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

To a solution of 1-bromo-4-(ethylsulfonyl)benzene (1.50 g) in 1,4-dioxane (20 mL) were added diethyl malonate (1.16 g), potassium phosphate (3.84 g), biphenyl-2-yl(di-tert-butyl)phosphine (108 mg) and palladium acetate (II) (40 mg). The reaction solution was purged with argon, and the mixture was heated under reflux for 12 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane = 10:90 – 50:50, volume ratio) to give a colorless oil. A solution of the obtained oil in N,N-dimethylformamide (20 mL) was purged with nitrogen, sodium hydride (60%, oil, 213 mg) was added under ice-cooling, and the mixture was stirred at 0C for 15 min. To the reaction solution was added a solution of 4-(iodomethyl)tetrahydro-2H-pyran (1.15 g) in N,N-dimethylformamide (10 mL) at 0C, and the mixture was stirred for 3 hr at 90C. The reaction mixture was concentrated under reduced pressure, saturated aqueous ammonium chloride solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane = 10:90 – 40:60, volume ratio) to give a colorless oil. To a solution of the obtained oil in a mixed solvent of tetrahydrofuran (40 mL) and methanol (20 mL) was added 2M aqueous sodium hydroxide solution (10 mL), and the mixture was stirred at 60C for 3 hr. The reaction solution was cooled to room temperature, and acidified with 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give the title compound (1.33 g, yield 67%) as colorless crystals. MS:327(MH+). Reference Example 67 4-[4-(ethylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one, 101691-94-5

As the paragraph descriping shows that 101691-94-5 is playing an increasingly important role.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP2149550; (2010); A1;,
Tetrahydropyran – Wikipedia
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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 IN 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, The synthetic route of 4295-99-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; ANTONIOS-MCCREA, William R.; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; MARTIN, Eric J.; PAN, Yue; PFISTER, Keith B.; SENDZIK, Martin; SUTTON, James; WAN, Lifeng; WO2012/66065; (2012); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.

To a vigorously stirred suspension of Mg (1.76 g, 72.8 mmol) turnings and iodine (46.1 mg, 0.182 mmol) in THF (2 mL) under N2 was added 1,2-dibromoethane (68.3 mg, 0.364 mmol) and 10% of a solution of 4-chlorotetrahydro-2H-pyran (4.4 g, 36.4 mmol) in THF (18 mL). Themixture was heated to 60C and as the reaction mixture turned clear and Grignard initiatedtook place, the remainder of the solution of 4-chlorotetrahydro-2H-pyran in THF was added slowly over 30 mm. The reaction mixture was stirred at 65C for 2h to give a solution of (tetrahydro2H-pyran-4-yl)magnesium chloride in THF (-2M). The Grignard solution was used without any further purification. The solution of 36-4 (800 mg, 2.06 mmol) in THF (150 mL) under N2 wasadded to Grignard reagent at 15C in one portion. After stirring at 15C for 2 mm, the mixture was quenched by 200 mL of sat.NH4C1 and extracted with 200 mL of EtOAc. The separated organic phase was washed with 200 mL of brine, dried over Na2504, filtered and concentrated. The residue was purified by Combi-flash (0%-30% of EtOAc in PE/DCM(v/v=1/1)) to afford 36-5 (550 mg, 56%) as off-white solid, and 50 mg of 36-5 was delivered. ?H NMR (400 MHz,CDC13) 5.32-5.25 (m, 1H), 4.06-3.96 (m, 2H), 3.42-3.29 (m, 3H), 2.39-2.33 (m, 1H), 2.07-1.79(m, 6H), 1.77-1.60 (m, 7H), 1.5 1-1.38 (m, 1OH), 1.35-1.21 (m, 4H), 1.16-1.01 (m, 8H), 0.97-0.90(m, 4H), 0.85 (t, J = 7.4 Hz, 3H), 0.71-0.66 (m, 3H). LCMS Rt = 1.212 mm in 2 mmchromatography, 30-9OAB_2MIN_E.M, MS ESI calcd. for C31H5102 [M+H-H2Oj 455, found455., 1768-64-5

As the paragraph descriping shows that 1768-64-5 is playing an increasingly important role.

Reference£º
Patent; SAGE THERAPEUTICS, INC.; SALITURO, Francesco, G.; ROBICHAUD, Albert, Jean; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd, L.; (157 pag.)WO2017/7840; (2017); A1;,
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4677-18-3,4677-18-3, 2-(Tetrahydro-2H-pyran-4-yl)ethanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: DIPEA (9.42mmol) was added to a solution of N-(tert-butoxycarbonyl)-1-methyl-d-tryptophan (3.14mmol), the appropriate alcohol or amine (3.14mmol) and HATU (3.14mmol) in acetonitrile (30mL) at 0C, and the solution was allowed to warm to rt. After stirring overnight (17h), the reaction was diluted with water (50mL) and the product was extracted with CH2Cl2 (3¡Á50mL). The combined organic extract was washed with water (25mL), brine (25mL) dried over Na2SO4 and concentrated under reduced pressure to afford the crude. Chromatographic purification afforded the desired product.

The synthetic route of 4677-18-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Adams, James; Brincks, Erik L.; Jaipuri, Firoz A.; Kumar, Sanjeev; Link, Charles; Marcinowicz, Agnieszka; Mautino, Mario R.; Potturi, Hima; Vahanian, Nicholas; Van Allen, Clarissa; Waldo, Jesse P.; Zhuang, Hong; European Journal of Medicinal Chemistry; vol. 198; (2020);,
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185815-59-2, 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 4(5)-3-(2-(Cinnamyloxy)-2-oxoethyl)-5-methylhexanoic acid (III) – (opposite enantiomer to Example 3)Quinidine (17.2g, 52.8mmol) was suspended in toluene (23OmL). Cinnamyl alcohol (9.3 g, 69mmol) was added and the reaction mixture was cooled to -35 0C. The solution of 3- isobutylglutaric anhydride (9.Og, 52.8mmol) in toluene (6mL) was added during 15 min and the reaction mixture was stirred at -38 C for 24 hours. Working up is carried out analogously to the preparation of the compound from Example 3. Combined extracts were warmed to 35 0C and (S)- alpha-phenylethylamine (5.8 g, 48mmol) was added, followed by seed crystals (10 mg). The mixture was stirred for 4 hours at 25C and filtered to obtain 14.6 g of (5)-alpha-phenylethylamine salt of (S)- 3-(2-(cinnamyloxy)-2-oxoethyl)-5-methylhexanoic acid. Salt was suspended in toluene (90 mL) and stirred with 3% HCl (600 mL) until clear solution was obtained. Aqueous acidic solution was separated and organic layer was washed once again with 3% HCl (2OmL). Evaporation of toluene afforded 10.2 g (65%) of monoester as viscous yellowish oil. HPLC analysis on Chiralpak AS column, hexane/EtOH/TFA=95/5/0.1 revealed 91.4 % ee.1H NMR (CDCl3), delta/ppm: 0.87 (d, 6H, J=6.5 Hz), 1.21-1.27 (m, 2H), 1.56-1.70 (m, IH), 2.38-2.48 (m, 5H), 4.73 (dd, 2H, Jy=6.5 Hz, J2=1.2 Hz), 6.27 (dt, IH J/=15.8 Hz, J2=6.5 Hz), 6.65 (d, IH, J=15.8 HZ), 7.22-7.40 (m, 2H).13C NMR (CDCl3), delta/ppm: 22.34, 25.07, 29.64, 38.30, 38.48, 43.26, 64.92, 122.95, 126.50, 127.96, 128.49, 134.18, 136.07, 172.26, 178.64., 185815-59-2

185815-59-2 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione 11480690, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; PLIVA ISTRAZIVANJE I RAZVOJ D.O.O.; MCLEISH, Nicholas, Alistair, Maxwell; WO2008/9897; (2008); A1;,
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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

Prepared as described by adaptation of the following literature reference: Watson, R.J. et al. Tetrahedron Lett. 2002, 43, 683-685. To 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 suspension is stirred at 70 C for 4.5 h. The reaction mixture is cooled to RT and water (1 .8 L) is added. The organic layer is washed with 10% aq. K2C03 solution (1.8 L) and water (1 L). The organic layer is filtered through Celite (20 g), activated charcoal (20 g) and Na2S04 (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. Yield: 96%; ESI-MS: 175 [M+H]+

101691-65-0, 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; RIETHER, Doris; BINDER, Florian; DOODS, Henri; MUELLER, Stephan, Georg; NICHOLSON, Janet, Rachel; SAUER, Achim; WO2014/184327; (2014); A1;,
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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.

Intermediate 4Tetrahydro~2H-pyran-4-carbonitrile. A solution of tetrahydro-4Hr-pyran-4- one (25 g, 250 mmol) and toluenesulfonylmethyl cyanide (53.7 g, 275 mmol) dissolved in ethylene glycol dimethylether (1 L) was cooled to 0 C. Added dropwise over 30 min was a solution of potassium t-butoxide (56 g, 500 mmol) dissolved in t-butanol (350 mL) and ethylene glycol dimethylether (150 mL). After stirring the resulting mixture for 3 h at room temp, diethyl ether (1 L) was added and the organic phase was washed with saturated aqueous NaHCO3. The organic phase was dried (Na2SO4) and concentrated. The residue was distilled at 39 C 1.7 mm Hg to give the title compound as a colorless oil (10.87 g, 39% yield). 1H NMR (300 MHz, CDCl3) delta: 3.91-3.83 (2H, m), 3.61-3.54 (2H, m), 2.89-2.80 (IH, m), 1.97-1.78 (4H, m)., 29943-42-8

As the paragraph descriping shows that 29943-42-8 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/58646; (2007); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

2081-44-9, Tetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: Methanesulfonic acid tetrahydro-pyran-4-yl esterTo a solution of tetrahydro-2H-pyran-4-ol (25 g, 245 mmol) and triethyl amine (40.1 ml, 294 mmol) in CH2C12 (500 ml) at 0C was added dropwise methanesulfonylchloride (20.7 ml, 269 mmol) over a period of 40 mm, keeping the temperature between 0 – 4C. The reaction mixture was then allowed to stir at 0C for lhr. The cooling bath was removed and the mixture was stirred for another 90 mins at 25C. The mixture was washed with water (2 x 125m1), dried over anhydrous Na2504, filtered and concentrated under vacuum to get methanesulfonic acid tetrahydro-pyran-4-yl ester (38 g, 86%; crude) as liquid that was used in the next step without any further purification.

2081-44-9, The synthetic route of 2081-44-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GROEBKE ZBINDEN, Katrin; PINARD, Emmanuel; RYCKMANS, Thomas; WO2015/110370; (2015); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

4677-20-7, 4-(2-Bromoethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 51 can be prepared according to method 14 with modifications known to one of ordinary skill in the art. The last step of the preparation is provided: A mixture of 4-(2- bromoethyl)tetrahydro-2H-pyran (12.54 mg, 0.065 mmol), (E)-l-(4-(5-carbamoyl-2-(l-ethyl-3- methyl-lH-pyrazole-5-carboxamido)-lH-benzo[d]imidazol-l-yl)but-2-en-l-yl)-2-(l-ethyl-3- methyl-lH-pyrazole-5-carboxamido)-7-hydroxy-lH-benzo[d]imidazole-5-arboxamide (45 mg, 0.065 mmol) and potassium carbonate (22.44 mg, 0.162 mmol) was heated for 3hr at 85 C in DMSO (650 muIota) and NMP (650 muIota), then cooled. The residue was purified via acidic reverse phase chromatography (5% to 50% in 0.1% TFA in MeCN to 0.1% TFA in water; 50x30mm Phenomenex Eclipse, 5muMu C18 column, 20 min gradient). The pure fractions were partitioned between EtOAc and aqueous saturated sodium bicarbonate, the organic layer was separated, dried over sodium sulfate and evaporated in vacuoXa provide the title compound (8mg, 15.3% yield) as a white solid. *H NMR (DMSO-cfe, 600MHz): delta (ppm) 12.83 (br s, 2 H), 7.97-8.00 (m, 1 H), 7.93 (br s, 2 H), 7.69 (dd, 7=8.4, 1.5 Hz, 1 H), 7.63 (s, 1 H), 7.41 (d, 7=8.3 Hz, 1 H), 7.33 (br d, 7=11.4 Hz, 2 H), 7.29 (s, 1 H), 6.55 (s, 1 H), 6.52 (s, 1 H), 5.96-6.02 (m, 1 H), (2225) 5.70-5.79 (m, 1 H), 4.93 (br d, 7=5.0 Hz, 2 H), 4.82 (br d, 7=5.3 Hz, 2 H), 4.49-4.58 (m, 4 H), 3.96 (br t, 7=6.7 Hz, 2 H), 3.75 (br dd, 7=11.2, 2.9 Hz, 2 H), 3.16-3.23 (m, 2 H), 2.12 (d, 7=12.7 Hz, 6 H), 1.50-1.53 (m, 1 H), 1.45-1.49 (m, 2 H), 1.43 (br d, 7=11.9 Hz, 2 H), 1.28 (m, 6 H), 1.08 (br dd, 7=12.0, 3.6 Hz, 2 H); LCMS (LCMS Method K): Rt = 0.90 min, [M+H]+ = 805.5.

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

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CHARNLEY, Adam Kenneth; DARCY, Michael G.; DODSON, Jason W.; DONG, Xiaoyang; HUGHES, Terry V.; KANG, Jianxing; LEISTER, Lara Kathryn; LIAN, Yiqian; LI, Yue; MEHLMANN, John F.; NEVINS, Neysa; RAMANJULU, Joshi M.; ROMANO, Joseph J.; WANG, Gren Z.; YE, Guosen; ZHANG, Daohua; (451 pag.)WO2017/175147; (2017); A1;,
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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

Combine selenium dioxide (181.80 g, 1.64 mol), 1,4-dioxane (630 mL), acetic acid (31.5 mL, 0.67 eq), and water (31.5 mL). Heat to 90 C and add 1-(tetrahydro-pyran-4-yl)-ethanone (105.0 g, 1.0 eq) dropwise. Stir at 90 C overnight. After cooling, filter through a plug of silica/Celite and wash with tetrahydrofuran (2.5 L). Dry the organics over anhydrous magnesium sulfate, filter, and concentrate in vacuo. Dissolve the crude material in methanol (500 mL) and add to a solution of tert-butyl 4-formylpiperidine-1-carboxylate (174.72 g, 1.0 eq) and ammonium acetate (315.74 g, 5.0 eq) in methanol (1.45 L) at 0 C. Stir overnight. Filter through silica/Celite and wash with ethyl acetate and methanol. Concentrate the filtrate in vacuo. Dilute with methyl tert-butyl ether (400 mL) and water (400 mL), then adjust the pH to 2 by addition of aqueous 85% phosphoric acid. Separate the layers and wash the aqueous phase with methyl tert-butyl ether (200 mL). Basify the resulting aqueous phase with solid sodium carbonate to pH 10 and extract with ethyl acetate (3 x 200 mL). Wash the organics with saturated aqueous sodium chloride. Dry the organics over anhydrous magnesium sulfate, filter, and concentrate in vacuo to afford title compound 19c, tert-butyl 4-(4-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-2-yl)piperidine-1-carboxylate (105.1 g, 38%). MS (ES) m/z = 336 [M]+, 1H NMR (300.16 MHz, CDCl3): 6.63 (s, 1H), 4.26-4.11 (m, 2H), 4.07-4.00 (m, 2H), 3.51 (td, J=11.7, 1.8 Hz, 2H), 2.95-2.73 (m, 2H), 2.05-1.87 (m, 3H), 1.79-1.61 (m, 3H), 1.61-1.51 (m, 4H), 1.46 (s, 9H).

137052-08-5, As the paragraph descriping shows that 137052-08-5 is playing an increasingly important role.

Reference£º
Article; Parthasarathy, Saravanan; Henry, Kenneth; Pei, Huaxing; Clayton, Josh; Rempala, Mark; Johns, Deidre; De Frutos, Oscar; Garcia, Pablo; Mateos, Carlos; Pleite, Sehila; Wang, Yong; Stout, Stephanie; Condon, Bradley; Ashok, Sheela; Lu, Zhohai; Ehlhardt, William; Raub, Tom; Lai, Mei; Geeganage, Sandaruwan; Burkholder, Timothy P.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 10; (2018); p. 1887 – 1891;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics