, name is 3-Amino-5-(methylthio)-1H-pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., Quality Control of 3-Amino-5-(methylthio)-1H-pyrazole-4-carbonitrile

General procedure: An equimolar mixture of Int-I (chalcones) and Int-II (5-amino-3-(methylthio)-1H-pyrazole-4-carbonitrile) was refluxed in n-butanol for 4-5 h. The completion of reaction was confirmed by Thin Layer Chromatography using (6:4- hexane: ethyl acetate) as a mobile phase. The reaction mixture was then allowed to cool and the resulting solid was filtered and washed with diethyl ether to remove impurities. The procedure was repeated 3-4 times to free the product from impurities.

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; Baluja, Shipra; Nandha, Kajal; Journal of Molecular Liquids; vol. 201; (2015); p. 90 – 95;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 42098-25-9, 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. 42098-25-9 name is 5-Chloro-1-methyl-4-nitro-1H-pyrazole, 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.

Example 78 tert-Butyl (1-(4-amino-1-methyl-1H-pyrazol-5-yl)piperidin-4-yl)methylcarbamate A solution of 5-chloro-1-methyl-4-nitro-1H-pyrazole from Example 1 (1.9 g, 11.77 mmol), 4-(boc-aminomethyl)piperidine (3.78 g, 17.66 mmol) and DIPEA (6.15 mL, 35.31 mmol) in EtOH (20 mL) was heated in a microwave at 130 C. for 1 hr. The solvent was removed under reduced pressure and the residue re-dissolved in DCM. The organic layer was washed with water, passed through a phase separation cartridge and concentrated under reduced pressure. The residue was purified via silica gel column chromatography (0-100% EtOAc/isohexane) to yield tert-butyl (1-(1-methyl-4-nitro-1H-pyrazol-5-yl)piperidin-4-yl)methylcarbamate as a yellow solid (3.95 g, 98%). To a solution of this solid (3.84 g, 11.30 mmol) in MeOH (125 mL) was added 10% Pd/C (0.42 g, 3.96 mmol) and ammonium formate (2.85 g, 45.2 mmol). The mixture was heated at 80 C. for 2.5 hr. The mixture was concentrated under reduced pressure and the residue was re-dissolved in EtOAc and washed with water. The organic layer was passed through a phase separation cartridge and concentrated under reduced pressure to give tert-butyl (1-(4-amino-1-methyl-1H-pyrazol-5-yl)piperidin-4-yl)methylcarbamate as a brown oil (3.49 g, 99%). 1H NMR (400 MHz, CDCl3) delta 7.04 (s, 1H), 4.63 (s, 1H), 3.64 (s, 3H), 3.11-3.07 (m, 6H), 2.67 (s, 2H), 1.77 (d, J=12.8 Hz, 2H), 1.45 (s, 9H), 1.39-1.26 (m, 2H). 1H hidden by water peak.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-1-methyl-4-nitro-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; Hodges, Alastair James; Matteucci, Mizio; Sharpe, Andrew; Sun, Minghua; Wang, Xiaojing; Tsui, Vickie H.; US2013/79321; (2013); 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. 288-13-1, name is 1H-Pyrazole, A new synthetic method of this compound is introduced below., COA of Formula: C3H4N2

At room temperature, pyrazole (0.2 mol) was dissolved in concentrated sulfuric acid (50 mL) and slowly raised to a temperature of 60 CConcentrated nitric acid (9.2 mL) was added and stirring was continued at 60 C for 1.5 hours.After completion of the reaction, the reaction solution was poured into 600 g of ice water, and the resulting white solid was separated by filtration and washed with water.After extraction with ethyl acetate (100 mL x 3), the organic phase was washed successively with 1% sodium bicarbonate solution (100 mL), water (100 mL) and physiological saline (100 mL), dried over anhydrous sodium sulfate and filtered, Finally, the organic phase liquid was rotary evaporated to give a white solid which was combined with the previously obtained white solid to give compound 2a. The resulting compound 2a (12 mmol) was dissolved in DMSO (9 mL)And potassium carbonate (10.9 mmol) was added successively thereto,Methyl iodide (6 mmol),8-hydroxyquinoline (1 mmol),CuI (0.58 mmol). Argon under the conditions of protection, stirMixed and heated to 130 C,After 20 hours of reaction,The reaction solution was poured into an appropriate amount of water,The resulting green solid was separated by filtration.The mother liquor was extracted with ethyl acetate (100 mL x 3). Finally, the organic phase liquid was evaporated to dryness and the resulting crude product was combined with the previously obtained green solid and purified by silica gel column chromatography to obtain Compound 4a. Compound 4a (1 mmol), hydrazine hydrate (0.5 mL) was added to ethanol (1 mL) and palladium on carbon (0.02 g) was added as catalyst.Heated at 80 C and refluxed for 10 minutes. After the completion of the reaction, the resulting mother liquor was subjected to rotary evaporation and drying to obtain Compound 5a. Compound 4a (1 mmol), hydrazine hydrate (0.5 mL) was added to ethanol (1 mL) and palladium on carbon (0.02 g) was added as catalyst.Heated at 80 C and refluxed for 10 minutes. After the completion of the reaction, the resulting mother liquor was subjected to rotary evaporation and drying to obtain Compound 5a. The compound 8a (1 mmol),EDC (1 mmol), HOBt (1 mmol) was added to DMF(3 mL) for 30 min.The compound 5a, DMAP (1 mmol), triethylamine (500 [mu] L) were added to the activated DMFSolution. At room temperature, stir overnight.After completion of the reaction, 100 mL of saturated sodium chloride solution was added to the reaction solution, and the mixture was washed with ethyl acetateEster extraction (200 mL x 3) extraction. Finally, the organic phase liquid was evaporated under vacuum and evaporated to dryness to obtain a crude product, using a silica gel columnSeparation and purification to give the final compound 9a to give a white solid powder in a yield of 86.4%

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; Nanjing University; Zhu Hailiang; Shi Lu; Wang Zefeng; Wang Chenru; (14 pag.)CN107098861; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 20154-03-4, A common heterocyclic compound, 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, molecular formula is C4H3F3N2, 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.

Reference Example 15 Preparation of 2-Chloro-4-(3-trifluoromethylpyrazolyl)benzaldehyde (Compound XVI) 4.08 g (30.0 mmol) of 3-trifluoromethylpyrazol, 4.75 mmol (30.0 mmol) of 2-chloro-4-fluorobenzaldehyde and 4.14 g (30.0 mmol) of potassium carbonate in 30 ml of N,N-dimethylformamide were stirred at 60° C. for 2 hours. After cooling to room temperature, the reaction mixture was poured into 100 ml of water, and the organic matters were extracted with 50 ml of ethyl acetate twice. The ethyl acetate layers were combined, washed with 50 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. The residue afforded 7.18 g of 2-chloro-4-(3-trifluoromethylpyrazolyl)benzaldehyde (yield 87.2percent) as a pale yellow powder, after washed with n-hexane.

The synthetic route of 20154-03-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US6509354; (2003); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 400755-44-4, name is 1-Ethylpyrazole-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. Safety of 1-Ethylpyrazole-3-carboxylic Acid

A mixture of 5-(3,5-difluorobenzyl)pyridin-2-amine (0.100 g, 0.45 mmol), 1 -ethyl- 7/-/-pyrazole-3-carboxylic acid (0.053 g, 0.38 mmol), 1 -[b/s(dimethylamino)methylene]- 7/-/-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (0.1 73 g, 0.45 mmol) and A/,A/-diisopropylethylamine (0.147 g, 1 .14 mmol) in anhydrous A/,A/-dimethylformamide (4.00 mL) was stirred at 20 C for 2 h. The reaction solution was extracted with ethyl acetate (20 ml_ x 20). The combined organic layers were washed with water (50 mL) and brine (50 mL) were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude sample was dissolved in minimal A/,A/-dimethylformamide and purified via prep-HPLC (Boston C1 8 21 *250 mm 10 pm column; acetonitrile/0.01 % aqueous trifluoroacetic acid) to give A/-(5-(3,5-difluorobenzyl)pyridin-2-yl)-1 -ethyl- 7/-/-pyrazole-3-carboxamide (0.0304 g, 0.09 mmol, 23%) as a white solid. 1 H NMR (400 MHz, Dimethylsulfoxide-c/6) d 9.68 (s, 1 H), 8.32 (d, J = 1 .8 Hz, 1 H), 8.10 (d, J = 8.5 Hz, 1 H), 7.94 (s, 1 H), 7.79 (dd, J = 8.5, 2.2 Hz, 1 H), 7.13 – 6.95 (m, 3H), 6.85 (d, J = 2.3 Hz, 1 H), 4.26 (q, J = 7.3 Hz, 2H), 3.98 (s, 2H), 1 .44 (t, J = 7.3 Hz, 3H); LCMS (ESI) m/z: 343.1 [M+H]+.

The synthetic route of 1-Ethylpyrazole-3-carboxylic Acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUMANITY THERAPEUTICS, INC.; LE BOURDONNEC, Bertrand; LUCAS, Matthew; OZBOYA, Kerem; PANDYA, Bhaumik; TARDIFF, Daniel; TIVITMAHAISOON, Parcharee; WRONA, Iwona; (475 pag.)WO2019/183587; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 127107-23-7,Some common heterocyclic compound, 127107-23-7, name is 1-Methyl-1H-pyrazol-4-amine hydrochloride, molecular formula is C4H8ClN3, 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 8a (0.25 g, 0.95 mmol) and 1-methyl-1H-pyrazol-4-amine hydrochloridesalt (0.14 g, 1.1 mmol) in n-butanol (5 mL) was added trifluoroaceticacid (0.27 g, 2.4 mmol), and the mixture was stirredovernight at 120 C. The mixture was then concentrated, neutralizedwith ammonia in methanol, and purified by column chromatography(dichloromethane: methanol=60:1) to yield 0.26 g (86.7%) of 9a as apale-yellow solid. MS (ESI) m/z 326 [M+H]+.

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-pyrazol-4-amine hydrochloride, its application will become more common.

Reference:
Article; Yu, Ru-Nan; Chen, Cheng-Juan; Shu, Lei; Yin, Yuan; Wang, Zhi-Jian; Zhang, Tian-Tai; Zhang, Da-Yong; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1646 – 1657;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 112029-98-8, name is (1-Methyl-1H-pyrazol-4-yl)methanol, 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. Recommanded Product: 112029-98-8

To a cooled solution of (1-methyl-1H-pyrazol-4-yl)-methanol (8.61 g, 0.076 mole) in DCM (100 mL) under N2 atmosphere, thionyl chloride (8.7 mL, 0.12 mole) was added drop wise. The reaction mixture was warmed to RT and stirred for 2 hours. The reaction mixture was concentrated under vacuum at 23 ? 25 °C to obtain the titlecompound.Yield: 12.77 g (99 percent); ?H – NMR (DMSO-d6, 400 MHz) oe ppm: 3.85 (s, 3H), 4.67 (s, 2H), 4.76 – 4.79 (t, 1H), 4.88 (bs, 1H), 7.47 (s, 1H), 7.78 (s, 1H).

The synthetic route of (1-Methyl-1H-pyrazol-4-yl)methanol has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; NIROGI, Ramakrishna; SHINDE, Anil Karbhari; MOHAMMED, Abdul Rasheed; SUBRAMANIAN, Ramkumar; BENADE, Vijay Sidram; BHYRAPUNENI, Gopinadh; JASTI, Venkateswarlu; (89 pag.)WO2017/42643; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, 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 5932-27-4, Product Details of 5932-27-4

To a solution of K2CO3 (94 mg, 0.66mmol) in DMF (8 mL) was added ethyl 1H-pyrazole-3-carboxylate (158 mg, 1.12 mmol). The mixture was stirred at 20 oC for 0.5 h under N2. Then to mixture was added a solution of A33 (100 mg, 0.22 mmol) in DMF (4 mL), and stirred at 20oC for 3 h. The mixture was diluted with EtOAc (50 mL), washed with brine (50mL*3) and the organic layer was dried over anhydrous Na2SO4, and then concentrated to give crude product. It was purification by column chromatography (petroleum ether: ethyl acetate = 4:1) to give the 40 (45 mg) as a yellow solid. 1H NMR (40): (400 MHz, CDCl3) delta 7.44 (d, J = 2 Hz, 1H), 6.87 (d, J = 2.4 Hz, 1H), 5.30 (s, 3H), 4.40 (dd, J =7.6 Hz, J =14.8 Hz, 2H), 3.96-3.91 (m, 1H), 3.60-3.53 (m, 1H), 3.47-3.38 (m , 2H), 2.60-2.52 (m, 1H), 2.21-2.11 (m, 1H), 2.07-2.00 (m, 1H), 1.90 -1.61 (m, 6H), 1.52-1.15 (m, 17H), 1.03 -0.92 (m, 4H), 0.82-0.72 (m, 1H), 0.66 (s, 3H)

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, Ethyl 1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

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

Application of 3398-16-1, A common heterocyclic compound, 3398-16-1, name is 4-Bromo-3,5-dimethylpyrazole, molecular formula is C5H7BrN2, 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.

4.2.6 3,3′,5,5′-Tetrakis[(4-brom-3,5-dimethyl-1H-pyrazol-1-yl)methyl]-2,2′,4,4′,6,6′-hexamethyldiphenylmethane (35) To a suspension of NaOH (192 mg, 4.81 mmol) in DMF (20 mL), 4-bromo-3,5-dimethyl-1H-pyrazole (841 mg, 4.81 mmol) (37) was added and stirred at room temperature for 20 min. After the addition of compound 20 (500 mg, 0.80 mmol) the reaction mixture was stirred for 72 h at room temperature. Afterwards, the mixture was poured into ice water (200 mL), the formed precipitate filtered off, washed thoroughly with distilled water and dried to constant mass in the desiccator. The desired compound 35 was obtained as a snow-white solid (750 mg, 94percent), mp 216 °C. 1H NMR (500 MHz, CDCl3): delta 5.17 (s, 8H), 4.18 (s, 2H), 2.19 (s, 6H), 2.12 (s, 12H), 2.05 (s, 12H), 2.01 (s, 12H) ppm. 13C NMR (CDCl3, 125 MHz): delta 145.52, 137.86, 137.12, 136.80, 135.81, 130.51, 94.17, 49.69, 33.36, 17.35, 16.53, 12.40, 10.35 ppm. MS (ESI): m/z 1000.8, 827.2, 681.0, 507.0, 333.0. Anal. Calcd for C43H52Br4N8: C, 51.62; H, 5.24; N, 11.20. Found: C, 51.39; H, 5.49; N, 11.38.

The synthetic route of 3398-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Koch, Niklas; Rosien, Jan-Ruven; Mazik, Monika; Tetrahedron; vol. 70; 45; (2014); p. 8758 – 8767;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics