Day: August 27, 2021

Adding a certain compound to certain chemical reactions, such as: 288-13-1, name is 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 288-13-1, Quality Control of 1H-Pyrazole

General procedure: A mixture of the appropriate N-nucleophile (2 mmol), 4-bromonitrobenzene(2 mmol), t-ButOK or KOH (in the case of 1g, 1h)(2.2 mmol) in dimethyl sulfoxide (2.5 mL) was stirred at 60 C for 5 h(8 h in the case of 1b). After cooling and addition of water (60 mL),either a solid precipitated which was filtered, washed with water andrecrystallised from an appropriate solvent to give the product, or asuspension was generated which was extracted with ethyl acetate(3 × 30 mL), dried over Na2SO4, concentrated under reduced pressureand recrystallised from an appropriate solvent to give the desiredproduct

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:
Article; Ghasemi, Zarrin; Shahrak, Nasim Shahi; Roomi, Behzad Jalali; Zakeri, Ziba; Journal of Chemical Research; vol. 39; 2; (2015); p. 73 – 75;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 63680-90-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 63680-90-0 as follows.

Step 2: Preparation of tert-butyl (3-chloro-1H-pyrazol-4-yl)carbamate Into a 2 L round bottom flask was added 3-chloro-1H-pyrazol-4-amine hydrochloride (100 g, 649 mmol) and THF (500 mL). To this mixture were added di-tert-butyldicarbonate (156 g, 714 mmol) followed by sodium bicarbonate (120 g, 1429 mmol) and water (50.0 ml). The mixture was stirred for 16 h, diluted with water (500 mL) and ethyl acetate (500 mL) and transferred to a separatory funnel. This gave three layers; bottom-a white gelatinous precipitate, middle-light yellow aqueous, top-auburn organic. The phases were separated collecting the white gelatinous precipitate and the aqueous layer together. The aqueous was extracted with ethyl acetate (2*200 mL) and the ethyl acetate extracts were combined, washed with brine (200 mL), dried over anhydrous sodium sulfate, filtered and rotary evaporated to give an auburn thick oil (160 g.). The thick oil was suspended in hexane (1000 mL) and stirred at 55 C. for 2 h. This gave a light brown suspension. The mixture was cooled to 0 C. and the solid collected by vacuum filtration and rinsed with hexane (2*10 mL). The sample was air dried to constant mass to afford (3-chloro-1H-pyrazol-4-yl)carbamate (102.97 g, 72% yield, 80% purity) as a light brown solid: mp 137-138 C.; 1H NMR (400 MHz, CDCl3) delta 10.69 (s, 1H), 7.91 (s, 1H), 1.52 (s, 9H).

According to the analysis of related databases, 63680-90-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOW AGROSCIENCES LLC; Buysse, Ann M.; Niyaz, Noormohamed M.; Demeter, David A.; Zhang, Yu; Walsh, Martin J.; Kubota, Asako; Hunter, Ricky; Trullinger, Tony K.; Lowe, Christian T.; Knueppel, Daniel; Patny, Akshay; Garizi, Negar; LePlae, JR., Paul Renee; Wessels, Frank; Ross, JR., Ronald; DeAmicis, Carl; Borromeo, Peter; US2013/288893; (2013); 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. 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Ethyl 1H-pyrazole-3-carboxylate

To a solution of ethyl 1 H-pyrazole-3-carboxylate (2 g) in MeCN (40 ml) was added cesium carbonate (4.65 g) and the mixture stirred for 30 min when 4-(bromomethyl)tetrahydro-2H- pyran (2.81 g) was added and the mixture stirred at RT for 18 h. The solvent was removed in vacuo and the residue partitioned between dichloromethane (50 ml) and water (20 ml), separated by hydrophobic frit and concentrated. The filtrate was purified by silica (2 x 100 g) cartridge on Flashmaster II using a gradient of DCM and ethyl acetate to give the title compound 1 as a colourless oil, 0.944 g and title compound 2, as a colourless oil, 1 .026g.1 ; LCMS (method B); Rt = 0.90 min, MH+ = 239.2; LCMS (method B); Rt = 0.75 min, MH+ = 239.

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 5932-27-4.

Reference:
Patent; GLAXO GROUP LIMITED; BALDWIN, Ian Robert; DOWN, Kenneth David; FAULDER, Paul; GAINES, Simon; HAMBLIN, Julie Nicole; JONES, Katherine Louise; JONES, Paul Spencer; LE, Joelle; LUNNISS, Christopher James; PARR, Nigel James; RITCHIE, Timothy John; ROBINSON, John Edward; SIMPSON, Juliet Kay; SMETHURST, Christian Alan Paul; WO2011/67365; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 83-10-3, These common heterocyclic compound, 83-10-3, name is 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-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.

Step 2) N-(5-hydroxypyridin-2-yl)-2.5-dimethyl-3-oxo-l-phenyl-2.3-dihydro-lH- pyrazole-4-carboxamide [0213] A suspension of 2-amino-5-hydroxypyridine hydrochloride (500 mg, 3.41 mmol) and Et3N (0.77 mL, 5.5 mmol) in DMF (8 mL) was stirred at rt for 1 hour. At the same time, to a solution of l,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-lH-pyrazole-4- carboxylic acid (0.64 g, 2.75 mmol), EtaOmicronAlphaTau (449 mg, 3.3 mmol) and EDCI (0.63 g, 3.3 mmol) in DMF (8 mL) was added Et3 (0.77 mL, 5.5 mmol) drop wise. The mixture was stirred at rt for 1 hour, followed by the addition of the above prepared mixture. The reaction was heated at 60 C for 5 hours, then cooled to rt and diluted with water (150 mL). and adjust to pH = 6 with HC1 (1 M). The mixture was extracted with EtOAc (20 mL x 4), and the combined organic phases were washed with brine (20 mL), dried over anhydrous a2S04, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/MeOH (v/v) = 10/1) to give the title compound as a pale yellow solid (699 mg, 78%). MS (ESI, pos. ion) m/z: 325.1 [M+H]+.

Statistics shows that 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 83-10-3.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; WU, Yanjun; LIAO, Min; FENG, Yanming; WO2014/22116; (2014); A2;,
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. 2033-45-6, name is 3,5-Dimethyl-4-iodopyrazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3,5-Dimethyl-4-iodopyrazole

To a solution of 3,5-Dimethyl-4-iodo-1 H-pyrazole (1 .69g, 7.61 mmol) in DCM (25ml_) was added 3,4- Dihydro-2H-pyran (1 .04mL, 1 1 .4mmol) and pyridinium p-toluenesulfonate (383mg, 1 .52mmol). The reaction was stirred at 40C overnight and then for for 4 days at room temperature. The mixture was diluted with DCM (50ml), washed with sat NaHC03 aq (50ml), dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (40g Si02, 0-30% EtOAc in heptane) to provide 4-iodo-3,5-dimethyl-1 -tetrahydropyran-2-yl-pyrazole (2.36g,7.7mmol, 101 .19% yield) as a white solid. MS Method 2: RT: 1 .78 min, ES+ m/z 307.0 [M+H]+ H NMR (400MHz, CDCI3) delta/ppm: 5.23-5.26 (d, J=10.4Hz, 1 H), 4.05-4.08 (m, 1 H), 3.62-3.69 (m, 1 H), 2.39-2.49 (m, 1 H), 2.35 (s, 3H), 2.25 (s, 3H), 2.09-2.14 (m, 1 H). 1 .88-1 .94 (m, 1 H), 1 .64-1 .79 (m, 3H).

According to the analysis of related databases, 2033-45-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; REDX PHARMA PLC; BHAMRA, Inder; BINGHAM, Matilda; TESTAR, Richard; SARGENT, Louise; DONOGHUE, Craig; (128 pag.)WO2016/55786; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1904-31-0,Some common heterocyclic compound, 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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.

97 Preparation of N.N-dicyclopropyl-6-ethyl- 1 -methyl -4-( 1 -methyl- 1H- pyrazol-3-ylamino)-1.6-dihydroimidazo[4.5-dlpyrrolo[2.3-blpyridine-7-carboxamide[00465] To a vial containing 1 -methyl- lH-pyrazol-3 -amine (11.89 mg, 0.122 mmol), Pd2(dba)3 (4.67 mg, 5.10 muiotaetaomicron), Xantphos (5.90 mg, 10.20 muiotaetaomicron), and cesium carbonate (100 mg, 0.306 mmol) was added 4-bromo-N,N-dicyclopropyl-6-ethyl-l- methyl-l,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 97A, 41.0 mg, 0.102 mmol) in DME (1020 muKappa). The reaction mixture was sparged with argon for 5 min, the vial was capped, and the reaction mixture was heated at 60 °C for 4 h and 80 °C for 16h. The reaction mixture was concentrated in vacuo. The crude residue was purified by flash column chromatography using an Isco 40 g column eluting with 0 – 5percent MeOH/ (3/4(3/4 followed by additional purification with preparative HPLC. N,N-Dicyclopropyl-6-ethyl-l-methyl-4-(l -methyl- lH-pyrazol-3 – ylamino)-l,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (13 mg, 0.030 mmol, 29.5percent yield) was isolated as a white solid.[00466] MS (ESI) m/z 419.3 (M+H) [00467] 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.17 (s, 1 H), 7.64 (s, 1 H), 7.31 (d, 1H, J= 2.26 Hz), 7.16 (d, 1 H, J= 2.26 Hz), 6.86 (s, 1 H), 4.65 (q, 2 H, J = 7.03 Hz), 4.01 (s, 3 H), 3.85 (s, 3H), 2.78 – 2.87 (m, 2 H), 1.49 (t, 3 H, J= 7.15 Hz), 0.81 – 0.89 (m, 4 H), 0.71 – 0.80 (m, 4 H)

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PURANDARE, Ashok V.; GREBINSKI, James W.; HART, Amy; INGHRIM, Jennifer; SCHROEDER, Gretchen; WAN, Honghe; WO2011/28864; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 28466-26-4, A common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, molecular formula is C3H5N3, 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.

Neat 1 H-pyrazol-4-amine (49.0 mg, 0.59 mmol) was added in one charge to a stirred solution of 2-[(phenylmethyl)oxy]-5-(4-pyndinyl)benzoic acid (may be prepared as described in Description 79; 150 mg, 0.49 mmol), EDC (283 mg, 1.47 mmol) and HOBT (226 mg, 1.47 mmol) in dimethylformamide (4 ml) in air at room temperature. The reaction mixture was stirred at room temperature overnight. 30 ml water was added, and the mixture was extracted with ethyl acetate (70 ml x 2). The organic layers were combined, dried over MgS04l and concentrated in vacuo. The residue was further purified by pre-HPLC (Gilson GX-281 ; Shimadzu 15mueta? 250*20mm; A: l OmMolNH4HC03/Water; B: CH3CN) to yield the title compound as a white solid. 50 mg.1HNMR (400 MHz, DMSO-cfe): 5.34 (s, 2H), 7.34-7.44 (m, 4H), 7.55 (d, 2H), 7.74 (d, 4H), 7.95-7.98 (m, 1 H), 8.09 (d, 1 H), 8.62 (d, 2H), 10.25 (s, 1 H), 12.65 (s, 1 H).MS (electrospray): m/z [M+H]+ = 371

The synthetic route of 28466-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; NICHOLS, Paula Louise; EATHERTON, Andrew John; BAMBOROUGH, Paul; JANDU, Karamjit Singh; PHILPS, Oliver James; ANDREOTTI, Daniele; WO2011/38572; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 694-48-4, The chemical industry reduces the impact on the environment during synthesis 694-48-4, name is 1,3-Dimethyl-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Put 100g (1.04mol, 1eq) of 1,3-dimethylpyrazole into the reaction bottleWith 400 mL of ethanol, 166.4 g (1.04 mol, 1.00 eq) of bromine was added dropwise with stirring at 5-10C.React at 5-10 for 4 hours,Sampling GC to check the remaining material is less than 1%, add 300mL water,Then add 200mL of saturated aqueous sodium thiosulfate solution to quench,Distilling ethanol under reduced pressure, cooling to 0 ,Filtered180.2g of 4-bromo-1,3-dimethyl-1H-pyrazole,GC purity 94.3%,The yield is 99%

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

Reference:
Patent; Xuzhou Shengyuan Chemical Co., Ltd.; Chen Hong; Yu Wanli; (8 pag.)CN111233768; (2020); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 179692-08-1, A common heterocyclic compound, 179692-08-1, name is Ethyl 4-iodo-1H-pyrazole-5-carboxylate, molecular formula is C6H7IN2O2, 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.

NaH (60% dispersion in mineral oil, 0.72 g, 18 mmol, 1.2 eq) was added in portions to a mixture of ethyl 4-iodo-1H-pyrazole-3-carboxylate (4.2 g, 15 mmol, 1.0 eq) and anhydrous THF (15 mL) at 0C. Once addition of NaH was complete, the mixture was stirred for an additional 30 min at 0C and 1h at RT. The mixture was re-cooled to 0C and then MeI (1.0 mL, 16.5 mmol, 1.1 eq) was added. When the reaction mixture solidified, the cold bath was removed and the mixture was maintained at RT for 1h. When the starting material was consumed as judged by analytical HPLC, H2O (0.5 mL) was added slowly to quench the reaction and then NaOH solution (2 M, 1.0 eq) was added slowly with stirring. The mixture was stirred at rt until hydrolysis of the ester was complete (1-2 h). The light-yellow suspension was filtered and the resulting yellow solid was collected. The filtrate was concentrated in vacuo and then washed with hexanes to remove the mineral oil. The resulting aqueous layer and solid were combined and acidified with 6N HCl to pH 12. The aqueous was extracted with EtOAc (3x). The combined organics were washed with brine, dried (Na2SO4), and concentrated to afford the title acid as a pale yellow solid that was used without further purification.

The synthetic route of 179692-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore, M.; HOLENZ, Joerg; WESOLOWSKI, Steven; HE, Yuanjun; BUeRLI, Roland; (201 pag.)WO2017/139603; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 10010-93-2,Some common heterocyclic compound, 10010-93-2, name is 3-Methyl-5-(trifluoromethyl)-1H-pyrazole, molecular formula is C5H5F3N2, 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.

EXAMPLE 2. Preparation of N-methyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-[(1R)-1-phenylpropyl]-4-thiazolecarboxamide (Compound 117) Step A: Preparation of 5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-acetic acid. A mixture of 3-methyl-5-trifluoromethylpyrazole (10.0 g, 66.7 mmol), ethyl bromoacetate (11.1 mL, 100 mmol) and potassium carbonate (18.4 g, 133 mmol) in 80 mL of N,N-dimethylformamide was stirred at ambient temperature overnight. The orange mixture was filtered, diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated under reduced pressure to give 15.7 g of the pyrazole ester. The ester, in 100 mL of tetrahydrofuran, was treated with 11 mL of a 50 % aqueous NaOH solution in 90 mL of water and stirred at ambient temperature overnight. The tetrahydrofuran was removed under reduced pressure and the aqueous solution was washed with ether and acidified with conc. HCl to pH 1 to give a precipitate. The precipitate was filtered, washed with water and dried to give 12.1 g of the title compound as a white solid. 1H NMR (Acetone-d6) delta 2.35 (s, 3H), 5.07 (s, 2H), 6.45 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methyl-5-(trifluoromethyl)-1H-pyrazole, its application will become more common.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2007/14290; (2007); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics