Heterocyclic Building Blocks-Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

234b) Ethyl 1 -(2,-fluoro-3′-((tetrahydro-2H-pyran-4-yl)oxy)-[1 ,1 ‘-biphenyl]-3-yl)-5-(2- (1 -methyl-1 H-1 ,2,3-triazol-4-yl)cyclopropyl)-1 H-pyrazole-4-carboxylate To a solution of ethyl 1 -(2′-fluoro-3’-hydroxy-[1 ,1 ‘-biphenyl]-3-yl)-5-(2-(1 -methyl-1 H-1 ,2,3- triazol-4-yl)cyclopropyl)-1 H-pyrazole-4-carboxylate (450 mg, 1 .006 mmol) in N,N- dimethylformamide (DMF) (5 mL) was added Cs2C03 (655 mg, 2.01 1 mmol) and 4- bromotetrahydro-2H-pyran (232 mg, 1 .408 mmol). It was heated in Microwave at 120 C for 2 h. The reaction mixture was diluted with water and extracted with ethyl acetate (2 x 30 mL). The combined organic layer was washed with chilled water (3 x 30 mL) and then brine solution (30 mL), dried over anhydrous Na2S04 and concentrated. The crude residue was purified by column chromatography eluting with 1 % methanol in DCM. Desired fractions were concentrated to give the title compound (200 mg, 0.217 mmol, 21 .58 % yield). LC-MS m/z 532.23 (M+H)+, 2.36 min (ret. time)., 25637-16-5

As the paragraph descriping shows that 25637-16-5 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; CALLAHAN, James Francis; KERNS, Jeffrey K.; LI, Peng; LI, Tindy; MCCLELAND, Brent W.; NIE, Hong; PERO, Joseph E.; DAVIES, Thomas Glanmor; GRAZIA CARR, Maria; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; NORTON, David; VERDONK, Marinus Leendert; WOOLFORD, Alison Jo-Anne; WILLEMS, Hendrika Maria Gerarda; (664 pag.)WO2017/60854; (2017); 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.

To a -10 C solution of tetrahydro-2H-pyran-4-ol (3.54 g, 34.66 mmol), triethylamine (4.65 g, 45.95 mmol) in DCM (100 mL) was added MsC1 (4.61 g, 40.24 mmol) dropwise. Afterstirring for 30 mm, the reaction mixture was diluted with water (100 mL), extracted with DCM (100 mL, 50 mL). The combined organic layers were washed with brine (1 x 50 mL), dried over anhydrous Na2504, filtered and concentrated under reduced pressure to give tetrahydro-2H-pyran-4-yl methanesulfonate (6.74 g). MS: m/z 181 (M+H) ., 2081-44-9

As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

Reference£º
Patent; JACOBIO PHARMACEUTICALS CO., LTD.; JACOBIO-ALPHA PHARMACEUTICALS CO., LTD.; MA, Cunbo; GAO, Panliang; HU, Shaojing; XU, Zilong; HAN, Huifeng; WU, Xinping; KANG, Di; LONG, Wei; (202 pag.)WO2018/172984; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

29943-42-8, Dihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a room temperature mixture of NaH (60% in hexane, 10.0 g, 250 mmol) in THF (300 mL) were added tetrahydropyran-4-one 1 (10.0 g, 100 mmol) and dimethylcarbonate (21 mL, 250 mmol). Then the mixture was heated to 45C overnight. The final mixture was poured into 0.0 IN HC1 and Et20, filtered over celite, the separated organic layer was dried over anhydrous sodium sulfate and the residue was purified over silica gel (petroleum ether/ethyl acetate =50: 1) to give the desired product 2 (7.8 g, 49% yield). 1H-NMR (300 MHz, CDCls) delta: 4.23 (m, 1H), 3.84 (t, 2H), 3.77 (m, 2H), 3.75 (s, 3H), 2.39 (m, 2H)., 29943-42-8

The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ZHOU, Han-Jie; PARLATI, Francesco; WUSTROW, David; WO2014/15291; (2014); 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.53911-68-5,4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

The solution of commercial 2,4-dichloro-6-nitroaniline (621 mg) and 3-(4- chlorophenyl)glutaric anhydride (674 mg) in 1,4-dioxane (2 ml) was heated to reflux shortly and stirred at rt for Ih. The solvent was removed by distillation and the residue dried in vacuo. The oily residue was dissolved in acetic acid (6 ml) and heated to reflux. Iron powder (1.01 g) was added and the mixture stirred under reflux for 1 h. Then cone. HCI (6 ml) was added cautiously and the green-yellow solution was refluxed for additional 2 h. All volatiles were removed at the water aspirator and the residue precipitated from acetic acid/cone. HCI solution with water. The solid was collected by suction filtration and washed well with IM HCI and water. The crude was recrystallised from acetic acid to give 4-(5,7-dichloro-2- benzimidazolyl)-3-(4-chlorophenyl)butanoic acid HCI (325 mg) as colourless crystals.1H-NMR (500 MHz, DMSOd5): delta (ppm) = 2.70 (dd, J = 16.2, 8.9 Hz, IH), 2.79 (dd, J = 16.2, 5.9 Hz, IH), 3.35 (dd, J = 14.7, 8.3 Hz, IH), 3.43 (dd, J = 14.7, 7.6 Hz, IH), 3.83 (m, IH), 7.33 (q, J = 8.6 Hz, 4H), 7.59 (d, J = 1.6 Hz, IH), 7.73 (d, J = 1.6 Hz, IH).13C-NMR and DEPT (125 MHz, DMSOd6) : delta (ppm) = 33.39 (CH2), 39.39 (CH), 39.46 (CH2), 112.58 (CH), 119.26 (C), 123.64 (CH), 128.28 (2 CH), 128.63 (C), 129.14 (2 CH), 131,1 (br, C), 131,29 (C), 134.40 (C), 141.22 (C), 154.96 (C), 172.24 (CO). MS ( + ESI): m/z = 383 (M + H)., 53911-68-5

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; ENGEL, Matthias; FROeHNER, Wolfgang; STROBA, Adriane; BIONDI, Ricardo M.; WO2010/43711; (2010); 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.101691-65-0,(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

To a solution of 224 g (0.83 mol) of Compound 7 in methyl isobutylketone (1.6 L) are added 189 g (1.66 mol) of potassium thioacetate. The beige suspension is stirred at 70 C. for 4.5 h. The reaction mixture is cooled to room temperature and water (1.8 L) is added. The organic layer is washed with 10% aqueous K2CO3 solution (1.8 L) and water (1 L). The organic layer is filtered through Celite (20 g), activated charcoal (20 g) and Na2SO4 (20 g) and the filtrate is concentrated under reduced pressure. The residual oil is azeotroped with methylcyclohexane (200 mL) and n-heptanes (250 mL) to afford 138 g of Compound 8 as a yellow-orange oil. Yield: 96%; ES-MS: m/z 175 [M+H]; 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.23-1.40 (2H, m), 1.59-1.78 (3H, m), 2.33 (3H, d, J=4.16 Hz), 2.82 (2H, dd, J=6.24, 3.79 Hz), 3.27-3.39 (2H, m), 3.88-4.02 (2H, m)., 101691-65-0

Big data shows that 101691-65-0 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/71196; (2011); 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

To a solution of 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy)-4-(3- ((2- (2-cyclopropylphenyl) pyrrolidin-1-yl) methyl) azetidin-1-yl) benzoic acid (40 mg, 0.08 mmol) in DCM (10 mL) was added HATU (36 mg, 0.09 mmol) and TEA (86 mg, 0.85 mmol), the solution was stirred for about 0.5h, 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzenesulfonamide (27 mg, 0.170 mmol) and DMAP (12 mg, 0.09 mmol) was then added, the solution was stirred at r.t for 16h. The reaction solution was concentrated and purified by column chromatograph on silica gel (100-200 mesh, eluent: MeOH/DCM = 1/10) to give the crude product, which was purified by Pre-TLC (MeOH/DCM = 1/18) to obtain the desired compound. 1H NMR (CDCl3) delta ppm: 10.12 (s, 1H), 9.14 (s, 1H), 8.89 (s, 1H), 8.57-8.46 (m, 1H), 8.24-8.09 (m, 2H), 7.90 (d, J = 8.8Hz, 1H), 7.69 (s, 1H), 7.55-7.37 (m, 2H), 7.16-7.03 (m, 2H), 6.97-6.82 (m, 2H), 6.55 (s, 1H), 6.01 (d, J = 8.4Hz, 1H), 5.37 (s, 1H), 4.10-3.98 (m, 2H), 3.84-3.71 (m, 2H), 3.49-3.14 (m, 7H), 2.80-2.51 (m, 2H), 2.39-2.11 (m, 3H), 2.04-1.67 (m, 7H), 1.50-1.35 (m, 3H), 0.93-0.81 (m, 2H), 0.73-0.46 (m, 2H). MS (ESI, m/e) [M+1] + 805.8.

1228779-96-1, As the paragraph descriping shows that 1228779-96-1 is playing an increasingly important role.

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

4677-20-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4677-20-7,4-(2-Bromoethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

Intermediate 28: 2-(ButyloxyV8-(methyloxyV9-(2-{r2-(tetrahvdro-2H-pyran-4- yl)ethylloxy)ethyl)-9H-purin-6-amineTo 2-[6-amino-2-(butyloxy)-8-(methyloxy)-9H-purin-9-yl]ethanol (0.03 g, 0.107 mmol) in dry THF (3ml) was added potassium f-butoxide solution in THF (0.160 ml, 0.160 mmol) followed by 4-(2-bromoethyl)tetrahydro-2H-pyran (0.031 g, 0.160 mmol) in THF 2ml) and the resulting white suspension was heated at 500C for 18 hours then at 7O0C for 7 hours. Additional 4-(2-bromoethyl)tetrahydro-2H-pyran, (0.031 g, 0.160 mmol) and potassium f-butoxide solution in THF (0.160 ml, 0.160 mmol) were added and the mixture heated at 7O0C for 72 hours. The mixture was cooled and quenched with water (5ml), extracted with DCM (2x5ml), the organic phase was isolated by separation through a hydrophobic frit and evaporated. The sample was dissolved in 1 :1 MeOH:DMSO (1 ml) and purified by Mass Directed AutoPrep. The solvent was dried under a stream of nitrogen to give the title compound as a colourless gum (3.1 mg). LCMS: tRET = 2.17 min; MH+ 394

The synthetic route of 4677-20-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; CAMPOS, Sebastien, Andre; COE, Diane, Mary; SMITH, Stephen, Allan; TRIVEDI, Naimisha; WO2010/18132; (2010); 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.19752-84-2,Tetrahydro-2H-pyran-3-ol,as a common compound, the synthetic route is as follows.

Combine tetrahydropyran-3-ol (1.3 g. 13 mmoi), 1-(methyisuifoni)-3-nitro-1H- pyrazole (2.4 g, 1.0 eq), and cesium carbonate (4.8 g, 1.2 eq) in acetonitrile (40 mL). Stir at 90 ?C overnight. Concentrate the mixture in vacuo. Dilute with EtOAc and filter through a pad of diatomaceous earth. Concentrate the filtrate in vacuo to provide a i-esidue. Subject the residue to C- 18 reverse phase chromatography eluting with a gradient from 0% to 100% of (0. 1% formic acid in acetonitrile) in (0. 1% formic acid in water), to give the title compound (0.35 g, 14%). MS (ES) m/z = 198 (M¡ÀH)., 19752-84-2

The synthetic route of 19752-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; BASTIAN, Jolie Anne; CLAYTON, Joshua Ryan; COATES, David Andrew; SALL, Daniel Jon; WOODS, Timothy Andrew; (58 pag.)WO2018/13486; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

130290-79-8, (Tetrahydro-2H-pyran-4-yl)methanamine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 500 mL three-neck RB flask equipped with a mechanical stirrer were charged the 4-chloro-3-nitrobenzenesulfonamide, Compound M (10.0 g), diisopropylethylamine (17.5 g), (tetrahydro-2H-pyran-4-yl)methanamine (7.0 g) and acetonitrile (150 mL). The reaction mixture was adjusted to an internal temperature of 80 C. and agitated for no less than 12 hours. The product solution was cooled down to 40 C. and agitated for no less than 1 hour until precipitation observed. The product slurry was further cooled to 20 C. Water (75 mL) was slowly charged over no less than 1 hour, and the mixture cooled to 10 C. and agitated for no less than 2 hours before collected by filtration. The wet cake was washed with 1:1 mix of acetonitrile:water (40 mL). The wet cake was then reslurried in water (80 mL) at 40 C. for no less than 1 hour before collected by filtration. The wet cake was rinsed with water (20 mL), and dried at 75 C. under vacuum to give 12.7 g of the desired product in 99.9% purity and in 91% weight-adjusted yield. 1H NMR (DMSO-d6): delta 1.25 (m, 2H), 1.60 (m, 2H), 1.89 (m, 1H), 3.25 (m, 2H), 3.33 (m, 2H), 3.83 (m, 2H), 7.27 (d, J=9.3 Hz, 1H), 7.32 (s, NH2, 2H), 7.81 (dd, J=9.1, 2.3 Hz, 1H), 8.45 (d, J=2.2 Hz, 1H), 8.54 (t, J=5.9 Hz, 1H, NH).

130290-79-8, As the paragraph descriping shows that 130290-79-8 is playing an increasingly important role.

Reference£º
Patent; ABBVIE INC.; Chan, Vincent S.; Christesen, Alan C.; Grieme, Timothy A.; Ku, Yi-Yin; Mulhern, Mathew M.; Pu, Yu-Ming M.; US2014/275540; (2014); 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.4677-20-7,4-(2-Bromoethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

Intermediate 17: 2-Butoxy-8-methoxy-9-r2-(tetrahvdro-2/-/-pyran-4-yl)ethyll-9/-/-purin- 6-amine2-Butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate salt (0.2 g) in anhydrous N, N- dimethylformamide (5 ml.) was treated with anhydrous potassium carbonate (0.315 g) and then heated to 600C for 1 hour. On cooling to room temperature, to the above was added 4-(2-bromoethyl)tetrahydro-2H-pyran (0.110 g) and the reaction was warmed to 500C, overnight. The reaction mixture was quenched with water (5 ml.) and extracted into ethyl acetate (3 times, 100 ml. combined total volume). The separated organic layers were combined and passed through a hydrophobic frit to dry. The organic phase was stripped to give a gum which was purified by C-ibeta reverse phase chromatography using water (containing 0.1 % formic acid)-acetonitrile (containing 0.05% formic acid) as eluant (20-60%) to afford the title compound as a white solid (11 1 mg). MS calcd for (Ci7H27N5Os)+ = 349 MS found (electrospray): (M+H)+ = 3501 H NMR (CDCI3): 5.20 (2H, s), 4.24 (2H, t), 4.10 (3H, s), 3.94 (4H, overlapping m), 3.31 (2H, m), 1.78-1.65 (6H, overlapping m), 1.52-1.39 (3H, overlapping m), 1.30 (2H, m), 0.95 (3H, t).

4677-20-7, 4677-20-7 4-(2-Bromoethyl)tetrahydropyran 22637012, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/101867; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics