Tag: M.W:200-300

Synthetic Route of 37687-24-4, These common heterocyclic compound, 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate, 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 diethyl 1H-pyrazole-3,5-dicarboxylate (20.0 g, 94.2 mmol) in acetic acid (360 ml) was added dropwise sodium hypochlorite solution (220 ml, 9% in water). After stirring for 6 h at room temperature, the reaction mixture was concentrated under reduced pressure to remove acetic acid, and the remaining mixture was diluted with water (1000 ml). 1.0 M hydrochloric acid was added until pH 4 was reached, and the mixture was extracted with ethyl acetate (3 x 700 ml). The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification of the residue by flash- chromatography on silica gel (eluent: ethyl acetate/petroleum ether 1 :1) afforded the title compound. Yield: 20.0 g (76% of theory, 88% purity). 1H-NMR (300 MHz, DMSO-d6): d [ppm] = 14.93 (br. s, 1H), 4.43-4.30 (m, 4H), 1.39-1.30 (m, 6H).

Statistics shows that Diethyl 3,5-pyrazoledicarboxylate is playing an increasingly important role. we look forward to future research findings about 37687-24-4.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; MUeLLER, Steffen; SCHOHE-LOOP, Rudolf; ORTEGA, HERNANDEZ, Nuria; SUeSSMEIER, Frank; JIMENEZ NUNEZ, Eloisa; BRUMBY, Thomas; LINDNER, Niels; GERDES, Christoph; POOK, Elisabeth; BUCHMUeLLER, Anja; GAUGAZ, Fabienne, Zdenka; LANG, Dieter; ZIMMERMANN, Stefanie; EHRMANN, Alexander, Helmut, Michael; GERISCH, Michael; LEHMANN, Lutz; TIMMERMANN, Andreas; SCHAeFER, Martina; SCHMIDT, Georg; SCHLEMMER, Karl-Heinz; FOLLMANN, Markus; KERSTEN, Elisabeth; WANG, Vivian; GAO, Xiang; WANG, Yafeng; (801 pag.)WO2019/219517; (2019); A1;,
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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;,
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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

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

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;,
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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. 15802-75-2, name is 4-Iodo-3-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., SDS of cas: 15802-75-2

Compound 34H and Compound 34I: 1-[3-(Benzyloxy)propyl]-4-iodo-3-methyl-1 /-/-pyrazole and 1 -[3-(benzyloxy)propyl]-4-iodo-5-methyl-1 H-pyrazoleA mixture of 3-methyl-4-iodopyrazole (2.59 g, 12.5 mmol) and 1 -bromo-3- benzyloxypropane (3.00 g, 13.1 mmol) in DMF (1 1.4 mL) was charged with potassium carbonate (2.07 g, 15.0 mmol). The reaction mixture was allowed to stir at rt for 16 hrs overnight. The reaction mixture was quenched with water and then extracted with EtOAc. The organic layer was washed with water, brine (2x), dried over sodium sulfate, filtered, and then concentrated in vacuo to yield an oil. The crude material was purified using a Teledyne ISCO Combiflash Rf system [Heptane/EtOAc (100:0? 0:100)] to afford the title products as a mixture of regioisomers (3.60 g, 41 % combined yield). The reaction was carried onto the next step without any further purification. MS (ESI): m/z = 357.02 [M+H]+. UPLC: tR = 1.62 min (UPLC-TOF: polar_3 min).

The synthetic route of 15802-75-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSI PHARMACEUTICALS, LLC; CREW, Andrew, P.; DONG, Hanqing; FERRARO, Caterina; SHERMAN, Dan; SIU, Kam, W.; WO2012/74951; (2012); 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. 398495-65-3, name is 5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 398495-65-3

A: starting materials i) 3-[(3,3-Dimethyl-2-oxo-2,3-dihydro-lH-mdole-6-carbonyl)-amino]-4,6- dihydro-pyrrolo[3>4-c]pyrazole-l,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester3,3-Dimethyl-2-oxo-2,3-dihydro-lH-indole-6-carboxylic acid (3.0 g, 14.62 mmol) was dissolved in thionylchloride (19.1 mL, 163 mmol) and after addition of N,N- dimethylformamide (DMF) (200 muL) the mixture was refluxed for 1.5 hours. The volatiles were carefully removed under reduced pressure and the resulting 3,3- dimethyl-2-oxo-2,3-dihydro-lH-indole-6-carbonyl chloride was added portionwise to a mixture of 3-amino-4,6-dihydro-pyrrolo[3,4-c]pyrazole-l,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester (4.33 g, 14.62 mmol) in dry dichloromethane (DCM) (40 mL) and ethyl-diisopropyl-amine (DIEA) (2.53 mL, 14.62 mmol). The resulting mixture was stirred for 30 minutes, washed with water (20 mL) and brine (20 mL) and evaporated to dryness. Purification by flash chromatography over silica gel eluting with ethyl acetate/«-heptane (2:1), afforded the title compound as a white solid (5.5 g, 78 %).MS: M = 482.0 (ESI-)1H-NMR (400 MHz, DMSO): delta (ppm) = 1.28 (s, 6H), 1.34 (t, 3H), 1.46 (s, 9H),4.41 (q, 2H), 4.51 (br, 2H, rotamers), 4.60 (br, 2H, rotamers), 7.42 (m, IH), 7.47 (s, IH), 7.71 (m, IH), 10.58 (s, IH), 11.45 (s, IH)

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; F. HOFFMANN-LA ROCHE AG; WO2008/17465; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 34091-51-5, These common heterocyclic compound, 34091-51-5, name is 5-Iodo-1-methyl-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.

PREPARATION 665-lodo-1 -methyl-1 H-pyrazole-4-carbaldehydeTo a cooled (0 C) solution of 5-iodo-1 -methyl-1 H-pyrazole (1.3 g, 6.3 mmol) in dimethyl formamide (2 mL), under an atmosphere of nitrogen, was added phosphorusoxychloride (1.72 mL, 18.8 mmol, 3.0 eq.). The resulting mixture was stirred at room temperature for 4hr before partitioning between ethyl acetate (80 mL) and 2M aqueous potassium carbonate (80 mL). The aqueous layer was extracted again with ethyl acetate (80 mL). The organic extracts were combined and washed with water (3 x 50 mL) and then dried over magnesium sulphate. The resulting mixture was filtered and the filtrate evaporated under reduced pressure to give the title compound as an orange solid (0.58 g, 39%).LRMS: ESI, m/z 337 [M+H] +

The synthetic route of 34091-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BUNNAGE, Mark, Edward; COOK, Andrew, Simon; CUI, Jingrong, Jean; DACK, Kevin, Neil; DEAL, Judith, Gail; GU, Danlin; HE, Mingying; JOHNSON, Patrick, Stephen; JOHNSON, Ted, William; LE, Phuong, Thi, Quy; PALMER, Cynthia, Louise; SHEN, Hong; WO2011/138751; (2011); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 19968-17-3, name is 4-Bromo-3-(trifluoromethyl)-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. Recommanded Product: 4-Bromo-3-(trifluoromethyl)-1H-pyrazole

3-Methyl-4-nitrobenzyl chloride (0.77 g), 4-bromo-3-trifluoromethyl-lH-pyrazole (0.90 g) and po- tassium carbonate (0.57 g) were stirred in DMF (10 ml) at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate and washed with water and saturated aqueous solution of so- dium chloride. After drying the organic layer with magnesium sulfate, the solvent was distilled off under the reduced pressure and the obtained residue was purified by silica gel column chromatogra- phy to obtain 1- (3-methyl-4-nitrobenzyl)-4-bromo-3-trifluoromethyl-lH-pyrazole (0.9 g). ‘H-NMR (CDCl3, ppm): 2.58 (3H, s), 5.35 (2H, s), 7.24-7. 21 (2H, m), 7.49 (1H, s), 7. 98 (1H, d).

The synthetic route of 4-Bromo-3-(trifluoromethyl)-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AG; WO2005/95351; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 51516-67-7, 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 51516-67-7 as follows.

General procedure: Intermediate 4 (0.001mol) and 5 (0.001mol) were dissolved in pyridine, phosphorus oxychloride is slowly added dropwise under ice bath conditions, then at 40-60C reacted for 5-8h. Finally, the mixture was poured into 30mL saturated Na2CO3 solution and stirred well. After the mixture was acidified, the saturated CuSO4 solution was used to remove pyridine, which greatly improved the purity and yield of the product. The data for compounds 8I-8VI are provided in the supporting information.

According to the analysis of related databases, 51516-67-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Hao; Ren, Zi-Li; Wang, Wei; Gong, Jie-Xiu; Chu, Ming-Jie; Ma, Quan-Wei; Wang, Jie-Chun; Lv, Xian-Hai; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 81 – 87;,
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Pyrazoles – an overview | ScienceDirect Topics