Category: 101691-65-0

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.101691-65-0,(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

Step B: 1-(Tetrahydropyran-4-yl)methyl-7-chloro-1H-indole-3-carboxylic acid To a solution of 7-chloro-1H-indole-3-carboxylic acid (7.5 g, 38.0 mmol) in dimethylformamide (100 ml) at 10 C. under nitrogen was added sodium hydride (60% dispersion in mineral oil, 3.1 g, 76.0 mmol) portionwise over 10 mins, maintaining the temperature below 15 C. The cooling bath was removed and the suspension stirred for 90 mins. Toluene-4-sulfonic acid tetrahydopyran-4-ylmethylester (14.6 g, 53.0 mmol) was added. The mixture was heated at 50 C. with stirring for 6 h. Dimethylformamide was removed by evaporation and the residue was dissolved in water (500 ml). The emulsion was washed with dichloromethane (2*100 ml). The aqueous phase was acidified to pH 1 using 5 M hydrochloric acid and the precipitate filtered off, washed with water to neutrality and dried to afford 1-(tetrahydropyran-4-yl)methyl-7-chloro-1H-indole-3-carboxylic acid (15.0 g, 51.0 mmol) as a white solid., 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; AKZO NOBLE N.V.; US2007/82931; (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.101691-65-0,(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

The quantity of reagents and materials used in the following procedure were based on the quantity of N-(l-Methyl-l-phenylethyl)-lH-indazole-3-carboxamide obtained in the preceding step, as indicated. A solution of N-(l -methyl- l-phenylethyl)-lH-indazole-3-carboxamide (1.0 molar eq.) in anhydrous DMF (5 volumes) was mixed with anhydrous potassium carbonate (5.84 molar eq.). (Tetrahydro-2H-pyran-4-yl) methyl 4-methylbenzenesulfonate (1 molar eq.) was added portion wise over a period of 5 minutes at ambient temperature to the reaction mixture. The resulting reaction mixture was heated to 70C for at least 15 hours using an oil bath. The reaction mixture was evaporated at a 40C bath temperature under reduced pressure to remove the DMF. The evaporated residue was mixed with ethyl acetate (5 volumes) and then poured into ice (5 weight equivalents). The mixture was stirred until the ice melted. The bilayer was separated and the aqueous layer extracted with ethyl acetate (4 x 3 volumes). The combined extracts were washed with 50% saturated sodium carbonate solution (4 x 1 volume), then dried over sodium sulfate and filtered. The filtrate was evaporated at a 40 bath temperature and co-evaporated with ethyl acetate (3 x 2.5 volumes). The resultant residue was redissolved and hot ethyl acetate (4 volumes) and filtered through 60 angstrom silica (2.5 volumes) topped with a layer of anhydrous sodium sulphate. The filter bed was washed with hot ethyl acetate (2 volumes per fraction) until all of the product was released. Product containing fractions were evaporated with a bath temperature of 40C. The crude product was triturated with methyl tert-butyl ether (MTBE)(2 volumes) at room temperature of the 2 hours, and then in an ice bath for one hour. The suspension was filtered, then rinsed with cold MTBE (4 x 1 volume). The resulting white solid was then dried under vacuum to constant weight, mp 112.7 ¡À 0.5 . IR vmax/cm_1 3328, 1664 (amide). lU NMR (400 MHz, DMSO-d6) delta 8.03 (1H, d, HI), 7.97 (1H, s, H5), 7.82 (1H, d, H4), 7.41-7.44 (3H, m, H2, H3), 7.33 (2H, dt, H8), 7.20 (2H, dd, H7), 4.41 (2H, d, H10), 3.84 (2H, d, H13), 3.25 (2H, m, H14), 2.23 (1H, m, H15), 1.74 (6H , s, H6), and 1.39 (4H, m, Hl l, H12). MS (ESI+) m/z 378 (MH+). Anal. Calcd for C23H27N3O2: C, 73.18; H, 7.21; N, 11.13. Found: C, 73.44; H, 7.22; N, 11.23. 1 13 H and i3C NMR scans for SGT-42 are provided in Figures 1 and 2, respectivley., 101691-65-0

As the paragraph descriping shows that 101691-65-0 is playing an increasingly important role.

Reference£º
Patent; BOWDEN, Matthew James; WILLIAMSON, James Peter Bernard; WO2014/167530; (2014); 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

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

Step 2 [0340] (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate obtained in Step 1 (1.20 g, 4.44 mmol) was dissolved in acetone (15 mL), sodium iodide (2.00 g, 13.3 mmol) was added thereto, and under reflux with heating, the mixture was stirred for 4 hours. After cooling the reaction mixture to room temperature, the precipitated solid was removed by filtration, and the filtrate was evaporated under reduced pressure. Chloroform was added to the residue, and the precipitated solid was removed by filtration. The filtrate was concentrated under reduced pressure, whereby 4-(iodomethyl)tetrahydro-2H-pyran (0.946 g, 94%) was obtained. 1H NMR (300 MHz, CDCl3, delta): 3.99-3.96 (m, 2H), 3.37 (td, J = 11.7, 2.1 Hz, 2H), 3.10 (d, J = 6.6 Hz, 2H), 1.81-1.65 (m, 3H), 1.37-1.24 (m, 2H)., 101691-65-0

As the paragraph descriping shows that 101691-65-0 is playing an increasingly important role.

Reference£º
Patent; Kyowa Hakko Kirin Co., Ltd.; FURUTA, Takayuki; SAWADA, Takashi; DANJO, Tomohiro; NAKAJIMA, Takahiro; UESAKA, Noriaki; EP2881394; (2015); 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

Prepared as described by adaptation of the following literature reference: Watson, R.J. et al. Tetrahedron Lett. 2002, 43, 683-685. To 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 suspension is stirred at 70 C for 4.5 h. The reaction mixture is cooled to RT and water (1 .8 L) is added. The organic layer is washed with 10% aq. K2C03 solution (1.8 L) and water (1 L). The organic layer is filtered through Celite (20 g), activated charcoal (20 g) and Na2S04 (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. Yield: 96%; ESI-MS: 175 [M+H]+

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; BINDER, Florian; DOODS, Henri; MUELLER, Stephan, Georg; NICHOLSON, Janet, Rachel; SAUER, Achim; WO2014/184327; (2014); 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

A solution of 5-bromo-2-chloropyridin-3-amine (1 .3 g, 6.27 mmol) in DMF (20 mL) was added slowly sodium hydride (60 wt.% in mineral oil, 0.301 g) was stirred for 20 min, followed by addition of (tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate (1.694 g, 6.27 mmol). The resulting reaction mixture was stirred at room temperature for 58 hrs, diluted with EtOAc, washed with water, brine, dried over sodium sulphate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, EtOAc/hexane = 22/78) providing 5-bromo-2-chloro-N-((tetrahydro-2H-pyran-4- yl)methyl)pyridin-3-amine (1 .27 g). LCMS (m/z): 305.0 [M+H]+; Rt = 0.89 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; BARSANTI, Paul, A.; HU, Cheng; JIN, Xianming; NG, Simon, C.; PFISTER, Keith, B.; SENDZIK, Martin; SUTTON, James; WO2012/101064; (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.101691-65-0,(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

2-(6-(1 ,4-Diazepan-1-yl)-2-(4-fluoro-3-methoxyphenyl)-4-oxoquinazolin-3(4/-/)-yl)-lambda/- isopropylacetamide (EXAMPLE 1 i) (30 mg, 0.064 mmol), (tetrahydro-2/-/-pyran-4-yl)methyl 4-methylbenzenesulfonate (35 mg, 0.128 mmol) and DIPEA (17 mg, 21 mul, 0.128 mmol) were dissolved in DMF (1 ml_) and stirred at room temperature overnight. Purification by preparative HPLC afforded 2-{2-(4-fluoro-3-methoxyphenyl)-4-oxo-6-[4-(tetrahydropyran-4- ylmethy^perhydro-IA-diazepin-i-ylJ^H-quinazolin-S-ylj-N-isopropylacetamide (EXAMPLE 11a) (5 mg, 0.0088 mmol, 14%).Data for 2-{2-(4-fluoro-3-methoxyphenyl)-4-oxo-6-[4-(tetrahydropyran-4-ylmethyl) perhydro- 1,4-diazepin-1-yl]-4H-quinazolin-3-yl}-N-isopropylacetamide (EXAMPLE 11a): MS (ESI) m/z:, 101691-65-0

As the paragraph descriping shows that 101691-65-0 is playing an increasingly important role.

Reference£º
Patent; N.V. ORGANON; WO2008/33764; (2008); A2;,
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

A mixture of Example 203A (1.9 g, 7.0 mmol), 2-amino-5-methylthiazole (0.80 g, 7.0 mmol) and tetrabutylammonium iodide (1.3 g, 3.5 mmol) in 3 mL of N,N- dimethylformamide was warmed to 85 0C and was allowed to stir for 24 hours. The mixture was diluted with 10 mL OfCH2Cl2, washed with 10% aqueous NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 10% methanol in ethyl acetate then 9:1 :0.1 CH2Cl2 : methanol : NH4OH) afforded the title compound. MS (DCI/NH3) m/z 213 (M+H)+, 101691-65-0

Big data shows that 101691-65-0 is playing an increasingly important role.

Reference£º
Patent; ABBOTT LABORATORIES; WO2009/67613; (2009); 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

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

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

CsC03 (313 mg, 0.961 mmol) was added to a solution of ethyl 2-((3-(4-((2′- chloro-4′-hydroxy-[1 ,1 ‘-biphenyl]-3-yl)methoxy)phenyl)oxetan-3-yl)oxy)propanoate (357 mg, 0.739 mmol) in DMF (5 mL) and the reaction mixture was stirred at RT for 10 minutes followed by the addition of (tetrahydro-2H-pyran-4-yl)methyl 4- methylbenzenesulfonate (commercial sources, 200 mg, 0.739 mmol). The reaction mixture was heated at 80 C for 2 hours. After completion of reaction the reaction mixture was quenched with ice-cold water and concentrated. The residue was dissolved in ethylacetate and washed with water. The organic layer was dried over anhydrous sodium sulphate, concentrated and purified by flash chromatography to obtain the title compound as semi solid (266 mg). Yield: 61.93%; 1H NMR (CDCI3, 300 MHz): delta 7.48 (s, 1H), 7.45-7.41 (m, 3H), 7.32-7.24 (m, 3H), 7.02-6.99 (m, 3H), 6.88-6.84 (m, 1H), 5.13 (s, 2H), 5.04 (d, J = 6.6 Hz, 1H), 4.95-4.86 (m, 3H), 4.06- 4.05 (m, 2H), 4.01-3.94 (m, 2H), 3.85-3.77 (m, 3H), 3.50-3.42 (m, 2H), 2.07-2.09 (m, 1H), 1.79-1.75 (m, 2H), 1.50-1.46 (m, 2H),1.32 (d, J= 6.9 Hz, 3H), 1.16 (t, J= 7.2 Hz, 3H); MS (m/z) 603.2 [M+ Na]., 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; PIRAMAL ENTERPRISES LIMITED; SHARMA, Rajiv; HALDER, Somnath; KUMAR, Sanjay; WO2014/170842; (2014); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics