Category: Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.108-55-4,Dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

To a stirred suspension of aluminum chloride (205.85g, 1. 54MOL) in dichloromethane(500ML) was added a solution of glutaric anhydride (80g, 0. 7MOL) indichloromethane (125ML) at 0C. The reaction mass was stirred for30minutes and fluorobenzene (67.36g, 0. 7MOL) was added to the reactionmass slowly. The reaction was monitored for completion by TLC and thenpoured into ice cold water (2000ML) under stirring and the separatedsolids were collected by filtration. The solids were dissolved in 3%aqueous sodium hydroxide solution (1100ML) and washed withdichloromethane (300ML). The aqueous layer was acidified to give aprecipitate. The solids were filtered and washed with water andvacuum-dried to yield the title product (125g, yield: 85%). LHNMR(CDC13) 8 : 8.027-7. 98 (M, 2H), 7.17-7. 11 (M, 2H), 3.067 (t, 2H), 2.52(t, 2H), 2.14-2. 04 (M, 2H).

As the paragraph descriping shows that 108-55-4 is playing an increasingly important role.

Reference£º
Patent; RANBAXY LABORATORIES LIMITED; WO2004/99132; (2004); A2;,
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.5631-96-9,2-(2-Chloroethoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A reaction vessel is charged with tert-butyl 3,6,8-trioxo-2-(4-(prop-2-yn-1-yloxy)phenyl)- 2,7-diazaspiro[4.5]decane-7-carboxylate (1 equiv.), potassium carbonate (2 equiv.) and DMF (0.5 M).2-(2-Chloroethoxy)tetrahydro-2H-pyran (1.1 equiv.) is added and the reaction is heated at 110 C for 12 hours. The reaction is then cooled to ambient temperature and concentrated. The residue is taken up in water and ethyl acetate and the layers separated. The aqueous layer is extracted with ethyl acetate (2x). The combined organic layer is washed with brine, dried over sodium sulfate, filtered and concentrated. The crude residue is used directly in the following reaction.

5631-96-9 2-(2-Chloroethoxy)tetrahydro-2H-pyran 254951, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; LAZARSKI, Kiel; MICHAEL, Ryan, E.; (771 pag.)WO2017/197036; (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.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

EXAMPLE IG 4- {4-[(4′-chloro- 1 , 1 ‘-biphenyl-2-yl)methyl]piperazin-l -yl} -N-( {3-nitro-4-[(tetrahydro-2H- pyran-4-ylmethyl)amino]phenyl}sulfonyl)-2-phenoxybenzamide; EXAMPLE IE (90 mg), EXAMPLE IF (45 mg), l-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (65 mg), and 4-dimethylaminopyridine (22 mg) were stirred in CH2Cl2 (4 mL) for 24 hours. The reaction was cooled and chromatographed on silica gel with 20- 100% ethyl acetate/hexanes. H NMR (300MHz, dimethylsulfoxide-d6) delta 11.55 (brs, IH), 8.63 (t, IH), 8.47 (d, IH), 7.75 (d, IH), 7.46 (m, 6H), 7.35 (m, 2H), 7.24 (m, 3H), 7.15 (d, IH), 6.99 (dd, IH), 6.82 (d, 2H), 6.75 (d, IH), 6.38 (d, IH), 3.86 (br d, 2H), 3.49 (m, 2H), 3.37 (br s, 2H), 3.15 (br s, 4H), 2.34 (br s, 4H), 1.91 (br s, 4H), 1.64 (br d, 2H), 1.29 (m, 3H).

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

Reference£º
Patent; ABBOTT LABORATORIES; BRUNCKO, Milan; DING, Hong; DOHERTY, George, A.; ELMORE, Steven, W.; HASVOLD, Lisa; HEXAMER, Laura; KUNZER, Aaron, R.; MANTEI, Robert, A.; MCCLELLAN, William, J.; PARK, Chang, H.; PARK, Cheol-min; PETROS, Andrew, M.; SONG, Xiaohong; SOUERS, Andrew, J.; SULLIVAN, Gerard, M.; TAO, Zhi-fu; WANG, Gary, T.; WANG, Le; WANG, Xilu; WENDT, Michael, D.; WO2010/65865; (2010); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1240390-36-6, tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(3R,4R)-4-(6-Carbamoyl-5-(6-isopropoxypyridin-2-ylamino)pyridazin-3-ylamino)tetrahydro-2H-pyran-3-ylcarbamate [0524] [0525] To a solution of 6-chloro-4-(6-isopropoxypyridin-2-ylamino)pyridazine-3-carboxamide (270 mg, 877 mumol, Eq: 1.00) in NMP (3.51 mL) was added tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (190 mg, 877 mumol, Eq: 1.00) and the mixture heated to 140 C. Over the next 36 hrs three additional portions of amine were added at 12 h intervals. At 48 hrs the mixture was cooled, diluted with EtOAc, and washed with water and brine (2¡Á). The organic layer was concentrated onto silica and purified by chromatography (70% to 100% EtOAc/hexanes) to (3R,4R)-4-(6-carbamoyl-5-(6-isopropoxypyridin-2-ylamino)pyridazin-3-ylamino)tetrahydro-2H-pyran-3-ylcarbamate (190 mg, 44.4%). 1H NMR (400 MHz, CHLOROFORM-d6) delta ppm 11.37 (s, 1H), 8.06 (s, 1H), 7.92 (s, 1H), 7.49 (t, J=7.5 Hz, 1H), 6.44 (d, J=8.0 Hz, 1H), 6.31 (d, J=8.2 Hz, 1H), 5.91 (s, 1H), 5.67 (s, 1H), 5.38 (d, J=8.5 Hz, 1H), 5.15 (m, 1H), 4.30 (m, 1H), 4.05 (s, 1H), 4.00 (d, J=12.5 Hz, 1H), 3.90 (d, J=12.3 Hz, 1H), 3.68 (d, J=11.3 Hz, 1H), 3.61 (t, J=10.8 Hz, 1H), 2.27 (s, 1H), 1.79 (m, 1H), 1.44 (m, 15H).

1240390-36-6 tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate 68077633, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Hoffman-La Roche Inc.; Hermann, Johannes Cornelius; Kennedy-Smith, Joshua; Lucas, Matthew C.; Padilla, Fernando; Soth, Michael; US2013/178478; (2013); 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

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.; A mixture of compound 2,2-dimethyl-3 ,6-dihydro-2H-pyran-4-yltrifluoromethanesulfonate and 6,6-dimethyl-3 ,6-dihydro-2H-pyran-4-yltrifluoromethanesulfonate (134) (200 g, 0.77 mol, 1.0 eq.), bis(pinacolato)diboron (135) (195 g, 0.77 mol, 1.0 eq.), and potassium acetate (151 g, 1.54 mol, 2.0 eq.) in dioxane (2 L) was degassed for 15 min, to it was added l,l ‘-bis(diphenylphosphino)ferrocene- palladium(II)dichloride dichloromethane complex (19 g, 0.023 mol, 0.03 eq.) and the reaction mixture was degassed again for 15 min. The reaction mixture was heated to 80 C overnight, cooled, filtered through a medium fritted funnel, and washed with MTBE (300 mL X 4). The organic extracts were combined and concentrated under reduced pressure. The crude product mixture (136) was cooled using an ice bath, stirred with an overhead stirrer and to it was added aqueous 2M NaOH solution (2 L) keeping the internal temperature below 15 C. The basic aqueous solution was extracted with MTBE (250 mL X 3), and the organic extracts were discarded. The aqueous phase was cooled using an ice bath and the pH was adjusted to 3 to 5 with concentrated HC1 keeping the internal temperature below 10 C. The heterogeneous solution (off-white solid precipitated out at pH 3~5) was extracted with EtOAc (3 L and 1.5 L). The combined organic layer was washed with water (1 L), brine (1 L), dried over Na2S04, filtered and concentrated. The crude product mixture (136) was purified by columnchromatography (Hexanes? 15% ethyl acetate in hexanes, R = 0.5, visualized on KMn04) to give 125 g of 2-(2,2-dimethyl-3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-l,3,2- dioxaborolane and 2-(6,6-dimethyl-3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-l,3,2- dioxaborolane mixture (136) as a white solid (58% overall yield, >97%> purity by GCMS and 1H NMR, The ratio of regioisomers was found to be 80.4: 19.6).GCMS: >97%1H NMR (300 MHz, CDC13) delta 6.46 – 6.43 (m, 1H), 4.06 (q, 2H, J=3.0 Hz), 1.96 – 1.94 (m, 2H),1.20 (s, 12H), 1.09 (s, 6H)GCMS: 239 (M+l); calcd for Ci3H23B03: 238.13

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

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

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

Reference Example 4: Synthesis of 7-[4-(tetrahydropyran-4-ylmethoxy)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylamine 7-(4-hydroxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylamine (the compound obtained in Reference Example 3; 295 mg) was dissolved in N,N-dimethylformamide (8 ml). Thereafter, tetrahydropyran-4-ylmethyl p-toluenesulfonate (460 mg) and cesium carbonate (556 mg) were added to the obtained solution, and the obtained mixture was stirred at 90C overnight. After the reaction solution was cooled to a room temperature, distilled water (18 ml) was added thereto. The generated precipitate was collected by filtration, and the obtained product was then washed by successive suspension in a 20% ethanol solution, ethanol, and acetone to obtain the captioned compound (310 mg).

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

Reference£º
Patent; NIPPON KAYAKU KABUSHIKI KAISHA; EP1630165; (2006); 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.

Preparation 46 1 -(tetrahydro-2H-pyran-4-yl)cyclopropanamine [0227] Combined tetrahydro-2H-pyran-4-carbonitrile (1.000 g, 9.00 mmol) and titanium (rV)isopropoxide (2.90 mL, 9.90 mmol) in ether (45.0 mL), then ethylmagnesium bromide (6.60 mL, 19.79 mmol) was added and the reaction was allowed to warm to room temperature for 1 hour. The reaction was stirred for an additional 30 minutes and boron trifluoride etherate (2.280 mL, 18.0 mmol) was added and the reaction was stirred for 2 hours. The reaction was then diluted with 10 mL water and 20 mL 1 N HC1 and extracted twice with 200 mL EtOAc. The organic layers were combined and concentrated to afford the title compound (850 mg, 53.5%) as a yellow oil.

The synthetic route of 4295-99-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; DAVIS, Melinda; IVETAC, Anthony; JONES, Benjamin; KIRYANOV, Andre, A.; KUEHLER, Jon; LANIER, Marion; MIURA, Joanne; MURPHY, Sean; WANG, Xiaolun; WO2014/160810; (2014); 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

Preparation 4: Methanesulfonicacid (tetrahydropyran-4-yl)methyI ester; To a mixture of Preparation 3 (216.5g, 1.87mol) and triethylamine (299mL) in DCM (1.3L) at <10C was added under argon a solution of methanesulfonyl chloride (236g, 160mL)in DCM (200mL) over 2h 50min, maintaining the temperature at 5-10C throughout. Subsequent washing with water (1L), 1M HC1 (500mL), 5% NaHC03 (300mL), water (300mL), drying (MgS04) and then removal of the solvent afforded the title compound (328g, 90% yield). NMR was consistent with the above structure. 14774-37-9 Tetrahydropyran-4-methanol 2773573, aTetrahydropyrans compound, is more and more widely used in various. Reference£º
Patent; PROSIDION LIMITED; WO2006/16174; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1245724-46-2, (S)-Tetrahydro-2H-pyran-3-amine hydrochloride is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(3S)-Tetrahydro-2H-pyran-3-amine hydrochloride (1.99 g, 14.5 mmol) in MeCN (10 ml) was added dropwise to a mixture of DIPEA (6.30 ml, 36.2 mmol) and ethyl 2,4- dichloropyrimidine-5-carboxylate (3.2 g, 14.5 mmol) in MeCN (60 ml) at 0C over a period of 5 minutes under air. The reaction mixture was stirred for 4 h, slowly allowing to warm to rt as the ice bath melted. The reaction mixture was stirred at rt for 18 h. The reaction mixture was evaporated to dryness to remove MeCN, diluted with EtOAc (100 mL), and washed with water then sat. brine. The organic layer was dried over MgS04, filtered and evaporated to afford crude product. The crude product was purified by fee, eluting with 0 – 40% EtOAc in heptane to afford the title compound (3.24 g, 78%) as a yellow oil;lH NMR (400 MHz, DMSO) 1.32 (3H, t), 1.49 – 1.6 (1H, m), 1.63 – 1.79 (2H, m), 1.83 – 1.94 (1H, m), 3.48 (1H, dd), 3.54 – 3.65 (2H, m), 3.74 (1H, dd), 4.08 – 4.19 (1H, m), 4.33 (2H, q), 8.57 (1H, d), 8.64 (1H, s); m/z [M-H]-284.

As the paragraph descriping shows that 1245724-46-2 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; CANCER RESEARCH TECHNOLOGY LIMITED; FINLAY, Maurice, Raymond, Verschoyle; GOLDBERG, Frederick, Woolf; TING, Attilla, Kuan, Tsuei; (103 pag.)WO2018/114999; (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.108-55-4,Dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

EXAMPLE 2; Synthesis of Mono-carbonyl butanoic acid 3; To a solution of 2.01 g (5.46 mmol) of curcumin, 1 12 mg (0.92 mmol) of DMAP, and 0.685 g (6 mmol) glutaric anhydride (95%) in 100 ml THF was added 1.33 ml (9.55 mmol) Et3N. The reaction was stirred at reflux under argon overnight. Purified on column chromatography, eluting with CH2Cl2-CH2Cl2)MeOH, 95:5. Yield 84%. NMR 1H (CDCl3), delta (ppm): compound (3),1.97-2.14 (m, 2H); 2.43-2.79 (m, 4H); 3.87-3.95 (d, 6H); 5.83 (s, 2H); 6.45-6.59 (t, 2H); 6.91-7.18 (m, 6H); 7.57-7.65 (d, 2H). 13C NMR (CDCl3), delta (ppm): 19.98; 32.76; 55.82; 101.61 ; 109.86; 1 1 1.36; 1 15.04; 120.95; 121.54; 123.05; 124.16; 127.35; 133.89; 139.38; 139.99; 141.06; 147.03; 148.22; 151.23; 170.98; 177.374; 181.73; 184.65. MS (ESI) calcd. for C26H26O9: 482.48; found: 483.2 [M+H]+. See Robert E. Gawley; Mykhaylo Dukh; Claudia M. Cardona; Stephan H. Jannach; Denise Greathouse. Org. Lett.., Vol. 7, No. 14, 2005.2953-2956.

As the paragraph descriping shows that 108-55-4 is playing an increasingly important role.

Reference£º
Patent; RESEARCH FOUNDATION OF THE CITY UNIVERSITY OF NEW YORK; WO2008/45534; (2008); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics