Tag: M.W:200-300

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

A mixture of sodium hydride (60 wt.% in mineral oil, 15.74 mg) in DMF (0.7 mL) was added to a solution of tert-butyl 2-chloro-5-(5-chloro-2-fluoropyridin-4-yl)phenylcarbamate (213 mg, 0.596 mmol) in DMF (0.70 mL) at 0 C. The resulting mixture was stirred at 0 C for 30 min. To this stirred mixture was then added (tetrahydro-2H-pyran-4-yl)methyl 4- methylbenzenesulfonate (161 mg, 0.596 mmol) in one portion. The mixture was warmed to 40 C and maintained at this temperature for 16 hrs. The reaction mixture was diluted with EtOAc, washed with IN aqueous sodium hydroxide solution, water and brine, dried over sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by preparative TLC [silica gel, 1 mm; EtO Ac/heptane = 15/85] providing [2-chloro-5-(5-chloro-2-fluoro- pyridin-4-yl)-phenyl]-(tetrahydro-pyran-4-ylmethyl)-carbamic acid tert-butyl ester (176 mg) as a colorless oil. LCMS (m/z): 355.0/356.9 [M+H, loss of t-Bu]; Retention time = 1.21 min., 101691-65-0

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

Reference£º
Patent; NOVARTIS AG; ANTONIOS-MCCREA, William R.; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; MARTIN, Eric J.; PAN, Yue; PFISTER, Keith B.; SENDZIK, Martin; SUTTON, James; WAN, Lifeng; WO2012/66065; (2012); 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.1240390-36-6,tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

10517] A 50-mE 1-neck round bottom flask was charged with reactant 22-A (0.50 g, 2.31 mmol), 6-8 (0.80 g, 2.31 mmol) and NaHCO3 (0.39 g, 4.6 mmol) in ethanol (10 ml) and water (10 ml). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated down, re-dissolved in EtOAc (100 mE), washed with water (2x) and dried over Na2504. After concentration, the crude was dissolved in 4N HC1/Dioxane (11 ml) and stirred atroom temperature for 3 hours to dc-Hoc. The reaction mixture was concentrated down again. The residue and DRU (1.58 g, 10.4 mmol) were dissolved in EtOH (10 mE). Heated to 50 C. for 20 minutes. Afier concentration, the crude was purified by column chromatography on silica gel with hexane-EtOAc to obtain 22-C. ECMS-ESI (mlz): [M+H]. found: 399., 1240390-36-6

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 fields.

Reference£º
Patent; Gilead Sciences, Inc.; Bacon, Elizabeth M.; Cai, Zhenhong R.; Cottell, Jeromy J.; Ji, Mingzhe; Jin, Haolun; Lazerwith, Scott E.; Morganelli, Philip Anthony; Pyun, Hyung-jung; (101 pag.)US2016/176870; (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.53911-68-5,4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Prepared by refluxing an equimolar mixture of 3-(4-chlorophenyl)glutaric anhydride and commercial 4-chloro-2-hydroxyaniline in dichloromethane for 0.5 h. After cooling to rt the precipitated product is isolated by suction filtration, washed, and dried to provide 90% of N-(2-hydroxy-4-chlorophenyl)-3-(4-chlorophenyl)glutaramic acid as light red crystals. 2, 53911-68-5

53911-68-5 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione 104639, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); 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.1152567-60-6,4-(4-Bromophenyl)tetrahydro-2H-pyran-4-carboxylic acid,as a common compound, the synthetic route is as follows.

Example 82 O4-[4-((E)-2-Cyano-ethenesulfonyl)-phenyl]-tetrahydro-pyran-4-carboxylic acidTo a solution of l-(4-bromophenyl)tetrahydro-2H-pyran-4-carboxylic acid (2.85 g, 10 mmol) in anhydrous THF (100 ml) under nitrogen at – 80 C (ether/dry ice), was added slowly Phenyl lithium in toluene 1.8 M (7 mL, 12.5 mmol). After 5 min, to this mixture, n- BuLi (2.5 M in hexane) (5.2 mL, 13 mmol) was added. A cloudy suspension was slowly formed. Twenty minutes after BuLi addition, a stream of sulfur dioxide was bubbled through the mixture for 15 min. The reaction mixture was then allowed to warm up to room temperature and the solvent was removed in vacuo. The sulfmate residue was dissolved in water (15 ml), acetic acid (8 ml), and MeOH (20 ml), followed by addition of 2-chloroacrylonitrile (1.3 g, 15 mmol). The resulting mixture was stirred at room temperature overnight. The organic solvents were removed and the residue was diluted with 20 ml of water. The solution was adjusted to pH5-6 with sat. K2HP04 aq. solution, then extracted with dichloromethane (2×50 ml), dried over MgS04. After filtration, the filtrate was stirred with triethylamine (2.8 mL, 20 mmol) for 1 h. The solution was washed with 10% aq citric acid and brine, dried over MgS04. The final product was purified by flash column chromatography (silica gel, dichloromethane/Ethyl acetate, gradient) to give 4-[4-((E)-2-Cyano-ethenesulfonyl)-phenyl]-tetrahydro-pyran-4- carboxylic acid (0.87 g, 27%) as a white solid. LCMS (ESI): m/z = 276 (M-C02H)+; 1H- NMR (DMSO-d6, 400 MHz) delta 13.00 (s, 1H), 8.23 (d, 1H, J = 15.7 Hz), 7.91 (d, 2H, J = 8.7 Hz), 7.74 (d, 2H, J = 8.7 Hz), 6.92 (d, 1H, J = 15.7 Hz), 3.82 (m, 2H), 3.48 (m, 2H), 2.40 (m, 2H), 1.88 (m, 2H); 13C-NMR (DMSO-d6, 100 MHz) delta 174.3, 150.2, 149.0, 136.1, 128.4, 127.6, 114.6, 112.2, 64.6, 48.5, 33.7., 1152567-60-6

1152567-60-6 4-(4-Bromophenyl)tetrahydro-2H-pyran-4-carboxylic acid 43119054, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; CEPHALON, INC.; UNIVERSITY OF HAWAII; UNIVERSITY OF UTAH RESEARCH FOUNDATION; DORSEY, Bruce; KUWADA, Scott K.; THEROFF, Jay P.; ZIFICSAK, Craig A.; WO2012/116151; (2012); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

101691-94-5, 4-(Iodomethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Under argon, 1.66 ml of 1,1,1,3,3,3-hexamethyldisilazane are dissolved in 20 ml of tetrahydrofuran. With ice cooling, 2.90 ml of n-butyllithium (2.5 M in n-hexane) are added dropwise, and the mixture is stirred at 0 C. for another 30 minutes. At -78 C., this solution is then added dropwise to a stirred solution of 2.0 g of ethyl (10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)acetate in 100 ml of tetrahydrofuran. The reaction mixture is stirred at -78 C. for 20 minutes, and 2.0 g of 4-(iodomethyl)tetrahydro-2H-pyran are then added dropwise. The cooling bath is removed and the mixture is allowed to slowly warm to room temperature. The reaction mixture is stirred at room temperature overnight. 10 ml of water are then added, the tetrahydrofuran is removed under reduced pressure and the residue is extracted three times with in each case 100 ml of ethyl acetate. The combined organic phases are dried over MgSO4 and then concentrated under reduced pressure. The residue is purified on silica gel using the mobile phase n-heptane:ethyl acetate (100%:0%)=>n-heptane:ethyl acetate (0%:100%). This gives 2.0 g of ethyl 2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)-3-(tetrahydropyran-4-yl)propionate as a colorless solid. C23H27NO5S (429.54), LCMS (ESI): 430.2 (M+H+).

101691-94-5, 101691-94-5 4-(Iodomethyl)tetrahydro-2H-pyran 2795507, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; SANOFI-AVENTIS; US2009/325942; (2009); 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.

Example 11; N-Cyclopropyl-3-[N-(2,2-dimethyl-1-oxoindan-5-yl)-N-(3-hydroxypropyl)amino]-4-methylbenzamidea) N-Cyclopropyl-3-[N-(2,2-dimethyl-1-oxoindan-5-yl)-N-(3-(tetrahydropyran-2-yloxy)propyl)amino]-4-methylbenzamideTo a suspension of N-cyclopropyl-3-(2,2-dimethyl-1-oxoindan-5-ylamino)-4-methylbenzamide (0.2 g, 0.57 mmol, obtained in example 2) in dry toluene (6.5 mL), sodium hydride (50 mg, 60% dispersion in oil, 1.14 mmol) and 15-crown-5 (4 mg, 0.02 mmol) were added under argon and the mixture was stirred at room temperature for 20 min. Then, 3-bromopropanol tetrahydropyranyl ether (0.13 g, 0.57 mmol) was added and the mixture was heated at 90 C. overnight. It was allowed to cool and diluted with EtOAc and saturated NaHCO3. The phases were separated and the organic phase was dried over Na2SO4. The solvent was evaporated to afford the desired compound (quantitative yield).LC-MS (method 1): tR=9.74 min; m/z=491.2 [M+H]+.

33821-94-2, The synthetic route of 33821-94-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PALAU PHARMA, S.A.; US2010/222363; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

31608-22-7, 2-(4-Bromobutoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

PREPARATION 10 7-tetrahydropyranyloxyhept-2-yne-1-ol (Formula XXII: A is trimethylene). Lithium metal (7.7 g.) is added in small pieces with stirring to a solution of ferric nitrate (300 mg.) in 1 l. of liquid ammonia. The mixture is then stirred under reflux until the blue color is replaced by a pale grey color. Then, a solution of propargyl alcohol (28 g.) in 250 ml. of diethyl ether is added slowly with stirring. After stirring 2 hours under reflux, a solution of 1-tetrahydropyranyloxy-4-bromobutane (118 g.) in 250 ml. of diethyl ether is added slowly with stirring. After stirring 4 hours under reflux, 300 ml. of water and then 300 ml. of diethyl ether are added. The mixture is stirred about 15 hours, the ammonia being allowed to evaporate during that time. The diethyl ether layer is separated, washed with water and with saturated aqueous sodium chloride solution, dried, and evaporated under reduced pressure to give a residue. The residue is chromatographed on 4 kg. of silica gel, eluding with 8 l. 20%, 6 l. 40%, 6 l. 60%, 6 l. 80%, and 9 l. 100% ethyl acetate-Skellysolve B mixtures, collecting 1.5 l. fractions. Fractions 9-12 are combined and evaporated to give 56 g. of 7-tetrahydropyranyloxyhept-2-yne-1-ol., 31608-22-7

As the paragraph descriping shows that 31608-22-7 is playing an increasingly important role.

Reference£º
Patent; The Upjohn Company; US3983155; (1976); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

101691-94-5, 4-(Iodomethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation 8: Triphenyl(tetrahydropyran4-ylmethyl)phosphonium iodide; PPh,iA mixture of Preparation 7 (350g5 1.55M) and triphenylphosphine (406g, 1.55M) in acetonitrile (1.6L) was heated under reflux. After 27h the mixture was cooled and filtered, washed with diethyl ether and dried in air to provide a white solid (504g). Filtrate and washings were returned to reflux and concentrated to 750mL, reflux was maintained for 16h before cooling and dilution with diethyl ether (ca 1,2L). A precipitate formed which was stirred for 30min before being filtered, washed with diethyl ether (2 x 300mL) and dried in air to yield a further crop (lOOg). Overall yield of the title compound (604 g, 80%). RT = 2.7min; m/z (ES+) = 361.2.

101691-94-5, The synthetic route of 101691-94-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PROSIDION LIMITED; WO2006/16178; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

53911-68-5, 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

53911-68-5, A solution of triethyl amine (1.5 ml) in 1,4-dioxane (5 ml) was added to a mixture of commercial 4- phenoxyaniline (1.85 g) and 3-(4-chlorophenyl)glutaric anhydride. The resulting solution was stirred at rt for 0.5 h and at 400C for 2 h. Under cooling with ice cone. HCI (2 ml) and water (10 ml) was added. A gummy precipitate is formed from which the aqueous layer is removed by decantation. Crystallisation was induced by heating with methanol (5 ml). After cooling in the refrigerator the precipitate was isolated by filtration, washed with methanol and diethyl ether, and dried in vacuo to give colourless, powdery crystals (3 g) of /V-(4-phenoxyphenyl)-3-(4-chlorophenyl)- glutaramic acid.

53911-68-5 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione 104639, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; UNIVERSITAET DES SAARLANDES; ENGEL, Matthias; FROeHNER, Wolfgang; STROBA, Adriane; BIONDI, Ricardo M.; WO2010/43711; (2010); A1;,
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

Step 3 {(3R,4R)-4-[7-(6-Ethyl-pyridin-2-ylcarbamoyl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester To a solution of 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (6-ethyl-pyridin-2-yl)-amide (0.060 g, 0.19 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (0.081 g, 0.38 mmol) in dioxane (3 mL) was added DIPEA (0.099 mL, 0.57 mmol). The reaction mixture was heated at 110 C. overnight. The reaction mixture was cooled then diluted with EtOAc, washed with aqueous sodium carbonate, then brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue obtained was then purified by chromatography (silica, 40 g, 10 to 60% EtOAc in hexanes) to give {(3R,4R)-4-[7-(6-ethyl-pyridin-2-ylcarbamoyl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (0.040 g, 0.080 mmol, 42.6%) as a white solid. LCMS m/z [M+H]=499., 1240390-36-6

The synthetic route of 1240390-36-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Hoffmann-La Roche Inc.; Chen, Shaoqing; Hermann, Johannes Cornelius; Le, Nam T.; Lucas, Matthew C.; Padilla, Fernando; US2013/178460; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics