Category: Tetrahydropyrans

65412-03-5, 4-(2-Aminoethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 63-(Phenylsulfonyl)-lambda/-[2-(tetrahydro-2H-pyran-4-yl)ethyl]-8-quinolinamine hydrochloride (E6)To 8-fluoro-3-(phenylsulfonyl)quinoline (D2) (300 mg), potassium carbonate (0.288 g: 2 eq) and 4-amino-ethyl[2-(tetrahydro-2H-pyran-4-yl)ethyl]amine (Apollo Scientific) (0.269 g, 2 eq) in DMSO(3 ml) were added to a 5 ml microwave vial. The mixture was heated at 18O0C under microwave irradiation for 1 hour. The reaction mixture was diluted with sodium hydrogen carbonate (20 ml) and extracted with ethyl acetate (3 x 20 ml). The ethyl acetate layers were combined and evaporated. The residue obtained was purified using the Flashmaster Il (gradient 10-80% ethyl acetate on 50 g silica column) to give the free base of the title compound (0.255 g).NMR (400MHz1 Chloroform-d6) delta 1.31-1.41 (2H1 m), 1.65-1.71 (5H, m), 3.33-3.49 (4H, m), 3.94-3.97 (2H, m), 6.93 (1 H, d), 7.22 (1 H1 d), 7.52-7.62 (4H1 m), 8.00-8.03(2H, m), 8.75 (1 H, d), 9.07 (1 H, d) EPO LC/MS, t = 3.58min, Molecular ion observed (MH+) = 497 consistent with the molecular formula C22H24N2O3S

As the paragraph descriping shows that 65412-03-5 is playing an increasingly important role.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2007/39220; (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.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Example 3: Preparation of (3RV5-methyl-3-r2-oxo-2{r(lR)-l-phenylethyl1ammo|ethvD hexanoic acid compound (24); [0077] A three-necked flask equipped with an addition funnel, thermometer pocket, drying tube and a mechanical stirrer, was charged with toluene (100 ml), (R)-(H-)- phenylethylamine (35.58 g, 0.294 mole) and 4-dimethylaminopyridme (0.18 g, 0.00147 mole). The mixture was cooled to a temperature of 0-50C, followed by addition of a solution of 3-isobutyl glutaric anhydride (25 g, 0.147 mole) in toluene (25 ml), over a period of 15-20 minutes, and stirring for additional 1.5-2 hours, at a temperature of 0-5C. The mixture was then extracted with 2.5-3.0 percent aqueous solution OfNaHCO3 solution (500 ml), and the aqueous phase was washed with toluene (1 x 100 ml). The pH of the aqueous phase was adjusted to 2-2.5 by adding a 1-12N 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 28.4g (66.4 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 99.6 percent, as measured by chiral HPLC.

The synthetic route of 185815-59-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2007/35789; (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.33024-60-1,Tetrahydro-2H-pyran-4-amine hydrochloride,as a common compound, the synthetic route is as follows.

Intermediate [II] (43mg, 0. [114MMOL)] was reacted with 4-amino-tetrahydropyran hydrochloride salt (31 mg, 0. [23MMOL)] according to general procedure C (0. [45MMOL] DIPEA in isopropanol, heated for 2.5hours). Purification by preparative HPLC gave the desired product (purine N-9 linked to the 1-position of ribose) as a yellow gum, [(18MG,] 0.041 mmol, 36percent). m/z 444 [(MH +),] LCMS retention time 2.64min. The isomeric product (purine [N-7-LINKED)] was also obtained as a gum, (6mg, 0. [014MMOL,] 12percent). m/z 444 (MH +), LCMS retention time 2.52min.

The synthetic route of 33024-60-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2004/26890; (2004); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tetrahydro-2H-pyran-3-ol (2.0 g) in DCM (100 mL) was added TEA(4.0 g) and methanesulfonyl chloride (2.7 g) at 0C under a nitrogen atmosphere. The resultingmixture was stirred at this temperature for 30 mins, and then quenched with aq. NaHCO3 solution. The mixture was extracted with DCM (2×50 mL). The combined organic phases were washed, dried and concentrated to afford tetrahydro-2H-pyran-3-yl methanesulfonate (3.2 g) as a brown oil.

The synthetic route of 19752-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CHEN, Weichun; IGBOKO, Ebere F; LIN, Xichen; LU, Hongfu; REN, Feng; WREN, Paul Bryan; XU, Zhongmiao; YANG, Ting; ZHU, Lingdong; WO2015/181186; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

29943-42-8, Dihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A: Preparation of 4-methylenetetrahydro-2H-pyran: A solution of dihydro-2H-pyran-4(3H)-one (2.50g; 25.0mmol) in THF (50mL) was sparged with nitrogen for 15 minutes. The solution was cooled to 5 C under nitrogen with stirring. A solution of Tebbe reagent (bis(cyclopentadienyl)-mu-chloro(dimethylaluminum)-mu-methylenetitanium) (25.0 mmol; 0.50 M solution in toluene; Sigma- Aldrich Chemical Co.) was added. The mixture was allowed to warm to ambient temperature. Ether was added (400 mL). The reagent was quenched by the careful addition of 0.1M sodium hydroxide (10 mL). (The quench is highly exothermic with considerable effervescence). The resulting solution was dried (sodium sulfate) and filtered through a mixture of Celite and alumina washing the filter cake with ether. The filtrate was partially concentrated to remove the majority of the ether at 50 C and a pressure of 580 mm Hg. The resulting mixture was diluted with pentane, filtered through Celite and then partially concentrated as previously (taking care not to lose the volatile product). The resulting solution in toluene/pentane was continued to the next step without characterization of the product.

29943-42-8 Dihydro-2H-pyran-4(3H)-one 121599, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; ARRAY BIOPHARMA INC.; BOYS, Mark Laurence; BURGESS, Laurence, E.; GRONEBERG, Robert, D.; HARVEY, Darren, M.; HUANG, Lily; KERCHER, Timothy; KRASER, Christopher, F.; LAIRD, Ellen; TARLTON, Eugene; ZHAO, Qian; WO2011/130146; (2011); 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.110238-91-0,Methyl tetrahydro-2H-pyran-4-carboxylate,as a common compound, the synthetic route is as follows.

Step 1: Synthesis of (Tetrahydro-pyran-4-yl)-methanol To a solution of 250 mL of LiAlH4 (2.3M solution in THF, 0.575 mol) in THF (200 mL) is added dropwise a solution of 130 mL (0.974 mol) of tetrahydro-pyran-4-carboxylic acid methyl ester in THF (900 mL) under nitrogen atmosphere (CAUTION: highly exothermic[reaction]). The temperature is kept at 40-45 C. with an ice-bath. Upon complete addition, the reaction is stirred at room temperature for 1.5 h. The reaction is cooled in an ice-bath and quenched with addition of water (22 mL), 15% aqueous NaOH solution (21 mL) and water (66 mL). The resulting precipitate is removed by filtration through Celite and is rinsed with THF (300 mL). The filtrate is concentrated under reduced pressure to afford 102.5 g of (tetrahydro-pyran-4-yl)-methanol as a clear oil. Yield: 91%; 1H-NMR (400 MHz, CHLOROFORM-d) delta ppm 1.20-1.39 (2H, m), 1.56-1.83 (3H, m), 2.03 (1H, br. s.), 3.29-3.52 (4H, m), 3.89-4.05 (2H, m),

110238-91-0 Methyl tetrahydro-2H-pyran-4-carboxylate 2773520, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Boehringer Ingelheim International GmbH; US2010/76029; (2010); 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.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A mixture of D147 (1 .00 g, 5.02 mmol), 2-(3-bromopropoxy)tetrahydro-2H-pyran (1 .12 g, 5.02 mmol) and K2CO3(1 .39 g, 10.04 mmol) in DMF (20 mL) was heated at 80 C for 3 hrs. The reaction mixture was poured into ice water (60 mL), and extracted with EtOAc (2×30 mL). The organic layer was washed with brine (3×40 mL), dried, filtered and concentrated. The crude was purified by column chromatography on silica gel (PE: EtOAc= 1 : 1 ) to give the title compound as a yellow solid (1 .526 g, yield 89%).

33821-94-2 2-(3-Bromopropoxy)tetrahydro-2H-pyran 2777988, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DING, Xiao; HO, Ming-Hsun; REN, Feng; YU, Haihua; ZHAN, Yang; (290 pag.)WO2019/12093; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Protocol A. To a suspension of the corresponding carboxylic acid 7-9 (0.25 mmol) in DMF (1 mL) were added DIEA (0.75 mmol, 3.0 eq), TBTU (0.325 mmol, 1.3 eq), HOBt (0.075 mmol, 0.3 eq) and the reaction mixture was stirred at rt for 5 min, followed by addition of the corresponding alcohol (1.1-5.0 eq). The reaction mixture was stirred at rt for 1-16h, then diluted with EtOAc (100 mL), washed with aqueous saturated sodium carbonate solution (50 mL), 0.1M HCl (50 mL), water (50 mL) and brine (50 mL). The organic phase was then dried over MgSO4 and concentrated under reduced pressure to afford the desired ester. Protocol B. To a solution of the corresponding carboxylic acid 7-9 (1.0 eq) in DCM were successively added DCC (1.0 eq), HOBt (1.0 eq) and DIEA (3.0 eq). The solution was stirred at rt for 30 minutes before the addition of the corresponding alcohol (1.1-5.0 eq). The reaction mixture was stirred at rt for 1-16h and then the solvent was removed in vacuo. The residue was partitioned between DCM and water and extracted with DCM. The organic layer was separated, washed consecutively with 2M sodium carbonate (or 1N NaOH), 1N HCl, brine, dried over MgSO4, and evaporated. Protocol C. To a solution of the corresponding carboxylic acid 7-9 (0.25 mmol) in THF or DCM (1 mL) cooled to 0 C was added 1-chloro-N,N,2-trimethyl-1-propenylamine, (0.5 mmol, 2.0 eq). The reaction mixture was stirred for 1-3h while warming up to rt, followed by addition of the corresponding alcohol (1.2 eq). The reaction mixture was stirred at rt for 1-16h and then the solvent was evaporated under reduced pressure. The residue was diluted with EtOAc and washed with saturated NaHCO3. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure.

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Reference£º
Article; Boland, Sandro; Defert, Olivier; Alen, Jo; Bourin, Arnaud; Castermans, Karolien; Kindt, Nele; Boumans, Nicki; Panitti, Laura; Van De Velde, Sarah; Stalmans, Ingeborg; Leysen, Dirk; Bioorganic and Medicinal Chemistry Letters; vol. 23; 23; (2013); p. 6442 – 6446;,
Tetrahydropyran – Wikipedia
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

A solution of tetrahydropyran-4-ol (2.0 g, 20 mmol) and diisopropylethylamine (3.00 g, 23.5 mmol) in DCM (20 mL) was cooled to 0 C and methanesulfonyl chloride (2.50 g, 21.5 mmol) was added drop wise and stirred at rt for 2 h. The mixture was concentrated to dryness to give the title Compound (3.72 mg, 100% yield), which was used in the next step directly

2081-44-9 Tetrahydro-2H-pyran-4-ol 74956, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CAI, Min; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; KREUTTER, Kevin; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; XIAO, Kun; ZHANG, Feihuang; ZHU, Yaoping; (528 pag.)WO2017/100662; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

To 15 mL methanol were added 2-(7-fluoro-1-(2-fluorobenzyl)-1H-indazol-3 -yl)pyrimidine-4 ,5, 6-triamine (0.20 g, 0.54 mmol) and1-(tetrahydro-2H-pyran-4-yl)ethanone (0.10 g, 0.78 mmol). Then acetic acid (0.16 mL, 2.8 mmol)was added at 0 C. The mixture was heated to room temperature and stirred for 1 hour, thencooled to 0 C, and to the mixture was added sodium cyanoborohydride (0.17 g, 2.7 mmol).Then the resulting mixture was stirred at room temperature overnight. The reaction mixture wasconcentrated in vacuo to remove the solvent, and to the residue was added saturated aqueoussodium bicarbonate ( 40 mL ). The resulting mixture was extracted with ethyl acetate (30 mL x 2).The combined organic layers were washed with water (50 mL) and saturated brine (50 mL),dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated on a rotaryevaporator and the residue was purified by silica gel chromatograph ( dichloromethane /methanol(v/v) = 200/1, 0.5% triethylamine) to give a light yellow solid (0.11 g, 42.0%) MS (ESI, pos.ion) m/z: 480.7 (M+ 1);1H NMR (400 MHz, DMSO-d6) 8 (ppm) 8.56 (d, J = 8.0 Hz, 1H), 7.38-7.30 (m, 1H), 7.27- 7.19 (m, 2H), 7.19-7.09 (m, 2H), 6.97 (t, J = 7.0 Hz, 1H), 5.90 (s, 4H), 5.81 (s, 2H), 3.96-3.85 (m, 2H), 3.31-3.21 (m, 3H), 2.89-2.76 (m, 1H), 1.82- 1.74 (m, 1H), 1.72- 1.64 (m, 1H),1.64-1.51 (m, 1H), 1.40-1.26 (m, 2H), 0.95 (d, J= 6.4 Hz, 3H);19F NMR (376 MHz, DMSO-d6) 8 (ppm) -118.77 (d, J = 7.1 Hz), -134.46 (d, J = 7.1 Hz).

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

Reference£º
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZUO, Yinglin; WANG, Xiaojun; YANG, Chuanwen; WANG, Jiancheng; CAO, Shengtian; WU, Fangyuan; ZHANG, Yingjun; GOLDMANN, Siegfried; (193 pag.)WO2018/188590; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics