Day: November 5, 2020

23462-75-1, Dihydro-2H-pyran-3(4H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a round-bottom flask equipped with a stir bar and placed under N2 atmosphere was added THF (50 mL), then trimethyl(trifluoromethyl)silane (1.03 mL, 6.99 mmol). The solution was cooled to 0 C and to the solution was added dihydro- 2H-pyran-3(4H)-one (500 mg, 4.99 mmol). The solution was stirred for 5 minutes at 0 C and then was allowed to warm to room temperature with stirring for 30 minutes. The solution was cooled to 0 C and to the solution was added aq 1M HC1 (50 mL). The mixture was stirred at room temperature overnight. The mixture was diluted with water and EtOAc and was transferred to a separatory funnel. The organic phase was isolated; washed with brine; dried over MgSC^, filtered; then concentrated in vacuo to afford 3-(trifluoromethyl)tetrahydro-2H-pyran-3-ol as a colorless oil (0.40 g, 47%). 1H-NMR (400MHz, CDC13) 5 4.01 – 3.93 (m, IH), 3.82 (dd, J=l 1.8, 2.5 Hz, IH), 3.60 (d, J=12.0 Hz, IH), 3.41 (td, J=l 1.8, 2.5 Hz, IH), 2.10 – 2.08 (m, 2H), 1.97 – 1.90 (m, IH), 1.82 (dd, J=12.9, 4.4 Hz, IH), 1.65 – 1.55 (m, IH)., 23462-75-1

As the paragraph descriping shows that 23462-75-1 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; GILLIS, Eric P.; BOWSHER, Michael S.; SCOLA, Paul Michael; WO2014/71007; (2014); 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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

2-({[2-(4-Bromo-2-hydroxyphenyl)ethyl]sulfonyl}amino)-/V-tert-butylbenzenesulfonamide (3.2 g, 6.51 mmol) and 4-(bromomethyl)tetrahydro-2/-/-pyran (3.50 g, 19.54 mmol) were added to a solution of cesium carbonate (6.36 g, 19.54 mmol) in THF (10 mL) and the reaction mixture was heated using MW at 110 C, for 2 h. The reaction mixture was diluted with NH4CI (aq) and extracted with EtOAc two times, washed with water and concentrated. Purification by chromatography on silica using gradient elution of 0-50% EtOAc in n-heptane gave 3.0 g (78 % yield) of the title compound. XH NMR (500 MHz, DMSO-c/6) delta ppm 1.06 – 1.10 (m, 9 H) 1.17 – 1.27 (m, 2 H) 1.53 (br. s., 2 H) 1.81 – 1.92 (m, 1 H) 2.91 – 2.98 (m, 2 H) 3.25 (d, 7=1.58 Hz, 2 H) 3.45 – 3.54 (m, 2 H) 3.77 – 3.85 (m, 4 H) 7.05 (d, 7=1.58 Hz, 1 H) 7.10 – 7.14 (m, 3 H) 7.32 (s, 1 H) 7.59 – 7.70 (m, 3 H) 7.89 (dd, 7=8.04, 1.10 Hz, 1 H) 8.01 (s, 1 H) 8.77 (s, 1 H); MS m/z 589, 590 [M-H]”., 125552-89-8

As the paragraph descriping shows that 125552-89-8 is playing an increasingly important role.

Reference£º
Patent; ACTURUM LIFE SCIENCE AB; SOeDERMAN, Peter; SVENSSON, Mats A; KERS, Annika; OeHBERG, Liselott; HOeGDIN, Katharina; HETTMAN, Andreas; HALLBERG, Jesper; EK, Maria; BYLUND, Johan; NORD, Johan; (0 pag.)WO2016/85392; (2016); 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.344329-76-6,Tetrahydro-2H-pyran-4-carboxamide,as a common compound, the synthetic route is as follows.

A solution of tetrahydro-2H-pyran-4-carboxamide (9.47 g, 73.3 mmol) and Lawesson’s reagent (14.83 g, 36.7 mmol) in THF (98 mL) was heated to reflux for 6 h. The reaction was cooled to room temperature, poured into saturated aqueous NaHCO3 (200 mL) and extracted with diethyl ether (4 x 100 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated. The residual solid was triturated with 1 : 1 EtOAc:hexanes (100 mL) and filtered to collect the solid. The filtrate was concentrated and re- subjected to trituration and filtration using the same conditions. The combined solids were dried under vacuum to afford tetrahydro-2A -pyran-4- carbothioamide. 4.91 g (32.1 mmol, 43.8 % yield) as a white solid 1H NMR (400 MHz, CDCb) delta ppm 7.49 (br. s., 1 H), 6.84 (br. s., 1 H), 3.94 – 4.32 (m, 2 H), 3.31 – 3.62 (m, 2 H), 2.52 – 3.03 (m, 1 H), 1.81 – 1.93 (m, 4 H)., 344329-76-6

As the paragraph descriping shows that 344329-76-6 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE LLC; ADAMS, Jerry, Leroy; FAITG, Thomas; KASPAREC, Jiri; PENG, Xin; RALPH, Jeffrey; RHEAULT, Tara Renae; WATERSON, Alex Gregory; WO2011/59610; (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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

Reference Example 1 : Tetrahvdro-pyran-4-carbonitriIe. To a solution of tetrahydro-pyran-4-one (2.0 g, 20.0 mmol) and tosyl methyl isocyanide (5.06 g, 25.9 mmol) in dimethoxyethane (15 mL) was added ethanol (1.5 niL). The reaction mixture was cooled to 0C and potassium tert-butoxide (5.57 g, 49.7 mmol) was added. The resulting reaction mixture was warmed to r.t. and stirred for Ih, then heated to 4O0C for 30 minutes. The mixture was cooled to r.t. and filtered. The resulting solid was washed with dimethoxyethane (3 x 15 mL), and the combined filtrates were evaporated to give a crude compound which was purified by column chromotography over 60-120 silica gel using 10-12% ethyl acetate in hexane to afford 5 tetrahydro-pyran-4-carbonitrile (1.05 g, 47 %) as a light yellow liquid., 29943-42-8

The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F2G LTD; WO2008/62182; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125552-89-8, 4-(Bromomethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of methyl(R)-7-(7-chloro-10-(3-(4-chloro-3,5-dimethy lphenoxy)propy 1)-6-(3,5-dimethy 1-1H-pyrazol-4-y 1)-4-methy l-l-oxo-3,4-dihydropyrazino[1,2-a]indol-2(1H)-yl)-l-methyl-1H-indole-3-carboxylate(20 mg,0. 028mmol) in DMF(0.5 mL) was added NaH(1.4 mg,0.034 mmol) and stirred for 15 min at RT.4-(Bromomethyl)tetrahydro-2H-pyran(5.5 mg,0.031 mmol) was added,and the resultingmixure was stirred overnight then concentrated in vacuo. The residue was purified by flashchromatography(Combi-flash Rf,Hex/EtOAc = 0-70% gradient) to give the title compound(20 mg,88%) as white foam LCMS: RT = 2.107 min,MS(ES) 810.3(M+H).

125552-89-8, 125552-89-8 4-(Bromomethyl)tetrahydropyran 2773286, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; VANDERBILT UNIVERSITY; LEE, Taekyu; TARR, James, C.; JEON, Kyuok; SALOVICH, James, M.; SHAW, Subrata; VEERASAMY, Nagarathanam; KIM, Kwangho; CHRISTOV, Plamen, P.; OLEJNICZAK, Edward, T.; ZHAO, Bin; FESIK, Stephen, W.; BIAN, Zhiguo; (526 pag.)WO2017/152076; (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.

To a solution of 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy)-4-(3- ((2- (2-cyclopropylphenyl) pyrrolidin-1-yl) methyl) azetidin-1-yl) benzoic acid (40 mg, 0.08 mmol) in DCM (10 mL) was added HATU (36 mg, 0.09 mmol) and TEA (86 mg, 0.85 mmol), the solution was stirred for about 0.5h, 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzenesulfonamide (27 mg, 0.170 mmol) and DMAP (12 mg, 0.09 mmol) was then added, the solution was stirred at r.t for 16h. The reaction solution was concentrated and purified by column chromatograph on silica gel (100-200 mesh, eluent: MeOH/DCM = 1/10) to give the crude product, which was purified by Pre-TLC (MeOH/DCM = 1/18) to obtain the desired compound. 1H NMR (CDCl3) delta ppm: 10.12 (s, 1H), 9.14 (s, 1H), 8.89 (s, 1H), 8.57-8.46 (m, 1H), 8.24-8.09 (m, 2H), 7.90 (d, J = 8.8Hz, 1H), 7.69 (s, 1H), 7.55-7.37 (m, 2H), 7.16-7.03 (m, 2H), 6.97-6.82 (m, 2H), 6.55 (s, 1H), 6.01 (d, J = 8.4Hz, 1H), 5.37 (s, 1H), 4.10-3.98 (m, 2H), 3.84-3.71 (m, 2H), 3.49-3.14 (m, 7H), 2.80-2.51 (m, 2H), 2.39-2.11 (m, 3H), 2.04-1.67 (m, 7H), 1.50-1.35 (m, 3H), 0.93-0.81 (m, 2H), 0.73-0.46 (m, 2H). MS (ESI, m/e) [M+1] + 805.8., 1228779-96-1

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

Reference£º
Patent; BEIGENE, LTD.; GUO, Yunhang; XUE, Hai; WANG, Zhiwei; SUN, Hanzi; (493 pag.)WO2019/210828; (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

1.48 g of a 57% oil dispersion of sodium hydride was washed with pentane to remove the oil and the sodium hydride was suspended in 10 ml of dimethylformamide. Under a nitrogen atmosphere at 1 C., the suspension was stirred while a solution of 3.00 g of 1A in 15 ml of dimethylformamide was added drop by drop. The mixture was allowed to warm to room temperature and held there for about 1.5 hours, then was cooled to 3-4 C., and a solution of 3.72 g of benzyl chloride in 5 ml of dimethylformamide was added. The mixture was stirred for one hour, then partially stripped of solvent, and the residue was held in a refrigerator overnight. Then most of the solvent was stripped and the residue was stirred in a mixture of equal volumes of water and methylene chloride. The two phases were separated; the aqueous phase was brought to pH 7 with 6 N hydrochloric acid, and extracted with methylene chloride. The organic phases were combined, washed with saturated sodium bicarbonate solution, then with saturated sodium chloride solution, dried (MgSO4) and stripped of solvent. The residue was distilled. 1 was obtained as the fraction boiling at 76 C., 0.1 Torr., 19752-84-2

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

Reference£º
Patent; Shell Oil Company; US4388104; (1983); A;,
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

EXAMPLE 29 5-(3-cyanophenyl)-5,10-dihydro-1H,3H-dipyrano[3,4-b:4,3-e]pyridine-4,6(7H,9H)-dione A mixture of tetrahydropyran-3,5-dione (Terasawa, J. Org. Chem. (1977), 42, 1163-1169) (0.27 g, 2.4 mmol), 3-cyanobenzaldehyde (0.54 g, 2.9 mmol) and the product from Example 11C (0.27 g, 2.4 mmol) in ethanol (3 mL) was heated to 80 C. for 60 hours, cooled and concentrated. The residue was purified by chromatography on silica gel (5% methanol in methylene chloride) to provide a product which was dissolved in 1:5 methanol/methylene chloride, filtered, concentrated on a steam bath to remove the methylene chloride and allowed to stand at ambient temperature for 16 hours. The resulting solid was collected by filtration, washed with methanol and dried to provide the title compound (0.062 g). mp>260; MS (ESI(+)) m/z 323 (M+H)+; MS (ESI(-)) m/z 321 (M-H)-; 1H NMR (DMSO-d6) delta 4.05 (s, 4H), 4.51 (AB q, 4H), 4.99 (s, 1H), 7.48 (m, 1H), 7.54-7.64 (m, 2H), 10.12 (bs, 1H); Anal. Calcd for C18H14N2O4: C, 67.08; H, 4.38; N, 8.69. Found: C, 66.76; H, 4.67; N, 8.56., 61363-56-2

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

Reference£º
Patent; Abbott Laboratories; US6642222; (2003); B2;,
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.1408168-76-2,Potassium trifluoro(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)borate,as a common compound, the synthetic route is as follows.

To a degassed solution of intermediate (10e) (1.35 g, 2.60 mmol) in toluene (15 ml_) and water (5 ml_) were added potassium 2-(tetrahydro-2/-/-pyran-2-yloxy)ethyltrifluoroborate (613 mg, 2.60 mmol), cesium carbonate (2.54 g, 7.79 mmol), RuPhos (121 mg, 0.26 mmol) and palladium(ll) acetate (29 mg, 0.13 mmol). The flask was sealed and the mixture was heated at 95C for 5h. The mixture was cooled to rt and water was added. The layers were separated. The aqueous layer was extracted with toluene. The combined organic layers were washed with brine, dried over Na2S04 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ AcOEt 10/0 to 5/5) to provide intermediate (1 1 a) (1 .21 g, 2.12 mmol, 81%) as a yellow oil. MS m/z ([M+Na]+) 591., 1408168-76-2

The synthetic route of 1408168-76-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MUTABILIS; BARBION, Julien; CARAVANO, Audrey; CHASSET, Sophie; CHEVREUIL, Francis; LE STRAT, Frederic; SIMON, Christophe; BRIAS, Julie; LEBEL, Remi; (80 pag.)WO2020/25543; (2020); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125552-89-8, 4-(Bromomethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 1H-indazole-5-sulfonic acid (2-chloromethyl-3-hydroxypropyl)(4-ethylphenyl)amide (1.26 g; 0.64 mmol), cesium carbonate (0.31 mg; 0.96 mmol) and 4-(bromomethyl)tetrahydropyran (100 mul; 0.76 mmol) in N-methyl-2-pyrrolidone (4 ml) is stirred for 1 hour at a temperature of 80 C. The reaction medium is diluted with ethyl acetate (20 ml). The organic phase is washed with saturated NH4Cl solution, with saturated NaHCO3 solution and with water. The organic phase is dried (MgSO4), filtered and concentrated. The crude product is purified by preparative HPLC (C18 column, eluent: acetonitrile in water/0.1% of formic acid). The 1-(tetrahydropyran-4-ylmethyl)-1H-indazole-5-sulfonic acid (3-chloro-2-hydroxymethylpropyl)(4-ethylphenyl)amide (100 mg; 31%) is obtained in the form of a colorless oil. 1H NMR (DMSO-d6) delta: 1.18 (t, J=7.6 Hz, 3H), 1.25-1.43 (m, 4H), 1.73 (p, J=6.4 Hz, 1H), 2.61 (q, J=7.6 Hz, 2H), 3.23 (td, J=11.3, 3.0 Hz, 2H), 3.35-3.41 (m, 1H), 3.46-3.52 (m, 1H), 3.52-3.63 (m, 2H), 3.69 (qd, J=10.8, 4.9 Hz, 2H), 3.82 (ddd, J=11.4, 4.3, 2.2 Hz, 2H), 4.39 (d, J=7.0 Hz, 2H), 4.69 (t, J=5.1 Hz, 1H), 6.95-7.02 (m, 2H), 7.16-7.22 (m, 2H), 7.44 (dd, J=9.0, 1.8 Hz, 1H), 7.92 (d, J=8.9 Hz, 1H), 8.10 (d, J=1.6 Hz, 1H), 8.31 (s, 1H). MS: [M+H]=506, 125552-89-8

The synthetic route of 125552-89-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GALDERMA RESEARCH & DEVELOPMENT; MUSICKI, Branislav; OUVRY, Gilles; THOREAU, Etienne; BOUIX-PETER, Claire; (85 pag.)US2017/342062; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics