Day: September 24, 2020

33821-94-2, 2-(3-Bromopropoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 10; 6-[Lambda/-(2,4-Difluorophenyl)-Lambda/-(3-hydroxypropyl)amino]-2,2-dimethyl-1, 2,3,4- tetrahydronaphthalen-1 -one; a) 6-[Lambda/-(2,4-Difluorophenyl)-W-(3-(tetrahydropyran-2-yloxy)propyl)amino]- 2,2-dimethy 1-1 ,2,3,4-tetrahydronaphthalen-1 -one; To a suspension of 6-(2,4-difluorophenylamino)-2,2-dimethyl-1 , 2,3,4- tetrahydronaphthalen-1-one (1.94 g, 6.44 mmol, obtained in example 4) in dry toluene (70 mL), sodium hydride (0.56 g, 55% dispersion in oil, 12.83 mmol) and 15-crown-5 (47 mg, 0.21 mmol) were added under argon and the mixture was stirred at room temperature for 20 min. Then, 3-bromopropanol tetrahydropyranyl EPO ether (1.44 g, 6.44 mmol) was added and the mixture was heated at 90 0C for 4 h. It was allowed to cool and diluted with EtOAc and saturated NaHCO3. The phases were separated and the aqueous phase was reextracted with EtOAc. The combined organic phases were dried over Na2SO4 and the solvent was evaporated to afford the desired compound (quantitative yield). LC-MS (method 1): tR = 11.98 min; m/z = 444.2 [M+H]+., 33821-94-2

33821-94-2 2-(3-Bromopropoxy)tetrahydro-2H-pyran 2777988, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; J. URIACH Y COMPANIA S.A.; WO2007/337; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.693287-79-5,tert-Butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate,as a common compound, the synthetic route is as follows.

Intermediate 31: 1,1-Dimethylethyl 2-(2,5-dichloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate. [Show Image] To a solution of Intermediate 26 (3.6 g, 16.8 mmol) in dry EtOH (60 mL), 2,4,5-trichloropyrimidine (ALDRICH, 3.4 g, 18.5 mmol) and DIPEA (FLUKA, 8.5 mL, 50 mmol) were added and the resulting reaction mixture was refluxed for 3h, then stirred at room temperature for 3 days. In order to drive the reaction to completion the reaction mixture was refluxed for further 7h, then stirred at room temperature for 12 h. The mixture was concentrated under reduced pressure and the residue partitioned between DCM and 1M ammonium chloride. The organic layer was treated with brine and dried over anhydrous MgSO4. The residue was purified by flash chromatography (eluent: Hex/AcOEt mixtures 49:1 to 1:1) to give the title compound. 1H NMR (300 MHz, DMSO-d6) delta ppm: 9.80 (s, 1H), 8.28 (s, 1H), 4.75- 4.56 (m, 1H), 3.96- 3.82 (m, 2H), 3.46- 3.31 (m, 2H), 1.82-1.25 (m, 13H)., 693287-79-5

The synthetic route of 693287-79-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP; EP1918284; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

Cap- 188, step aTo a solution of 2,2-dimethyldihydro-2H-pyran-4(3H)-one (2 g, 15.60 mmol) in 50 niL of MeOH was slowly added sodium borohydride (0.649 g, 17.16 mmol). The resulting mixture was stirred at room temperature for 3 hours. To the mixture was then added 1 N HCl aqueous solution until it crosses into acidic pH range and then extracted with EtOAc (3X). The combined organic layers were dried withMgS04 and concentrated to afford Cap-188, step a (1.9 g) as clear oil. The product was used in the next step without purification. XH NMR (400 MHz, CDCI3) delta ppm 3.91 – 4.02 (1 H, m), 3.79 – 3.86 (1 H, m), 3.63 (1 H, td, J=12.05, 2.51 Hz), 1.82 – 1.93 (2 H, m), 1.40 – 1.53 (1 H, m), 1.29 – 1.38 (1 H, m), 1.27 (3 H, s), 1.20 (3 H, s), 1194-16-7

The synthetic route of 1194-16-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BELEMA, Makonen; SRINIVASU, Pothukanuri; BENDER, John A.; LOPEZ, Omar D.; CHEN, Qi; RAMPULLA, Richard A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; MEANWELL, Nicholas A.; WO2012/21591; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

873397-34-3,873397-34-3, Tetrahydro-2H-pyran-3-carboxylic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of tetrahydro-2H-pyran-3-carboxylic acid:DCC (7.85 g, 38.1 mmol) was added to tetrahydro-2H-pyran-3-carboxylic acid (4.5 g, 34.6 mmol) in THF (100 mL) at 0 ¡ãC. The reaction mixture was stirred at room temperature for 1 h and cooled down to 0 ¡ãC. N-Hydroxysuccinimide (4.78 g, 41.5 mmol) was added and stirring was continued overnight at room temperature. The reaction mixture was filtered, the solvent was evaporated, and the residue was purified by column chromatography (silica gel, EtOAc/Hept, 1 :1-1 :0) to prepare 2,5-dioxopyrrolidin-l-yl tetrahydro-2H-pyran-3-carboxylate (6.5 g, 83percent yield). 1H NMR (300 MHz, CDCI3/TMS): delta 4.14-4.06 (m, 1H), 3.88-3.79 (m, 1H), 3.71-3.64 (m, 1H), 3.54-3.44 (m, 1H), 2.99-2.89 (m, 1H), 2.81 (s, 4H), 22.2-2.14 (m, 1H), 1.95-1.84 (m, 1H), 1.78-1.64 (m, 3H).

The synthetic route of 873397-34-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew; WO2012/40230; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4295-99-2,4-Cyanotetrahydro-4H-pyran,as a common compound, the synthetic route is as follows.

Step 1: To an oven-dried, nitrogen-cooled flask was added Pd2(dba)3 (96 mg, 0.10 mmol), BINAP (131 mg, 0.2 10 mmol), and THF (2 mL). The mixture was stirred for 10 mm followed by the addition of di-tert-butyl 8-bromo-5H-benzo [b]pyrido [2,3 -e] [1 ,4]diazepine-6, 11- dicarboxylate (500 mg, 1.05 mmol), tetrahydro-2H-pyran-4-carbonitrile (520 mg, 4.68 mmol), and lithium hexamethyldisilazide (0.5 M in THF, 9.2 mL, 4.6 mmol). The reaction mixture washeated to 80C for 24 h, and then cooled to room temperature. The reaction mixture was dilulted with 1:1 DCM:EtOAc (50 mL), and filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was dissolved in DCM (2 mL), and TFA (2 mL) was added. The reaction mixture was stirred for an 3 h, and then concentrate under reduced pressure. The residue was purified by reverse phase HPLC (acetonitrile/water, with 0.1% TFA modifier) to thetitle compound. MS: 307 (M + 1).

4295-99-2, As the paragraph descriping shows that 4295-99-2 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; FISCHER, Christian; BOGEN, Stephane, L.; CHILDERS, Matthew, L.; LLINAS, Francesc Xavier Fradera; ELLIS, J. Michael; ESPOSITE, Sara; HONG, Qingmei; HUANG, Chunhui; KIM, Alexander, J.; LAMPE, John, W.; MACHACEK, Michelle, R.; MCMASTERS, Daniel, R.; OTTE, Ryan, D.; PARKER, Dann, L., Jr.; REUTERSHAN, Michael; SCIAMMETTA, Nunzio; SHAO, Pengcheng, P.; SLOMAN, David, L.; UJJAINWALLA, Feroze; WHITE, Catherine; WU, Zhicai; YU, Yang; ZHAO, Kake; GIBEAU, Craig; BIFTU, Tesfaye; BIJU, Purakkattle; CHEN, Lei; CLOSE, Joshua; FULLER, Peter, H.; HUANG, Xianhai; PARK, Min, K.; SIMOV, Vladimir; WITTER, David, J.; ZHANG, Hongjun; (297 pag.)WO2016/89797; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

14774-37-9, Tetrahydropyran-4-methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0217] A solution of (tetrahydro-pyran-4-yl)-methanol (1.0 g, 8.61 mmol, prepared according to WO 99/00385) in methylene chloride (30 mL) at 25 C. was treated with 4-(dimethylamino)pyridine (1.17 g, 9.47 mmol) and p-toluenesulfonyl chloride (1.64 g, 8.61 mmol) and then was allowed to stir at 25 C. overnight. The reaction was then transferred to a separatory funnel and washed with a 1N aqueous hydrochloric acid solution (10 mL), a saturated aqueous sodium bicarbonate solution (10 mL), and a saturated aqueous sodium chloride solution (10 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 75/25 hexanes/ethyl acetate) afforded toluene-4-sulfonic acid tetrahydro-pyran-4-yl methyl ester (1.77 g, 76%) as a colorless oil. [0218] A solution of toluene-4-sulfonic acid tetrahydro-pyran-4-yl methyl ester (1.77 g, 6.55 mmol) and sodium iodide (2.85 g, 18.99 mmol) in acetone (26 mL) was heated to 60 C. for 16 h. The resulting suspension was then cooled to 10 C. and filtered. The salts were rinsed with cold acetone (5 mL), and the filtrate and washings were concentrated in vacuo to a thick slurry. This slurry was treated with methylene chloride (10 mL). The resulting precipitate was removed by filtration and was washed with methylene chloride (10 mL). The filtrate and washings were then dried over magnesium sulfate, filtered through a pad of silica gel, and then concentrated in vacuo to afford 4-iodomethyl-tetrahydro-pyran as a light yellow oil. [0219] A solution of diisopropylamine (0.33 mL, 2.38 mmol) in tetrahydrofuran (6 mL) cooled to -78 C. under an argon atmosphere was treated with a 2.5M solution of n-butyllithium in hexanes (0.95 mL, 2.38 mmol). The reaction mixture was stirred at -78 C. for 15 min, after which time, a solution of (3-chloro-4-methylsulfanyl-phenyl)-acetic acid methyl ester (prepared as in Example 4, 500 mg, 2.17 mmol) in tetrahydrofuran (1 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (0.5 mL) was slowly added via a cannula. The greenish yellow solution was allowed to stir at -78 C. for 1 h, after which time, a solution of 4-iodomethyl-tetrahydro-pyran (588 mg, 2.60 mmol) in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (0.5 mL) was added via a cannula. The reaction mixture was then allowed to warm to 25 C., where it was stirred for 16 h. The reaction mixture was then quenched by the addition of a saturated aqueous ammonium chloride solution (30 mL). This solution was extracted with ethyl acetate (3¡Á20 mL). The combined organic layers were washed with a 10% aqueous sulfuric acid solution (2¡Á50 mL) and a saturated aqueous sodium bicarbonate solution (2¡Á50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 75/25 hexanes/ethyl acetate) afforded 2-(3-chloro-4-methylsulfanyl-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (431 mg, 61%) as a yellow oil: EI-HRMS m/e calcd for C16H21ClO3S (M+) 328.0900, found 328.0898. [0220] A solution of 2-(3-chloro-4-methylsulfanyl-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (200 mg, 0.61 mmol) in formic acid (0.23 mL) and tetrahydrofuran (0.5 mL) cooled to 0 C. was treated with a 30% aqueous hydrogen peroxide solution (0.35 mL, 3.04 mmol). The reaction was slowly warmed to 25 C. where it was stirred for 16 h. The reaction mixture was then cooled to 0 C., quenched with a saturated aqueous sodium sulfite solution, and then extracted with ethyl acetate (3¡Á20 mL). The organics were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, 60/40 hexanes/ethyl acetate) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (190 mg, 87%) as a colorless oil: (ES)+-HRMS m/e calcd for C16H21ClO5S (M+Na)+ 383.0690, found 383.0692. [0221] A

14774-37-9, The synthetic route of 14774-37-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Corbett, Wendy Lea; Grimsby, Joseph Samuel; Haynes, Nancy-Ellen; Kester, Robert Francis; Mahaney, Paige Erin; Racha, Jagdish Kumar; Sarabu, Ramakanth; Wang, Ka; US2003/225283; (2003); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.85064-61-5,Tetrahydropyranyl-4-acetic acid,as a common compound, the synthetic route is as follows.

Example 1-29 l-(l-(4-Chloro-2-fluorobenzyl)-3-(trif uoromethyl)-4,5-dihydro-lH-pyrazolo[3,4- c]pyridin-6(7H)-yl)-2-(tetrahydro-2H-pyran-4-yl)ethanone To a solution of 2-(tetrahydro-2H-pyran-4-yl)acetic acid (52 mg, 0.36 mmol, 1.2 eq), 1- (4-chloro-2-fluorobenzyl)-3-(trifluoromethyl)-4,5,6,7-tetrahydro-lH-pyrazolo[3,4- c]pyridine hydrochloride (Intermediate 2-1) (110 mg, 0.30 mmol, 1.0 eq) and HATU (171 mg, 0.45 mmol, 1.5 eq) in DMF (2 mL) was added N,N-diisopropylethylamine (77 mg, 0.60 mmol, 2.0 eq). The mixture was stirred at room temperature for 16 h and diluted with water (100 mL). The mixture was extracted with EtOAc (100 mLX 3). The combined organic layers were dried over anhydrous sodium sulfate and concentrated. The residue was purified by prep-HPLC (TFA method) to afford l-(l-(4-chloro-2- fluorobenzyl)-3-(trifluoromethyl)-4,5-dihydro-lH-pyrazolo[3,4-c]pyridin-6(7H)-yl)-2- (tetrahydro-2H-pyran-4-yl)ethanone as a yellow oil (131 mg, yield 95percent). 1H NMR (400 MHz, Methanol-d4) delta: 7.31-7.16 (m, 3H), 5.41-5.36 (m, 2H), 4.71-4.70 (m, 2H), 3.92- 3.87 (m, 2H), 3.82-3.75 (m, 2H), 3.45-3.35 (m, 2H), 2.76-2.63 (m, 2H), 2.45-2.34 (m, 2H), 2.06-1.92 (m, 1H), 1.68-1.59 (m, 2H), 1.39-1.26 (m, 2H); LCMS (ESI) m/z 459.9 [M+H]+, 85064-61-5

As the paragraph descriping shows that 85064-61-5 is playing an increasingly important role.

Reference£º
Patent; BIOGEN MA INC.; KUMARAVEL, Gnanasambandam; PENG, Hairuo; XIN, Zhili; WO2015/188051; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

2081-44-9, To a solution of tetrahydropyran-4-ol (1.0 g, 9.8 mmol) in DCM (5 mL) was added Et3N (triethylamine; 2.73 mL, 20 mmol). To the mixture was added a solution of methanesulfonyl chloride (0.91 mL, 12 mmol) in DCM (dichloromethane; 5 mL) at 0 C. The mixture was stirred at 0 C for 1 hour. Upon completion, the reaction mixture was treated with water (5 mL), and extracted with DCM (10 mL x 3). The organic layers were combined, washed with brine (10 mL x 3), dried over Na2S04, filtered and concentrated under reduced pressure to afford tetrahydropyran-4-yl methanesulfonate (1.3 g, crude) as a white solid, which was used directly in the next step.

2081-44-9 Tetrahydro-2H-pyran-4-ol 74956, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; SYROS PHARMACEUTICALS, INC.; ZHANG, Yi; AUSTGEN, Kathryn; CHUAQUI, Claudio Edmundo; MALOJCIC, Goran; SINKO, William; CIBLAT, Stephane; JAMES, Clint; GUAN, Huiping Amy; SAVOIE, Tracey Lodie; (179 pag.)WO2019/14513; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1228779-96-1, 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 3- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy) -4′- (2-phenylpyrrolidin-1-yl) -2′, 3′, 4′, 5′-tetrahydro- [1, 1′-biphenyl] -4-carboxylic acid (200 mg, 0.416 mmol), 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzenesulfonamide (131 mg, 0.416 mmol), EDCI (120 mg, 0.624 mmol), DMAP (76 mg, 0.624 mmol) and DIPEA (161 mg, 1.247 mmol) in DCM (10 mL) was stirred at ambient temperature for 20 h. The reaction solution was concentrated and purified by pre-HPLC to give the product (30 mg). 1H NMR (DMSO-d 6) delta ppm: 11.63 (s, 1H), 8.46 (s, 2H), 7.96 (t, J = 4.0 Hz, 1H), 7.73 (d, J = 8.0 Hz, 1H), 7.55-6.97 (m, 11H), 6.72 (s, 1H), 6.34 (s, 1H), 5.98-5.86 (m, 1H), 3.84 (dd, J = 12.0, 4.0 Hz, 2H), 3.28-3.22 (m, 5H), 2.33-1.83 (m, 10H), 1.61-1.58 (d, J = 12.0 Hz, 4H), 1.29-1.18 (m, 3H). MS (ESI) m/e [M+1] + 777.2.

1228779-96-1, 1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BEIGENE, LTD.; GUO, Yunhang; XUE, Hai; WANG, Zhiwei; SUN, Hanzi; (493 pag.)WO2019/210828; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

Compound 18-2 was dissolved in dichloromethane, (3 eq) EDCI, (0.3 eq) DMAP was added, and stirred at room temperature for half an hour, then compound 1-5 (0.8 eq) was added.It is then reacted at room temperature for 6-8 hours. After the reaction is completed, the reaction is quenched with water.Extract three times with dichloromethane, and combine the organic phases with saturated brine.After drying anhydrous sodium sulfate, mix the sample on the column.CH2Cl2: MeOH = 100:1 – 30:1 gave compound S18., 1228779-96-1

The synthetic route of 1228779-96-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhang Ao; Tan Wenfu; Liu Xiaohua; Huang Wenjing; Zhang Yu; Yang Jun; (37 pag.)CN110143974; (2019); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics