Heterocyclic Building Blocks-Tetrahydropyrans

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

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,101691-65-0

Step 3: Synthesis of Thioacetic acid S-(tetrahydro-pyran-4-ylmethyl)ester; Prepared as described by adaptation of the following literature reference:Watson, R. J. et al. Tetrahedron Lett. 2002, 43, 683-685.To a solution of 224 g (0.83 mol) of toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester in methyl isobutylketone (1.6 L) are added 189 g (1.66 mol) of potassium thioacetate. The beige suspension is stirred at 70 C. for 4.5 h. The reaction mixture is cooled to room temperature and water (1.8 L) is added. The organic layer is washed with 10% aqueous K2CO3 solution (1.8 L) and water (1 L). The organic layer is filtered through celite (20 g), activated charcoal (20 g) and Na2SO4 (20 g) and the filtrate is concentrated under reduced pressure. The residual oil is azeotroped with methylcyclohexane (200 mL) and n-heptanes (250 mL) to afford 138 g of thioacetic acid S-(tetrahydro-pyran-4-ylmethyl)ester as a yellow-orange oil (CAUTION: Stench.). Yield: 96%; ES-MS: m/z 175 [M+H]; 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.23-1.40 (2H, m), 1.59-1.78 (3H, m), 2.33 (3H, d, J=4.16 Hz), 2.82 (2H, dd, J=6.24, 3.79 Hz), 3.27-3.39 (2H, m), 3.88-4.02 (2H, m)

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

Reference£º
Patent; Boehringer Ingelheim International GmbH; US2010/76029; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

220641-87-2, N-Methyltetrahydro-2H-pyran-4-amine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step C:; A 25 mL round bottom flask were charged with 86-3 (0.022 g, 0.038 mmol), methylene chloride (2 mL), N-methyl-N-tetrahydro-2H-pyran-4-ylamine (0.009 g, 0.56 mmol), sodium triacetoxyborohydride (0.032 g, 0.15 mmol), molecular sieves (20 mg) and triethyl amine (0.019 g, 0.188 mmol). The mixture was stirred at room temperature for 12 hours. The reaction mixture was quenched with MeOH and stirred for 20 minutes, then filtered and concentrated. The resulting residue was purified by RP HPLC (YMC column, 20% to 80% acetonitrile in water) to afford product 86-4 as a TFA salt (m/z (ES) (M+H)+= 683)., 220641-87-2

The synthetic route of 220641-87-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK & CO., INC.; WO2007/41052; (2007); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

23462-75-1, Dihydro-2H-pyran-3(4H)-one (4.00 g, 40.0 mmol) was dissolved in THF (32.0 mL) and chlorotrimethylsilane (12.8 mL, 100 mmol) was added. The reaction was stirred at room temperature for 10 minutes. Triethylamine (15.0 mL, 108 mmol) was then added dropwise under nitrogen. A white precipitate formed and the resulting suspension was heated to 70C over the weekend. The reaction mixture was cooled to room temperature and concentrated in vacuo. Pentane (80 mL) was added, the suspension was filtered, and the solid was washed with pentane (40 mL). The filtrate was concentrated in vacuo to give the title compound as a liquid that was used as is in the next step without further purification. 1H NMR (500 MHz, CDCI3) delta 4.98-4.92 (m, 1H), 3.88 (m, 2H), 3.69 (t, / = 5.5 Hz, 2H), 2.16 (m, 2H), 0.19 (s, 9H).

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

Reference£º
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; MARTINEZ, Michelle; FALCONE, Danielle; TORRES, Luis; DENG, Yongqi; KURUKLASURIYA, Ravi; ZENG, Hongbo; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146491; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics