Day: November 3, 2020

137052-08-5, 1-(Tetrahydro-2H-pyran-4-yl)ethanone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 1-tetrahydro-2H-pyran-4-ylethanone (351 mg; 2.74 mmol), intermediate11(600 mg; 1.83 mmol), Ti(OiPr)4 (870 jiL; 2.92 mmol) in EtOH (3 mL) was stirred for2 hours at 45C. Additional EtOH (18 mL) and NaBH4 (138 mg; 3.65 mmol) were added.The reaction mixture was stirred at room temperature for 5 hours. The reaction mixturewas diluted with DCM and poured onto a 10% aqueous solution of K2C03. The insolublematerial was removed by filtration over celite. The organic layer was separated, washedwith water, dried over MgSO4, filtered and evaporated to dryness. The residue waspurified by chromatography over silica gel (irregular SiOH, 24g; mobile phase : gradientfrom 0% NH4OH, 0% MeOH, 100% DCM to 1% NH4OH, 10% MeOH, 90% DCM).The fractions containing the product were collected and evaporated to dryness yielding487 mg (60%) of compound 145. The enantiomers of compound 145 were separated bychiral SFC (CHIRALPAK AD-H 5.im 250*30mm; mobile phase: 70% C02, 30%mixture of EtOH/iPrOH 50/50 v/v). The fractions containing the products were collectedand evaporated to dryness. The residues were freeze dried from from water/ACN (80/20;10 mL)yielding 171mg (21%) of compound 154 and 178mg (22%) of compound 155.

137052-08-5, The synthetic route of 137052-08-5 has been constantly updated, and we look forward to future research findings.

Reference£º
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;,
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.951127-25-6,tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.,951127-25-6

22c (0.270 g, 0.720 mmol) was dissolved in dimethylacetamide (5 mL) at room temperature,Intermediate 1 (0.170 g, 0.540 mmol) was added and stirred at room temperature for 1 hour.Sodium tris (acetoxy) borohydride (0.192 g, 0.910 mmol) was added to the reaction solution, and the reaction was stirred at room temperature for 16 hours.The reaction system was cooled to 0 C, water (10 mL) was added successively, and the pH was adjusted to 8 with aqueous ammonia (1 mL) to precipitate a white solid.The reaction solution was filtered and the cake was washed successively with water (5 mL x 3), petroleum ether (10 mL x 1).The filter cake was dried to give a pale white solid 22d (0.220 g, yield 79.7%).

As the paragraph descriping shows that 951127-25-6 is playing an increasingly important role.

Reference£º
Patent; Sichuan Haisco Pharmaceutical Co.,Ltd; FAN, JIANG; CHEN, QINGPING; JIANG, WEI; ZHENG, SUXIN; YE, FEI; (128 pag.)TW2017/8221; (2017); A;,
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.1172623-99-2,tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

Tert-butyl (2R,3S)-2-(2,5-difluorophenyl)-5-hydroxyltetrahydro-2H-pyran-3-ylcarbamate (2.33 g, 7.08 mmol) was dissolved in a mixed solution of 24 mL acetonitrile, 4 mL water and 4 mL acetic acid. Thereto was added an aqueous solution (4 mL) of ruthenium chloride hydrate (3.7 mg, 0.0142 mmol), and cooled to 0 C. Sodium bromate (535 mg, 3.54 mmol) was added, and stirred at low temperature for about 1.5 hours until the raw materials were completely reacted. To the reaction solution was added 120 mL water, stirred at 0 C overnight, and extracted with dichloromethane. The organic phase was washed with water, dried and concentrated, and then the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 10:1) to give the intermediate 1 tert-butyl (2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-ylcarbamate (1.71 g) as a white solid in 74% yield. 1H-NMR (400 MHz, CDCl3): delta=7.22(1H, m), 7.00(1H, m), 4.82 (1H, m), 4.63 (1H, m), 4.29(1H, d, J=16.2Hz), 4.11(1H, d, J=16.4Hz), 4.05 (1H, m), 3.05(1H, m), 2.85 (1H, m), 1.30 (9H, s).

1172623-99-2, 1172623-99-2 tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate 86713019, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Centaurus BioPharma Co., Ltd.; Chai Tai Tianqing Pharmaceutical Group Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; XU, Xinhe; SHEN, Yu; XIAO, Dengming; LUO, Hong; PENG, Yong; HAN, Yongxin; ZHANG, Aiming; YANG, Ling; (51 pag.)EP3257857; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

624734-17-4,624734-17-4, 3-Methoxydihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Toa solution of ((3aS,5S,6aR)-5-aminohexahydro-2H-cyclopenta[b]furan-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone (119 mg, 0.33 mmol, 1 eq) in DCM at rtwas added acetic acid (0.01 mL, 0.17 mmol, 0.5 eq),3-methoxytetrahydro-4H-pyran-4-one (131 mg, 1.0 mmol, 3 eq) and sodiumtriacetoxyborohydride (355 mg, 1.67 mmol, 5 eq). After stirring overnight, saturated NaHCO3was added, the solution extracted with DCM, the organics combined, dried overMgSO4, and concentrated.Purification by chromatography (12 g) eluting with 4 to 8% methanol/DCMwith ammonia afforded compound 2a ((3aS,5S,6aR)-5-((3-methoxytetrahydro-2H-pyran-4-yl)amino)hexahydro-2H-cyclopenta[b]furan-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone(83 mg, 50%). 1H NMR (CHLOROFORM-d)d: 8.72 (br. s., 1H), 7.70 (br. s., 1H), 4.98 -5.14 (m, 1H), 4.70 – 4.89 (m, 2H),3.80 – 4.18 (m, 5H), 3.25 – 3.75 (m, 8H), 3.07 – 3.24 (m, 2H), 2.53 – 2.89 (m,1H), 2.01 – 2.48 (m, 4H), 1.39 – 1.88 (m, 5H).ESI-MS (m/z): Calculated for C23H30F3N3O4:470.2 (M+1); found: 470.2.

624734-17-4 3-Methoxydihydro-2H-pyran-4(3H)-one 23533610, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Winters, Michael P.; Teleha, Christopher A.; Kang, Fu-An; McComsey, David; O’Neill, John C.; Hou, Cuifen; Kirchner, Thomas; Wang, Ping; Johnson, Dana; Sui, Zhihua; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2137 – 2140;,
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.156353-01-4,N-Methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide,as a common compound, the synthetic route is as follows.

[0240] A flask was charged with N-methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide 2 (11.7 g, 67.5 mmol) andTHF (350 mL). The resulting mixture was immersed in a cooling bath at -60C, and methylmagnesium bromide (3.0 Min ether, 33.8 mL, 101.4 mmol) was added via syringe over ? 8 min. The temperature of the bath was allowed to rise to0 C over 6h. At that time, the reaction was diluted with water and EtOAc and stirred vigorously for 10 min. The phaseswere separated, and the aqueous layer was extracted with EtOAc. The organic portions were combined, washed withbrine, dried over MgSO4, filtered, and concentrated. The crude residue was subjected to column chromatography (120g silica, 80 mL/min, 0% to 100% EtOAc/hexanes) to give 4-acetyltetrahydro-4H-pyran 3 (7.05 g, 55.0 mmol, 81%). 1HNMR (400 MHz, CDCl3) for 3: delta 3.95 (ddd, J = 11.6, 4.4, 2.8 Hz, 2 H), 3.38 (dt, Jd = 2.8 Hz, Jt = 11.6 Hz, 2 H), 2.50 (m,1 H), 2.12 (s, 3 H), 1.75 (m, 2 H), 1.65 (m, 2 H). LCMS for 3 (conditions D): tR = 0.83 min, m/e = 129.4 (M+H, base)., 156353-01-4

As the paragraph descriping shows that 156353-01-4 is playing an increasingly important role.

Reference£º
Patent; Merck Sharp & Dohme Corp.; ISERLOH, Ulrich; STAMFORD, Andrew, W.; CUMMING, Jared, N.; (63 pag.)EP2485920; (2016); B1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

53911-68-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.53911-68-5,4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

3-(4-Chlorophenyl)glutaric anhydride (0.45 g) was added with stirring at rt to the solution of commercial 4-tbutyl-1,2-phenylenediamine (0.33 g) in dichloromethane (3 ml). After 1 h at rt the precipitate is collected by suction filtration, washed with dichloromethane, and dried in vacuo to give a mixture of regioisomeric amides (0.63 g) as light grey solid. The solid was suspended in 1,4-dioxane (2 ml) and 4M HCl in 1,4-dioxane (3 ml) was added. The solution is heated to reflux for 1.5 h. From the solution all volatiles are removed at the water aspirator and the residue is recrystallised from acetone /ethyl acetate to give 4-(5-tbutyl-2-benzimidazolyl)-3-(4-chlorophenyl)butanoic acid HCl (0.45 g) as light grey solid.1H-NMR (500 MHz, DMSO-d6)): delta (ppm)=1.32 (s, 9H), 2.71 (dd, J=16.2, 8.6 Hz, 1H), 2.81 (dd, J=16.2, 6.1 Hz, 1H), 3.47 (dd, J=15.0, 9.4 Hz, 1H), 3.56 (dd, J=15.0, 6.7 Hz, 1H), 3.89 (m, 1H), 7.30 (d, J=8.5 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H), 7.56 (dd, J=8.7, 1.7 Hz, 1H), 7.59 (d, J=1.0 Hz, 1H), 7.63 (d, J=8.7 Hz, 1H).13C-NMR and DEPT (125 MHz, DMSO-d6): delta (ppm)=31.11 (3CH3), 32.31 (CH2), 34.74 (C), 39.15 (CH), 109.32 (CH), 113.12 (CH), 123.56 (CH), 128.35 (2CH), 128.51 (C), 129.18 (2CH), 130.64 (C), 131.43 (C), 140.67 (C), 148.65 (C), 151.53 (C), 172.09 (CO). One carbon signal missing.

The synthetic route of 53911-68-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

To a 500 mL round-bottom flask was added 2,2-dimethyloxan-4-one 329a (10 g,78.02 mmol, 1.00 equiv.) and methanol (100 mL). NaBH4 (5.9 g, 155.96 mmol, 2.00 equiv.)5 was added in several batches at 0C. The resulting mixture vas stirred at room temperaturefor 3 h, then diluted with 200 mL of EA, vvashed vvith brine (l 00 mL x 2), dried overanhydrous sodium sulfate, and concentrated under vacuum The residue vvas purified by silicagel column chromatography eluting with ethyl acetate in petroleum ether (0% tolOO%) togive 2,2-dirnethyloxan-4-ol 329b (9 g, 89%) as a light yellow oil., 1194-16-7

1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); 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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

To a solution of 7-(3-hydroxyphenyl)-5-methyl-2-((4-(methylsulphonyl)piperazin-1- yl)methyl)thieno[3,2-c]pyridin-4(5H)-one (for a preparation see Example 10, 17 mg, 0.039 mmol) and 4-(bromomethyl)tetrahydro-2H-pyran (21 .06 mg, 0.1 18 mmol) in A/,A/-dimethylformamide (2 mL) was added potassium carbonate (16.26 mg, 0.1 18 mmol). The resulting mixture was stirred at 100 C for 3 hours, whereupon it was allowed to cool to room temperature. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted 3 times with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 2-10% methanol in dichloromethane. The appropriate fractions were combined and concentrated in vacuo to give 5-methyl-2-((4-(methylsulphonyl)piperazin-1-yl)methyl)-7-(3- ((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)thieno[3,2-c]pyridin-4(5H)-on (13 mg, 0.025 mmol, 65%). LCMS (2 min, Formic Acid): Rt = 0.80 min, MH+ = 532

125552-89-8, 125552-89-8 4-(Bromomethyl)tetrahydropyran 2773286, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXOSMITHKLINE LLC; AMANS, Dominique; BAMBOROUGH, Paul; BIT, Rino, Antonio; BROWN, John, Alexander; CAMPBELL, Matthew; LINDON, Matthew, John; SHIPLEY, Tracy, Jane; THEODOULOU, Natalie, Hope; WELLAWAY, Christopher, Roland; WESTAWAY, Susan, Marie; WO2014/78257; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4295-99-2, 4-Cyanotetrahydro-4H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tetrahydro-2H-pyran-4-carbonitrile (2 g, 18.00 mmol) in tetrahydrofuran (10 mL) at 0 – 5 C was added slowly LHMDS (21.59 mL, 21.59 mmol). The mixture was stirred for 1.5 hrs at 0 C. lodomethane (3.37 mL, 54.0 mmol) was added slowly and stirring was continued for 30 min at ~0 C and then for ~2 hrs at room temperature. The mixture was cooled to 0 C and carefully diluted with 1 N aqueous hydrochloride solution (30 mL) and EtOAc (5 mL) and concentrated under reduced pressure. The residue was taken up in diethylether and the separated organic layer was washed with brine, dried over sodium sulfate, filtered off and concentrated under reduced pressure providing crude 4-methyltetrahydro-2H-pyran-4-carbonitrile (1.8 g) as an orange oil, which was directly used in the next reaction without further purification. LCMS (m/z): 126.1 [M+H]+; Retention time = 0.44 min.

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

Reference£º
Patent; NOVARTIS AG; ANTONIOS-MCCREA, William R.; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; LIN, Xiaodong; MARTIN, Eric J.; PAN, Yue; PFISTER, Keith B; RENHOWE, Paul A.; SENDZIK, Martin; SUTTON, James; WAN, Lifeng; WO2012/101065; (2012); A2;,
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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

4-(Bromomethyl)tetrahydropyran (2.25 g; 12.55 mmol) is added to 2-oxo-2,3-dihydrobenzothiazole-6-sulfonic acid (4-ethylphenyl)isobutylamide (2.45 g; 6.27 mmol) and cesium carbonate (3.07 g; 9.41 mmol) dissolved in 1-methyl-2-pyrrolidone (50 ml). The reaction medium is stirred for 4 hours at 90 C., hydrolyzed and extracted with ethyl acetate. The organic phases are combined and then washed with brine, dried (Na2SO4) and concentrated. (0688) The crude product is chromatographed on silica gel (eluent: heptane/ethyl acetate, from 0 to 60% of ethyl acetate). The 3-oxo-4-(tetrahydropyran-4-ylmethyl)-3,4-dihydro-2H-benzo[1,4]thiazine-7-sulfonic acid (4-ethylphenyl)isobutylamide (2.19 g; 72%) is obtained in the form of a white crystalline solid. (0689) 1H NMR (DMSO-d6) delta: 0.85 (d, J=6.6 Hz, 7H), 1.13-1.22 (m, 4H), 1.24-1.55 (m, 6H), 2.03 (ddt, J=10.8, 6.9, 3.4 Hz, 1H), 2.50-2.66 (m, 3H), 3.23 (td, J=11.6, 2.1 Hz, 2H), 3.34 (s, 1H), 3.83 (ddd, J=11.3, 4.4, 1.9 Hz, 2H), 3.90 (d, J=7.3 Hz, 2H), 6.96-7.04 (m, 2H), 7.14-7.22 (m, 2H), 7.42 (dd, J=8.6, 1.9 Hz, 1H), 7.57 (s, 1H), 8.05 (d, J=1.9 Hz, 1H) (0690) MS: [M+H]=489, 125552-89-8

As the paragraph descriping shows that 125552-89-8 is playing an increasingly important role.

Reference£º
Patent; GALDERMA RESEARCH & DEVELOPMENT; MUSICKI, Branislav; BOUIX-PETER, Claire; OUVRY, Gilles; THOREAU, Etienne; (132 pag.)US2018/170869; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics