Category: Tetrahydropyrans

101691-94-5, 4-(Iodomethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Example 40 tert-butyl 4-{2-[methoxy(methyl)amino]-2-oxo-1-(tetrahydro-2H-pyran-4-ylmethyl)ethyl}benzoate [Show Image] Lithium diisopropylamide (2M tetrahydrofuran solution, 6.9 mL) was diluted with tetrahydrofuran (20 mL), a solution of tert-butyl 4-{2-[methoxy(methyl)amino]-2-oxoethyl}benzoate (3.70 g) in a mixed solvent of tetrahydrofuran (20 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (12 mL) were added at -78C, and the mixture was stirred for 1 hr. To the reaction mixture was added a solution of 4-(iodomethyl)tetrahydro-2H-pyran (3.30 g) in tetrahydrofuran (20 mL) at -78C and the mixture was stirred for 3 hr. The mixture was slowly warmed to room temperature, and stirred overnight. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (3.81 g, yield 76%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS:378(MH+).

The synthetic route of 101691-94-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP2149550; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

Thionyl chloride (0.17 mL, 2.4 mmol) was added to a stirred solution of tetrahydro-pyran-3- carboxylic acid (0.26 g, 2.0 mmol) in DCM (4 mL) and DMF (0.1 mL). The mixture was stirred at room temperature for 30 min then Meldrum’s acid (0.576 g, 4.0 mmol) was added and the mixture was left to stir at room temperature for 1 hour. The reaction mixture was washed with a 2 N HC1 (aq) solution and evaporated under reduced pressure. The residue was dissolved in methanol and heated to reflux for 6 h. The mixture was then concentrated under reduced pressure to give the title compound (0.27 g, 75percent yield) which was used in the next step without further purification.

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Reference£º
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; CARSWELL, Emma, L.; CHARLES, Mark, David; COCHI, Anne; DUGAN, Benjamin, J.; EKWURU, Chukuemeka, Tennyson; ELUSTONDO, Fred; FOWLER, Katherine, M.; LEROUX, Frederic, Georges, Marie; MONCK, Nathaniel, J.T.; OTT, Gregory, R.; ROFFEY, Jonathan, R.; SIDHU, Gurwinder; TREMAYNE, Neil; (305 pag.)WO2018/55402; (2018); A1;,
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

Step 2 [0340] (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate obtained in Step 1 (1.20 g, 4.44 mmol) was dissolved in acetone (15 mL), sodium iodide (2.00 g, 13.3 mmol) was added thereto, and under reflux with heating, the mixture was stirred for 4 hours. After cooling the reaction mixture to room temperature, the precipitated solid was removed by filtration, and the filtrate was evaporated under reduced pressure. Chloroform was added to the residue, and the precipitated solid was removed by filtration. The filtrate was concentrated under reduced pressure, whereby 4-(iodomethyl)tetrahydro-2H-pyran (0.946 g, 94%) was obtained. 1H NMR (300 MHz, CDCl3, delta): 3.99-3.96 (m, 2H), 3.37 (td, J = 11.7, 2.1 Hz, 2H), 3.10 (d, J = 6.6 Hz, 2H), 1.81-1.65 (m, 3H), 1.37-1.24 (m, 2H).

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Reference£º
Patent; Kyowa Hakko Kirin Co., Ltd.; FURUTA, Takayuki; SAWADA, Takashi; DANJO, Tomohiro; NAKAJIMA, Takahiro; UESAKA, Noriaki; EP2881394; (2015); 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

The mixture of 3- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy) -4′- ((2-phenylpyrrolidin-1-yl) methyl) – [1, 1′-biphenyl] -4-carboxylic acid (170 mg, 0.35 mmol), triethylamine (106 mg, 1.05 mmol), 2- (7-azabenzotriazol-1-yl) -N, N, N’, N’-tetramethyluronium hexafluorophosphate (201 mg, 0.53 mmol) in DCM (10 mL) was stirred for 2 hours at room temperature. To the resulted reaction mixture were added 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzenesulfonamide (167 mg, 0.53 mmol) and DMAP (5 mg, 0.04 mmol) and then stirred overnight. The reaction mixture was extracted with DCM (30 mL) and water (30 mL). The organic layer was concentrated in vacuo and purified by chromatography column on silica (eluent: DCM/MeOH = 20/1 to 10/1) to afford a crude product, which was then purified with Pre-HPLC to give the product (14.28 mg). 1H NMR (400 MHz, DMSO-d 6) delta ppm: 12.41 (br, 1H), 11.67 (br, 1H), 8.51 (br, 2H), 8.04 (m, 1H), 7.79 (d, J = 8.0 Hz, 1H), 7.62 (d, J = 8.0 Hz, 1H), 7.42-7.27 (m, 12H), 6.99 (m, 2H), 6.37 (m, 1H), 3.85 (d, J = 8.0 Hz, 2H), 3.67 (m, 1H), 3.28-3.23 (m, 6H), 3.10-2.96 (m, 2H), 2.15 (m, 2H), 2.01 (m, 1H), 1.87 (m, 2H), 1.61 (d, J = 8.0Hz, 2H), 1.45 (m, 2H). MS (ESI, m/e) [M+1] + 787.2.

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

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.

Into a 8- mL round-bottom flask, was placed 4-(4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-l-en-l- yl]methyl]piperazin-l-yl)-2-[l4-thia-2,4,l0-triazatricyclo[7.5.0.0A[3,7]]tetradeca-l(9),2,5,7- tetraen-lO-yl]benzoic acid (30 mg, 0.05 mmol, 1 equiv), 3-nitro-4-[[(oxan-4- yl)methyl]amino]benzene-l-sulfonamide (17 mg, 0.06 mmol, 1.20 equiv), EDCI (18 mg, 0.09 mmol, 2 equiv), DMAP (23 mg, 0.19 mmol, 4 equiv), DCM (3 mL). The resulting solution was stirred for overnight at room temperature. The resulting mixture was concentrated. The crude product was purified by Flash-Prep-HPLC with the following conditions (IntelFlash-l): Column, C18 silica gel; mobile phase, Water(0. l%FA) and ACN (48.0% ACN up to 53.0% in 7 min, hold 95.0% in 1 min, down to 48.0% in 1 min within 5 ; Detector, UV 254 nm. This resulted in 10.6 mg (24.15%) of 4-(4-[[2-(4-chlorophenyl)-4,4- dimethylcyclohex- l-en- l-yl]methyl]piperazin- l-yl)-N-(3-nitro-4-[[(oxan-4- yl)methyl]amino]benzenesulfonyl)-2-[l4-thia-2,4,l0-triazatricyclo[7.5.0.0A[3,7]]tetradeca- l(9),2,5,7-tetraen-l0-yl]benzamide as a yellow solid. LC-MS: (ES, m/z ): M+l=939, R,T= 3.55 min. The measurements of the retention were done with a reversed phase column (C18). Shimadzu LCMS 2020; 50*3.0 Kinetex 2.6u XB-C18 , 2.6 microm; Eluent A: water (0.05 % TFA); Eluent B: Acetonitrile; linear gradient. H-NMR: (CDC13, 300 ppm): 8.7l(s, 1H), 8.49 (s, 1H), 7.99-7.97(m, 1H), 7.8l-7.77(m, 1H), 7.38-7.28(m, 4H), 7.0l-6.93(m, 2H), 6.88- 6.72(m, 3H), 3.36(s, 1H), 4.06-3.26(m, 18H), 2.73-2.22(m, 6H), 2. l3-l.73(m, 3H), 1.79- l.25(m, 6H), l.00(s, 6H).

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

Reference£º
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (475 pag.)WO2020/41406; (2020); 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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

Step 7: Preparation for tetrahydro-2H-pyran-4-ol (0177) To a solution of lithium aluminium hydride (0.95 g, 25 mmol) in tetrahydrofuran (40 mL) was dihydro-2H-pyran-4(3H)-one (2.0 g, 20 mmol) with stirring at 0 C. The mixture was stirred at ambient temperature for 2 hours, quenched with sodium hydroxide (30%, 0.45 g), filtered, dried over magnesium sulfate, filtered and concentrated to obtain a crude product as a light-yellow oil (2.0 g, yield=95%).

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

Reference£º
Patent; BEIJING SCITECH-MQ PHARMACEUTICALS LIMITED; SHENG, Wang; YANG, Leifu; PAN, Zhiyong; (46 pag.)US2017/355683; (2017); 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

Step. Preparation of dideutero-(tetrahydro-2H-pyran-4-yl)methanamine: To a solution of tetrahydro-2H-pyran-4-carbonitrile (800 mg, 7.20 mmol) in THF (20 ml_) was added aluminum(lll) lithium deuteride at 0 C. The mixture was stirred at 0 C for 2 hr. To the stirred reaction mixture was sequentially added 300 uL of water, 900 muIota_ of 1 N NaOH and 300 muIota_ of water. The mixture was filtered through a thin layer of celite to remove the solid. The filtrate was dried over sodium sulfate, filtered off and concentrated in vacuo giving 700 mg of titled compound. LCMS (m/z): 1 18.2 [M+H]+, retention time = 0.25 min. The crude product was used directly for next step.

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

Reference£º
Patent; NOVARTIS AG; ANTONIOS-MCCREA, William R.; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; MARTIN, Eric J.; PAN, Yue; LIN, Xiaodong; PFISTER, Keith B.; RENHOWE, Paul A.; SENDZIK, Martin; SUTTON, James; WAN, Lifeng; WO2012/101062; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics