Heterocyclic Building Blocks-Tetrahydropyrans

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a 2 L round bottomed flask, 2,2-dimethyldihydro-2H-pyran-4(3H)-one (10.4 g, 0.08 mol) was dissolved in water (500 mL) along with sodium metabisulfite (7.7 g, 0.04mol). The mixture was allowed to stir at rt for 1.5 h, then benzylpiperazine (14.2 g,0.08 mol) was added. The mixture was stirred for 2 h and potassium cyanide (8.42 g,0.13 mol) was added to the reaction mixture. After stirring at rt for 2 days the solidformed was filtered and dried, to give the title compound as a white solid (15.4 g, yield61%). HPLC-MS (Method A): Ret, 1.98 mm; ESl-MS m/z, 314.1 (M+1)., 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; LABORATORIOS DEL DR. ESTEVE, S.A.; GARCIA-LOPEZ, Monica; ALMANSA-ROSALES, Carmen; LLORENTE-FERNANDEZ, Ana Virginia; CHRISTMANN, Ute; RODRIGUEZ ESCRICH, Sergio; (355 pag.)WO2017/198339; (2017); A1;,
Tetrahydropyran – Wikipedia
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156353-01-4, N-Methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Add 2 M isopropylmagnesium chloride in tetrahydrofuran (520.22 mL, 3.0 eq) to a mixture of methyl tetrahydro-2H-pyran-4-carboxylate (46.30 mL, 346.81 mmol) and Nu,Omicron-dimethylhydroxylamine hydrochloride (52.44 g, 1.6 eq) in tetrahydrofuran (2.43 L) during 15 minutes at -20C under nitrogen. After 30 min, add saturated aqueous ammonium chloride (400 mL) to the reaction at -20C. Extract the aqueous solution with methyl tert-butyl ether (250 mL x 3). Wash the combined organics with saturated aqueous sodium chloride. Dry over anhydrous magnesium sulfate and concentrate in vacuo. Add dichloromethane (500 mL), filter through Celite and concentrate in vacuo. Add tetrahydrofuran (700 mL), then add 3 M methyl magnesium chloride intetrahydrofuran (231.21 mL, 2.0 eq) dropwise over 15 minutes at 7C. After 40 minutes, add saturated aqueous ammonium chloride (250 mL) to the reaction. Extract the aqueous solution with methyl tert-butyl ether (250 mL x 2). Dry over anhydrous magnesium sulfate and concentrate in vacuo. Purify by silica gel chromatography, eluting with 2: 1 hexanes: ethyl acetate to 1 : 1 hexanes: ethyl acetate, to give 1 -(tetrahydro-pyran-4-yl)- ethanone (33.18 g, 75%). ‘H NMR (300 MHz, DMSO-d6) delta 3.98 (m, 2H), 3.42 (m, 2H), 2.52 (m, 1H), 2.15 (s, 3H), 1.74 (m, 4H)., 156353-01-4

156353-01-4 N-Methoxy-N-methyltetrahydro-2H-pyran-4-carboxamide 23144693, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ELI LILLY AND COMPANY; BEIGHT, Douglas, Wade; BURKHOLDER, Timothy, Paul; CLAYTON, Joshua, Ryan; EGGEN, MariJean; HENRY, Kenneth, James, Junior; JOHNS, Deidre, Michelle; PARTHASARATHY, Saravanan; PEI, Huaxing; REMPALA, Mark, Edward; SAWYER, Jason, Scott; WO2011/50016; (2011); A1;,
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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.,4295-99-2

Intermediate 54-(3~chloropropyl)-tetrahydro-2H-pyran-4-carbonitrile. To a stirred solution of 1 M LiHMDS (25 mL, 25 mmol) in THF (10 mL) at -78 0C was added dropwise a solution of intermediate 4 (2.23 g, 20 mmol) in THF (15 mL) over 10 minutes. After 40 min, l-chloro-3-iodopropane (2.7 mL, 25 mmol) was added at once, stirred at -78 C for 1 h and 4 h room temperature. Then the reaction mixture was diluted with ether (100 mL), washed with water (20 mL) and brine (20 mL), dried (Na2SO4), filtered and concentrated to give yellow oil which was purified by flash column chromatography using 10-30% EtOAc/Hexanes to afford the product intermediate 5 as a colorless liquid (3.737 g, 99%). 1H NMR (500 MHz, CDCl3) delta: 3.97 (2H, dd, J = 11.3, 3.7 Hz), 3.71 (2H, td, J = 12.2, 1.8 Hz), 3.61 (2H, t, J = 6.3 Hz), 2.05-1.98 (2H, m), 1.88 (2H, dd, J = 13.4, 1.8 Hz), 1.77-1.74 (2H, m), 1.65-1.59 (2H, m).

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/58646; (2007); 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.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.

1H (11.53 g, 35.03 mmol) was dissolved in dichloromethane (130 mL), cooled to 0 C A dess martin oxidant (29.72 g, 70.06 mmol)Was added to the reaction solution in portions and allowed to stand at room temperature for 4 hours.The solution was cooled to 0 C, saturated sodium bicarbonate solution (60 mL) was added dropwise to the reaction mixture, stirred for 20 minutes, filtered, the filtrate was allowed to stand,The aqueous phase was extracted with methyl tertiary butyl ether (60 mL x 3) and the combined organic phases were washed with saturated sodium bicarbonate solution (30 mL x 2). The organic phase was dried over anhydrous sodium sulfate,(10.85 g, yield 94.7%) as a white crystalline powder, and the residue was purified by column chromatography (petroleum ether / ethyl acetate (v / v) = 10: 1-4: 1).

1172623-99-2, As the paragraph descriping shows that 1172623-99-2 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.137052-08-5,1-(Tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

(i?)-2-Methylpropanesulfinamide (106.9 g, 882.0 mmol) and titanium tetraethoxide (201.6 g, 883.6 mmol) were added to a solution of 4-acetyltetrahydropyran (112.5 g, 877.7 mmol) in THF (1.4 L) under an inert atmosphere and the mixture heated to reflux for 18 h. The mixture was allowed to cool and poured in to brine (850 mL). The resulting slurry was diluted with EtOAc (1 L) and the mixture filtered through celite. The resulting two phases were separated. The filter cake was washed with EtOAc (4 x 1 L) and the combined organics dried (Na2S04), filtered and concentrated under vacuum (40-45C) to give a cloudy oil that was filtered to afford the desired material (192.5 g, 95%) as a yellow oil which was used without further purification., 137052-08-5

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

Reference£º
Patent; ASTRAZENECA AB; PIKE, Kurt, Gordon; BARLAAM, Bernard, Christophe; (85 pag.)WO2017/162605; (2017); 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

General procedure: To a solution of appropriate crude acid (1 eq) in CH2Cl2 wereadded EDCI (3 eq), DMAP (0.3 eq) and DIPEA (3 eq). The solutionwas stirred at room temperature for 0.5 h and compound 23 [7] (0.8eq) was added. The resulting mixture was stirred for another 8 hand water was added. The layers were separated, and the aqueouslayer was extracted with CH2Cl2. The combined organic layer waswashed with brine, dried over anhydrous Na2SO4, filtered, andconcentrated under vacuo. The residue was prified by chromatography(CH2Cl2/CH3OH 40:1) to provide target compounds 27a-i,28a-d and 34a-c., 1228779-96-1

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

Reference£º
Article; Liu, Xiaohua; Zhang, Yu; Huang, Wenjing; Luo, Jia; Li, Yang; Tan, Wenfu; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 149 – 165;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

61363-56-2, 2H-Pyran-3,5(4H,6H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,61363-56-2

To a solution of(1R)-5-fluoroindan-1- amine, J-32, (980 mg, 5.2 mmol, 1 eq, HC1 salt) in 10 mL of 1,2-dichloroethane was added TEA (529 mg, 5.2 mmol, 727 .iL, 1 eq) for neutralization at 15C. Then tetrahydropyran-3,5- dione (596 mg, 5.2 mmol, 1 eq) and HOAc (31.4 mg, 522 imol, 0.1 eq) was added. The reaction was stirred for 1 hour at 80C. The reaction mixture was concentrated under reducedpressure to give the cmde product, which was purified by column chromatography (Si02, eluting with a gradient of petroleum ether: ethyl acetate = 10:1 to 0:1) to give 820 mg of compound J-33 (63% yield) as a yellow solid.

As the paragraph descriping shows that 61363-56-2 is playing an increasingly important role.

Reference£º
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (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.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Example 7: Preparation of f3R)-5-methyl-3-(2-oxo-2(ralphaR)-l-phenylethyl1amino)ethvn hexanoic acid compound (24); [0081] A three-necked flask equipped with an addition funnel, thermometer pocket, drying tube and a mechanical stirrer, was charged with ethyl acetate (100 ml), (R)-(+)- phenylethylamine (35.58 g, 0.147mole) and 4-dimethylaminopyridine (0.18 g, 0.00147 mole). The mixture was cooled to a temperature of 0-5 C, followed by addition of a solution of 3-isobutyl glutaric anhydride (25 g, 0.147 mole) in ethyl acetate (25 ml), over a period of 15-20 minutes, and stirring for additional 1.5-2 hours, at a temperature of 0-5C. The solvent was stripped off and the residue was extracted with 2.5-3 percent aqueous solution of NaHCO3 solution (500 ml), and diluted with water (1000 ml) followed by washing the aqueous phase with toluene (1 x 100 ml and 1 x 50 ml). The pH of the aqueous phase was adjusted to 2-2.5 by adding a 1-12 N solution of hydrochloric acid. The aqueous phase was further extracted with ethyl acetate (1 x 150 ml and 1 x 50 ml), followed by drying the combined ethyl acetates extracts over anhydrous sodium sulfate, and stripping off the solvents, to obtain a residue. The residue was crystallized from ethyl acetate and toluene mixture to get 26.6 g (61.5 percent yield) of a white solid of (3R)-5-methyl-3-(2-oxo-2- {[(lR)-l-phenylethyl]amino}ethyl)hexanoic acid with an optical purity of 99.3 percent, as measured by chiral HPLC.

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; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2007/35789; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

624734-17-4, To a solution of the product from Step A (50 mg, 0.39 mmol) in methylene chloride (15 mL) was added Intermediate 4 (128 mg, 0.32 mmol) and N, N-DIISOPROPYLETHYLAMINE (203 uL, 1.17 mmol). After adding molecular sieves (15 mg), sodium triacetoxyborohydride (827 mg, 3. 9 mmol) was added and mixture stirred overnight. The mixture was extracted with methylene chloride, washed with sodium bicarbonate, dried under sodium sulfate and concentrated in vacuo. The crude product was purified on preparation plates (10/89/1, methanol/methylene chloride/ammonium hydroxide). 4 N hydrochloric acid was added and the solution was concentrated in vacuo to yield Example 2 (40 mg, 28%). LC-MS: MW calculated 443.24, found 444.5.

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

Reference£º
Patent; MERCK & CO., INC.; WO2005/14537; (2005); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1768-64-5, 4-Chlorotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A suspension of intermediate A (O. lg, 0.47mmol), 4-chlorotetrahydro-2H-pyran (leq) and potassium carbonate (2eq) in DMF (3mL) was stirred at 80C for 18h. LC-MS indicated that the reaction was not complete so further 4-chlorotetrahydro-2H-pyran (leq) and potassium carbonate (leq) were added and the mixture stirred at 80C for 24h. Further 4- chlorotetrahydro-2H-pyran (2eq) and potassium carbonate (2eq) were again added and the mixture stirred at 80C for 72h. After cooling to rt, the mixture was treated with H20 and extracted with dichloromethane. The organic phase was collected and dried using a hydrophobic frit then concentrated in vacuo. The resultant residue was purified by prep. HPLC to give the title product. 1H NMR (d6-DMSO) delta 9.77 (s, 1H), 8.90 (s, 1H), 8.02 (s, 1H), 7.61 (s, 1H), 4.84 (s, 1H), 4.02 (dd, 2H), 3.84 (s, 3H), 3.58 (t, 2H), 2.20 (td, 2H), 1.90 (dd, 2H); LC-MS method B, (ES+) 300, RT = 6.36 min.

1768-64-5, The synthetic route of 1768-64-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CELLZOME LIMITED; HARRISON, Richard, John; OXENFORD, Sally; HOBSON, Andrew; RAMSDEN, Nigel; MILLER, Warren; WO2011/134831; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics