Category: Tetrahydropyrans

1152567-60-6, 4-(4-Bromophenyl)tetrahydro-2H-pyran-4-carboxylic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of 4-[4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]-tetrahydro- pyran-4-carboxylic acid To a mixture of 1-20 (91 mg, 0.32 mmol), R-8 (95 mg, 0.38 mmol),bis(triphenylphosphine)palladium(II)dichloride (27 mg, 0.03 mmol) in THF (2.0 mL) at room temperature is added KC03 (128 mg, 1.3 mmol), and H20 (0.3 mL). The mixture is heated in the microwave at 120 C for 30 minutes, allowed to cool to roomtemperature, and concentrated in vacuo. The residue is purified by flash chromatography (Si02, 0-10% MeOH in CH2C12) to give the title intermediate 1-32 (83 mg).

1152567-60-6, The synthetic route of 1152567-60-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela; CHEN, Zhidong; DE LOMBAERT, Stephane; EMMANUEL, Michel Jose; LOKE, Pui Leng; MAN, Chuk Chui; MORWICK, Tina Marie; TAKAHASHI, Hidenori; WO2012/82817; (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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

Synthesis of 3-Methoxy-4-(tetrahydro-pyran-4-ylmethoxy)-benzonitrile (For Example1 .0 g 4-Hydroxy-3-methoxybenzonitrile, 1.1 g potassium carbonate and 2.0 g 4-(iodomethyl)- tetrahydropyran were placed in 20 mL acetone and heated to reflux overnight. After this time,1 .1 g potassium carbonate was added and the reaction was heated at reflux for a further 2 h before more 0.93 g potassium carbonate was introduced and reflux was continued for a further 3 h. The mixture was then cooled to ambient temperature and concentrated under reduced pressure. The material that remained was partitioned between diethyl ether and water and the aqueous phase was removed and extracted with additional diethyl ether. The combined organic fractions were dried, filtered and the filtrate was concentrated under reduced pressure. Purification by silica gel chromatography (Si02: ethyl acetate/heptanes: 10% to 30%) provided the title compound. Yield: 307 mg (19% of theory)Analysis: HPLC-MS (Method B): Rt: 1 .85 min., 101691-94-5

101691-94-5 4-(Iodomethyl)tetrahydro-2H-pyran 2795507, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; DAHMANN, Georg; FIEGEN, Dennis; HANDSCHUH, Sandra; KLICIC, Jasna; LINZ, Guenter; SCHAENZLE, Gerhard; SCHNAPP, Andreas; EAST, Stephen P.; MAZANETZ, Michael Philip; SCOTT, John; WALKER, Edward; WO2011/92128; (2011); 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.

solution of 3,5-difluorophenol (1.15 g, 8.81 mmol), tetrahydro-2H-pyran-3-ol (0.900 g, 8.81 mmol), triphenylphosphine (2.31 g, 8.81 mmol) and DIAD (1.74 mL, 8.81 mmol) in THF (10 mL) was stirred overnight. The solution was then concentrated under reduced pressure and the residue was purified by purified by column chromatography on silica gel using CombiFlash apparatus eluting with EtOAc/hexanes (0-30%). The purification afforded 1.43 g (75.8%) of the sub-title compound as a colorless oil., 19752-84-2

As the paragraph descriping shows that 19752-84-2 is playing an increasingly important role.

Reference£º
Patent; INCYTE CORPORATION; Xue, Chu-Biao; Li, Yun-Long; Geng, Hao; Pan, Jun; Wang, Anlai; Zhang, Ke; Yao, Wenqing; Zhang, Fenglei; Zhuo, Jincong; US2014/200227; (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.4295-99-2,4-Cyanotetrahydro-4H-pyran,as a common compound, the synthetic route is as follows.

In a 30 ml glass flask equipped with a stirrer, a thermometer and a dropping funnel, 1.0 g (9.0 mmol) of 4-cyanotetrahydropyran and 5 ml of dry tetrahydrofuran were added, and the liquid temperature was maintained at 0 to 5C.,10.8 ml (10.8 mmol) of a 1.0 mol/l lithium bis (trimethylsilyl)amide in tetrahydrofuran solution was gently added dropwise, and the mixture was stirred at the same temperature for 1.5 hours. Then, 3.8 g (27 mmol) of iodomethane was added, the mixture was reacted at room temperature for 2 hours. After completion of the reaction, 15 mmol (15 mmol) of 1.0 mmol / l hydrochloric acid was added to the obtained reaction solution, under ice cooling, the reaction solution was concentrated. To the concentrate, 10 ml of a saturated aqueous sodium chloride solution was added, extracted twice with 30 ml of ethyl acetate, the extract was dried over anhydrous magnesium sulfate. After filtration, the concentrate was distilled under reduced pressur to obtain 0.98 g of 4-methyl-4-cyanotetrahydropyran (isolation yield: 87%) as light yellow liquid., 4295-99-2

4295-99-2 4-Cyanotetrahydro-4H-pyran 11815837, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; UBE INDUSTRIES LIMITED; NISHINO, SHIGEYOSHI; HIROTSU, KENJI; SHIMA, HIDEYOSHI; IWAMOTO, KEIJI; HARADA, TAKASHI; (13 pag.)JP5673729; (2015); B2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

23462-75-1, Dihydro-2H-pyran-3(4H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

23462-75-1, Dihydro-2H-pyran-3(4H)-one (4.00 g, 40.0 mmol) was dissolved in THF (32.0 mL) and chlorotrimethylsilane (12.8 mL, 100 mmol) was added. The reaction was stirred at room temperature for 10 minutes. Triethylamine (15.0 mL, 108 mmol) was then added dropwise under nitrogen. A white precipitate formed and the resulting suspension was heated to 70C over the weekend. The reaction mixture was cooled to room temperature and concentrated in vacuo. Pentane (80 mL) was added, the suspension was filtered, and the solid was washed with pentane (40 mL). The filtrate was concentrated in vacuo to give the title compound as a liquid that was used as is in the next step without further purification. 1H NMR (500 MHz, CDCI3) delta 4.98-4.92 (m, 1H), 3.88 (m, 2H), 3.69 (t, / = 5.5 Hz, 2H), 2.16 (m, 2H), 0.19 (s, 9H).

As the paragraph descriping shows that 23462-75-1 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; MARTINEZ, Michelle; FALCONE, Danielle; TORRES, Luis; DENG, Yongqi; KURUKLASURIYA, Ravi; ZENG, Hongbo; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146491; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

220641-87-2, N-Methyltetrahydro-2H-pyran-4-amine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step C:; A 25 mL round bottom flask were charged with 86-3 (0.022 g, 0.038 mmol), methylene chloride (2 mL), N-methyl-N-tetrahydro-2H-pyran-4-ylamine (0.009 g, 0.56 mmol), sodium triacetoxyborohydride (0.032 g, 0.15 mmol), molecular sieves (20 mg) and triethyl amine (0.019 g, 0.188 mmol). The mixture was stirred at room temperature for 12 hours. The reaction mixture was quenched with MeOH and stirred for 20 minutes, then filtered and concentrated. The resulting residue was purified by RP HPLC (YMC column, 20% to 80% acetonitrile in water) to afford product 86-4 as a TFA salt (m/z (ES) (M+H)+= 683)., 220641-87-2

The synthetic route of 220641-87-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK & CO., INC.; WO2007/41052; (2007); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

101691-65-0, (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,101691-65-0

Step 3: Synthesis of Thioacetic acid S-(tetrahydro-pyran-4-ylmethyl)ester; Prepared as described by adaptation of the following literature reference:Watson, R. J. et al. Tetrahedron Lett. 2002, 43, 683-685.To a solution of 224 g (0.83 mol) of toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester 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 thioacetic acid S-(tetrahydro-pyran-4-ylmethyl)ester as a yellow-orange oil (CAUTION: Stench.). 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)

The synthetic route of 101691-65-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Boehringer Ingelheim International GmbH; US2010/76029; (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.53911-68-5,4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.,53911-68-5

The solution of commercial 3,4-diaminobenzophenone (0.43 g) and 3-(4- chlorophenyl)glutaric anhydride (0.45 g) in 1,4-dioxane (3 ml) was stirred under reflux for 0.5 h. 4M HCI in 1,4-dioxane (3 ml) was added and the solution is further heated to reflux for 2.5 h. After cooling to rt the precipitate is collected by suction filtration and washed with 1,4-dioxane and diethyl ether. The crude is recrystallised from acetic acid to give 4-(5-benzoyl-2-benzimidazolyl)-3-(4-chlorophenyl)butanoic acid HCI (0.64 g) as light brown solid.1H-NMR (500 MHz, DMSOd5)): delta (ppm) = 2.74 (dd, J = 16.2, 8.6 Hz, IH), 2.85 (dd, J = 16.2, 6.1 Hz, IH), 3.50 (dd, J = 15.0, 9.1 Hz, IH), 3.60 (dd, J = 15.0, 6.9 Hz, IH), 3.91 (m, IH), 7.32 (d, J = 8.5 Hz, 2H), 7.39 (d, J = 8.5 Hz, 2H), 7.58 (t, J = 7.6 Hz, 2H), 7.70 (t, J = 7.4 Hz, IH), 7.75 (dd, J = 8.3, 1.3 Hz, 2H), 7.83 (dd, J = 8.6, 1.5 Hz, IH), 7.86 (d, J = 8.6 Hz, IH), 8.01 (d, J = 1.4 Hz, IH). 13C-NMR and DEPT (125 MHz, DMSOd6) : delta (ppm) = 32.83 (CH2), 39.17 (CH), 39.67 (CH2), 113.91 (CH), 115.78 (CH), 126.51 (CH), 128.37 (2 CH), 128.52 (2 CH), 129.19 (2 CH), 129.54 (2 CH), 131.02 (C), 131.46 (C), 132.70 (CH), 133.79 (C), 133.95 (C), 136.90 (C), 140.75 (C), 154.47 (C), 172.14 (CO), 194.71 (CO).

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.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

To a suspension of magnesium (24.3 g, 1.00 mol) in THF (500 mL) under N2 was added three iodine crystals,Then, dropwise pure 4-bromotetrahydro-2H-pyran (100g, 607mmoL),During the dropwise addition, the internal temperature is controlled to be lower than 45 C.The reaction mixture was stirred for a further 2 h at ambient temperature.The reaction mixture was cooled to -30 C, and then a solution of 3-fluoropyridaldehyde (50.3 g, 402 mmoL) in THF (300 mL) was added dropwise, and the internal temperature was maintained at -20 C to -30 C during the dropwise addition.After 1 h, the reaction mixture was filtered through a thin pad of diatomaceous earth.To the filtrate was added a saturated aqueous solution of NH4Cl (100 mL), and the layers were separated.The organic phase was dried over anhydrous Na2SO4 and the filtrate was collected. The filtrate was concentrated on a rotary evaporator.The crude compound was purified using reversed-phase chromatography, eluting with 40-50% MeCN in H2O, to obtain a racemic compound (52 g, 61% yield),It was separated by chiral preparation SFC to obtain enantiomer A (25.1 g, 29.6% yield)And enantiomer B (25.3 g, 29.7% yield)., 25637-16-5

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

Reference£º
Patent; Beijing Jiakesitu Drug Discovery Co., Ltd.; Beijing Jiakesi Drug Discovery Co., Ltd.; Fang Haiquan; Li Haijun; Yang Guiqun; Wang Yanping; Wu Lingjun; Li Qinglong; Du Yuelei; Zhang Lei; Hu Shaojing; (65 pag.)CN110407854; (2019); 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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

V-tert-Butyl-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-({[2-(4-chloro-2-hydroxyphenyl) ethyl]sulfonyl}amino)benzenesulfonamide (4.05 g, 5.67 mmol) devided in three vials (1.35 g, 1.89 mmol in each vial), cesium carbonate (2.77 g, 8.49 mmol in each vial), 4- bromomethyltetrahydropyran (1.52 g, 8.49 mmol in each vial) and Lambda/,/V-dimethylformamide (12 mL in each vial) were mixed and heated in a MW at 110 C for 1 h. The reaction mixtures were filtered and the solvent was evaporated. The combined crude product was mixed with water/ethyl acetate and the aqueous phase was extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and the solvent was evaporated. Purification by chromatography on silica using gradient elution 5- 50 % EtOAc in heptane gave 3.23 g (70 % yield) of the title compound. XH NMR (500 MHz, DMSO-de) delta ppm 1.04 (s, 9 H) 1.08 (s, 9 H) 1.11 (s, 1 H) 1.18 – 1.28 (m, 2 H) 1.52 – 1.58 (m, 2 H) 1.83 – 1.91 (m, 1 H) 2.94 – 2.99 (m, 2 H) 3.20 – 3.27 (m, 2 H) 3.44 – 3.49 (m, 2 H) 3.79 (m, 3 H) 4.79 (s, 2 H) 6.91 (dd, 1 H) 7.01 (d, 1 H) 7.18 (d, 1 H) 7.40 – 7.45 (m, 4 H) 7.46 (d, 2 H) 7.52 (dd, 1 H) 7.61 – 7.65 (m, 5 H) 7.99 (s, 1 H) 8.03 (d, 1 H) 8.73 (s, 1 H). MS (ES ) m/z 811,813 [M-H]”., 125552-89-8

The synthetic route of 125552-89-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ACTURUM LIFE SCIENCE AB; SOeDERMAN, Peter; SVENSSON, Mats A; KERS, Annika; OeHBERG, Liselott; HOeGDIN, Katharina; HETTMAN, Andreas; HALLBERG, Jesper; EK, Maria; BYLUND, Johan; NORD, Johan; (0 pag.)WO2016/85392; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics