Tag: M.W:100-200

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

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

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;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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
Tetrahydropyran – an overview | ScienceDirect Topics

14774-37-9, Tetrahydropyran-4-methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To 5.00 g (43.0 mmol) of (tetrahydro-pyran-yl)-methanol in DCM (50 mL) are added 67 mg of 2,2,6,6-tetramethyl-1-piperidinyloxy (0.43 mmol), a solution of 9.04 g (108 mmol) NaHCO3 in water (70 mL) and 512 mg (4.30 mmol) of potassium bromide at 20 C. The suspension is cooled in an ice bath to 4 C. Then a solution of 23.5 mL sodium hypochlorite (10-15% free chlorine; 47.4 mmol) is added in 35 min. The suspension is stirred for 30 min at 4-9 C. and further 45 min to reach 17 C. 4.80 mL sodium hypochlorite (10-15% free chlorine) is added within 15 min. The reaction is stirred for 16 h at RT. The suspension is filtered and the layers are separated. The aq. layer is washed with 50 mL DCM, the combined organic layers are washed with 50 mL water. The solvent is removed under reduced pressure to afford 3.00 g of tetrahydro-pyran-4-carbaldehyde. Yield: 61%; ESI-MS: 113 [M+H]-

14774-37-9, The synthetic route of 14774-37-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Boehringer Ingelheim International GmbH; Riether, Doris; Binder, Florian Paul Christian; Doods, Henri; Mueller, Stephan Georg; Nicholson, Janet Rachel; Sauer, Achim; US8865744; (2014); B1;,
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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

To a solution of 7,7-dimethyloxepan-4-one and 2,2-dimethyloxepan-4-one (2.6 g, 18.3 mmol) and pyrrolidine (85 mg, 1.2 mmol) in dimethyl sulfoxide (20 mL) was slowly added ethyl diazoacetate (1.39 g, 12.2 mmol). After addition, the reaction was stirred at 22 C for 16 h and poured into water (30 mL). The mixture was then extracted with ethyl acetate (3 x 30 mL).The combined organic layers were washed with water (2 x 30 mL) and brine (30 mL), dried over sodium sulfate and concentrated to dryness in vacuo. The residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 18% ethyl acetate in petroleum ether) to afford a mixture of three regio-isomers (900 mg, 20.6% yield) as yellow oil. The regio-isomers were separated by SFC to afford: Peak 1 (Rention time 3.31 min), ethyl 5,5-dimethyl-4,5,7,8-tetrahydro-1H-oxepino[4,5-c]pyrazole-3-carboxylate (200 mg): 1H MR (400 MHz, CDC13) delta 4.38 – 4.33 (m, 2H), 3.88 (t, J = 6.0 Hz, 2H), 3.11 (s, 2H), 2.97 (t, J= 6.00 Hz, 2H), 1.37 (t, J= 6.00 Hz, 2H), 1.21 (s, 6H) Peak 2 (Rention time 3.37 min), ethyl 7,7-dimethyl-4,5,7,8-tetrahydro-1H-oxepino[4,5-c]pyrazole-3-carboxylate (150 mg) as a yellow oil: NMR (400 MHz, CDC13) delta 4.39 – 4.34 (m, 2H), 3.92 – 3.87 (m, 2H), 3.08 – 3.03 (m, 2H), 2.98 (s, 2H), 1.38 (t, J= 6.0 Hz, 3H), 1.23 (s, 6H) Peak 3 (Rention time 6.30 min), ethyl 6,6-dimethyl-4,5,6,8-tetrahydro-1H-oxepino[3,4-c]pyrazole-3-carboxylate (150 mg) as a yellow oil: 1H MR (400 MHz, CDC13) delta 4.68 (s, 2H), 4.40 – 4.35 (m, 2H), 3.00 – 2.92 (m, 2H), 1.95 – 1.88 (m, 2H), 1.39 (t, J = 6.0 Hz, 3H), 1.33 (s, 6H). SFC conditions: Column: Chiralpak AD-3 150×4.6mm I D., 3um Mobile phase: A: C02 B: ethanol (0.05% DEA) Gradient: from 5% to 40% of B in 5 min and hold 40% for 2.5 min, then 5% of B for 2.5 min Flow rate: 2.5mL/min Column temp.: 35C Column: Chiralpak AY 150×4.6mm ID., 3um Mobile phase: A: C02 B: iso-propanol (0.05% DEA) Gradient: from 5% to 40% of B in 5 min and hold 40% for 2.5 min, then 5 for 2.5 min Flow rate: 2.5mL/min Column temp.: 35C, 1194-16-7

The synthetic route of 1194-16-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; PATEL, Snahel; HAMILTON, Gregory; STIVALA, Craig; CHEN, Huifen; ZHAO, Guiling; (1236 pag.)WO2017/4500; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

25637-16-5, 4-Bromotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

K2C03 (0.16 g, 1 .20 mmol) followed by ethyl iodide (0.07 mL, 0.90 mmol) were added at RT to a solution of compound 67b (0.20 g, 0.60 mmol) in dry DMF (7 mL) and the reaction mixture was stirred at RT for 48 h. Crushed ice was added and the mixture was extracted with EtOAc. The organic phase was washed with water and brine, dried over Na2S04 and evaporated. The residue was purified by flash column chromatography [silica; hexane with 5% EtOAc]. White solid. Yield: 0.15 g (69%). HPLC (method 1 ): Rt = 2.67 min, m/z [M+H]+ = 362.0 (MW calc. 361.41 ). H NMR (400 MHz, DMSO-d6, delta ppm): 8.82 (s, 2H), 8.03 (d, 1 H, J = 1.96 Hz), 7.68-7.64 (m, 1 H), 7.48-7.43 (m, 1 H), 7.38-7.32 (m, 2H), 6.71 (d, 1 H, J = 8.1 Hz), 6.50-6.48 (m, 1 H), 4.22 (s, 2H), 4.03-3.98 (m, 2H), 1 .35-1 .32 (m, 3H), 1.10-1.02 (m, 4H).Prepared from compound 67b and 4-bromotetrahydro-2H-pyran in analogy to procedure 67c. White solid. Yield: 10 mg. MS: m/z: [M+H] = 418.1 (MW calc. 417.19)., 25637-16-5

25637-16-5 4-Bromotetrahydropyran 13349654, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; GRUeNENTHAL GMBH; KONETZKI, Ingo; JAKOB, Florian; WAGENER, Markus; WELBERS, Andre; HESSLINGER, Christian; (138 pag.)WO2017/108203; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

EXAMPLE 30 4-(4-bromo-3-chlorophenyl)-1-methyl-1,2,4,9-tetrahydropyrano[3,4-b]pyrazolo[4,3-e]pyridine-3,5(6H,8H)-dione 2H-Pyran-3,5(4H,6H)-dione (0.057 g, 05 mmol), 3-chloro4-bromo-benzaldehyde (0.11 g, 0.5 mmol), and 5-amino-1-methyl-1,2-dihydropyrazol-3-one (0.056g, 0.5 mmol) were processed as described in Example 26C to provide 0.145 g of the title compound. 1H NMR (300 MHz, DMSO-d6)6 3.5 (s, 3H), 4.0 (s, 2H), 4.52 (q, 2H), 4.92 (s, 1H), 7.03 (dt, 1H), 7.32(t, 1H), 7.6 (dd, 1H), 9.62 (s, 1H), 10.1 (s, 1H); MS (ESI-) m/z 410 (M+H:) Anal. calcd for C16H13N3BrClO3: C, 46.80;H,3.19; N, 10.23. Found: C, 46.77;H, 3.43; N, 10.27.

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

Reference£º
Patent; Drizin, Irene; Altenbach, Robert J.; Carroll, William A.; US2002/7059; (2002); 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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

A solution of 2,2-dimethyltetrahydropyran-4-one (133) (115 g, 0.9 mol, 1.0 eq.) in anhydrous THF (600 mL) was cooled to -78 C and to it was added LDA (2.0 M, 538 mL, 1.08 mol, 1.2 eq.) drop wise under N2 keeping the internal temperature below -65 C. The resulting solution was stirred at -78 C for 20 min. A solution of N-phenyl- bis(trifluoromethanesulfonimide) (353 g, 0.99 mol, 1.1 eq.) in anhydrous THF (1900 mL) was added to the above solution slowly keeping the internal temperature below -65 C. The reaction mixture was warmed to room temperature slowly and stirred overnight. The reaction was quenched with saturated aqueous sodium bicarbonate solution, and extracted with MTBE (2 L X 2). The combined organic layers was washed with 10% aqueous NaOH solution (1 L X 2), brine (500 mL X 2), dried over Na2S04, filtered and concentrated to give crude title triflate product mixture as dark brown oil. The crude product was extracted with hexanes (2 L X 5) and the combined hexanes extracts was purified by column chromatography (directly loaded onto silica gel, Hexanes? 15% ethyl acetate in hexanes, R/= 0.6, visualized with KMn04 stain) to give 200 g of the triflate product mixture (134) (a mixture of 2,2-dimethyl-3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate and 6,6-dimethyl-3 ,6-dihydro-2H-pyran-4-yltrifluoromethanesulfonate ratio = 80.6: 19.4 by GCMS) as a light yellow liquid (~ 90% purity by GC-MS and 1H NMR). This was taken to the next step without further purification.

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; AMGEN INC.; ALLEN, Jennifer R.; CHEN, Jian J.; FROHN, Michael J.; HU, Essa; LIU, Qingyian; PICKRELL, Alexander J.; RUMFELT, Shannon; RZASA, Robert M.; ZHONG, Wenge; WO2011/143365; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

14774-37-9, Tetrahydropyran-4-methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: Synthesis of B-3Prepared as described by adaptation of the following literature reference:Radziszewski, J.G. et al. J. Am. Chem. Soc. 1993, 115, 8401.To a solution of 97 g (810 mmol) of compound B-2 in 2-methyltetrahydrofuran (190 mL) are added 165 mL of 50% aqueous NaOH solution. To this stirred suspension is added dropwise with cooling a solution of p-toluene-sulfonylchloride (283 g, 1.46 mol) in 2- methyltetrahydrofuran (280 mL). The reaction is stirred at 30-35 C for 18 h. The suspension is poured into a mixture of ice-water (280 mL) and aqueous HCl solution (37%, 203 mL). After addition of methylcyclohexane (1.4 L) and further ice-water (0.2 L), the reaction mixture is stirred for 2 h in an ice-bath. The resulting crystalline precipitate is isolated by filtration and washed with methylcyclohexane (0.5 L) and water (0.5 L).Drying under reduced pressure at 40 C gave 216 g of compound B-3 as white crystalline solid. Yield: 99%, ES-MS: m/z 271 [M+H]; *H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.19 – 1.35 (2 H, m), 1.54 – 1.63 (2 H, m), 1.85 – 2.02 (1 H, m), 2.45 (3 H, s), 3.28 – 3.39 (2 H, m), 3.86 (2H, d, J=6.60 Hz), 3.93 (2 H, dd, J=l 1.37, 4.52 Hz), 7.35 (2 H, d, J=9.29 Hz), 7.78 (2 H, d, J=8.31 Hz)

14774-37-9, 14774-37-9 Tetrahydropyran-4-methanol 2773573, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HICKEY, Eugene Richard; RIETHER, Doris; ERMANN, Monika; WO2012/12307; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics