Tag: M.W:200-300

Application of 1280210-79-8,Some common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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 stirred solution of /erf-butyl 2,6^hydropyrrolo[3,4-c]pyrazole-5(4 /)- carboxylate (20 g, 96 mmol) in DMF (200 mL) at 0 C was added sodium hydride (4.21 g, 105 mmol). After stirring for 1 h at RT, 2-trimetbylsilylethoxymethyl chloride (SEM-C1) (4.65 mL, 26.3 mmol) was added. The resulting mixture was stirred at RT overnight. The mixture was quenched with saturated NuEta4OmicronEta, and the solvents were removed. The residue was diluted with ethyl acetate (500 mL), washed with water, brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on a silica gel Biotage 65i column, eluting with 0 to 20% ethyl acetate in hexanes to give the title compound as a colorless gum. LC-MS: 340.1 (Mu+Eta)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HICKS, Jacqueline, D.; BIFTU, Tesfaye; CHEN, Ping; QIAN, Xiaoxia; WILKENING, Robert, R.; WO2011/146358; (2011); A1;,
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

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 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. 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate

2D (3.5 g, 16.7 mmol) was dissolved in tetrahydrofuran (35 mL)Cooled to 0 C,60% sodium hydride (1.0 g, 25.4 mmol) was added,After reaction for 30 minutes, methylsulfonyl chloride (2.9 g, 25.4 mmol) was added and reacted for 1 hour.The reaction mixture was quenched with water (10 mL) and extracted with ethyl acetate (50 mL x 2). The organic layers were combined and the organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (petroleum ether / Ethyl acetate (v / v) = 1: 1) to give 2E as a white solid (2.1 g, yield 44%).

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 1280210-79-8.

Reference:
Patent; SICHUAN HAISCO PHARMACEUTICAL CO., LTD; ZHANG, CHEN; FAN, JIANG; LEI, MING; WEI, YONG-GANG; (61 pag.)TW2017/8223; (2017); A;,
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. 398491-61-7, name is tert-Butyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-5(1H,4H,6H)-carboxylate, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

Example 1 : beta.beta-dimethyl-W-ttrans^-phenylcyclopropyll-S-tthienoES.Z-dlpyrimidin^-ylaminoJAbeta- dihydropyrrolo[3,4-c]pyrazole-5(1W)-carboxamide; .Preparation of Compound 1a: Lambda/-(6,6-dimethyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3- yl)thieno[3,2~d]pyrimidin-4-amine.; To a stirring solution of ferf-butyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)- carboxylate (0.62g, 2.46 mmol) in DMA (3mL) was added 4-chlorothieno[3,2-c/]pyrimidine(0.44g, 1.05eq) and 4N HCI solution in 1,4-dioxane (0.65ml, 1.05eq). The resulting mixture was heated to 1400C for 0.5 EPO hours in microwave reactor. It was cooled to room temperature and the compound 1a was precipitated. Filtration and washing with CH2CI2 provided compound 1a as a yellow solid (0.48 g, 68% yield). Compound 1a was directly carried onto the next reaction without further purification. LCMS (API-ES, M+H+): 287.0. To a stirring mixture compound 1a(0.12g, 0.42mmol), and TEA (0.117ml, 2eq) in DMSO (1ml) and CH2CI2 (2ml) was added trans-2-phenylcyclopropyl isocyanate (0.068ml, 1.1eq). The resulting mixture was stirred at room temperature for 2h. The reaction mixture was purified by prep-HPLC to provide the title compound 1 as a white solid (0.019g, 10%). 1H NMR (CD3OD) delta: 1.06 (m, 1H), 1.11 (m, 1H), 1.68 (d, J=4.04 Hz, 6 H), 1.98 (m, 1 H), 2.69 (m, 1 H), 4.43 (s, 2 H), 7.01 – 7.07 (m, 3 H), 7.11 – 7.17 (m, 2 H), 7.34 (d, J=5.56 Hz, 1 H), 8.04 (d, J=5.31 Hz, 1 H), 8.59 (s, 1 H). Anal. (C23H23N7OS-CSHOACO-SH2O) C, H, N. HPLC: >95% purity.

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.; WO2006/72831; (2006); 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. 706819-66-1, name is 2-Bromo-1-(1-methyl-1H-pyrazol-4-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H7BrN2O

2-bromo-1-(1-methyl-1H-pyrazol-4-yl)-ethanone (0.5 g; 2.46 mmol) in DMF (10 mL) were added to potassium phtalimide (0.46 g; 2.46 mmol). The reaction mixture wasstirred at RT for 5h, poured into water-ice and EtOAc was added. The organic layer was separated, washed with water, brine, dried over Mg504, filtered and evaporated till dryness. The residue was purified by chromatography over silica gel (irregular SiOH 15-40.im, 24g; mobile phase: 97% DCM, 3% MeOH (+10% NH4OH)). The pure fractions were collected and evaporated to dryness yielding 460 mg (69%) of intermediate 86.

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 706819-66-1.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PILATTE, Isabelle, Noelle, Constance; PATRICK, Aaron, Nathaniel; (250 pag.)WO2018/50686; (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. 50877-42-4, name is 1-Benzyl-4-iodo-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 50877-42-4

b) 1 -Benzyl- 1 H -pyrazole-4 -carbaldehyde (A 148) 1-Benzyl-4-iodo-1 H-pyrazole A147 (859 mg, 3.02 mmol) in THF (5 mL) was cooled to 0 C under nitrogen before a 2.0 M solution of isopropylmagnesium chloride in THF (1.66 mL, 3.33 mmol) was added. After 1 hour, DMF (0.5 mL) was added. The mixture was stirred for 30 minutes at 0 C then a further 30 minutes at room temperature. The mixture was quenched with a saturated aqueous solution of ammonium chloride (10 mL), diluted with water (20 mL) and extracted with CHCI3 (3 chi 25 mL). The pooled organics were washed with brine (50 mL), dried with sodium sulfate and concentrated in vacuo. The crude material was purified by column chromatography (12 g Si02 cartridge, 0-50% EtOAc in hexanes) to give the title compound as a colourless oil (170 mg, 30%). H NMR (400 MHz, CDCI3) delta 9.83 (s, 1 H), 8.00 (s, 1 H), 7.88 (s, 1 H), 7.42-7.33 (m, 3H), 7.29-7.25 (m, 2H), 5.33 (s, 2H). LCMS-B: rt 3.10 min, m/z (positive ion) 187.1 [M+H]+.

According to the analysis of related databases, 50877-42-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LTD; STUPPLE, Paul Anthony; WALKER, Scott Raymond; PINSON, Jo-Anne; LAGIAKOS, Helen Rachel; LUNNISS, Gillian Elizabeth; HOLMES, Ian Peter; STUPPLE, Alexandra Elizabeth; BERGMAN, Ylva Elisabet; FOITZIK, Richard Charles; KERSTEN, Wilhelmus Johannes Antonius; CAMERINO, Michelle Ang; WO2014/128465; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products 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.

A solution of compound 2a (2 g, 9.43 mmol); K2CO3 (2.6 g, 18.86 mmol) and 1, 3 bromochloropropane (7.4 mL, 47.16 mmol) in acetonitrile (60 mL) was refluxed for 1 h. The reaction mixture was cooled; filtered and extracted with ethyl acetate (2 x 150 mL), dried over anhydrous sodium sulphate, filtered and the filtrate was evaporated to dryness to afford compound 3c (2.1 g, 67%). MS (ES+) m/z: 334.

The synthetic route of 37687-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Surase, Yogesh B.; Samby, Kirandeep; Amale, Sagar R.; Sood, Ruchi; Purnapatre, Kedar P.; Pareek, Pawan K.; Das, Biswajit; Nanda, Kamna; Kumar, Subodh; Verma, Ashwani K.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3454 – 3459;,
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. 3528-45-8, name is 1-(4-Methoxybenzyl)-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., Product Details of 3528-45-8

To an ice-cooled solution of 2-(4-methoxy-benzyl)-2eta-pyrazol-3-ylamine (406 mg, 2.0 mmol, 1.0 eq.) in DCM (5 mL), DIPEA (0.52 ml, 3.0 mmol, 1.5 eq.) was added.A solution of bromoacetyl bromide (0.19 ml, 2.2 mmol, 1.1 eq.) in DCM (2 mL) was added dropwise. The cooling bath was removed and the brown solution was stirred at r.t. for 1.5 hours. The solution was diluted with AcOEt (75 mL), washed with sat. aq.NaHCO3 soln. (1 x 40 mL), with sat. aq. NaCl soln. (1 x 40 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by CC (SiO2, AcOEt/Hept 1 :1 to6:4) to give the desired bromide as a beige solid.LC-MS (A): tR = 2.60 min; [M-H]+ = 322.3.

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; ACTELION PHARMACEUTICALS LTD; WO2009/150614; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics