Tag: M.W:200-300

223734-62-1, 2-((S)-Dec-1-yn-5-yloxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: Preparation of chiral benzyl alkynol (3).; Table 2Triethylamine 101.19 0.68 g 0.0068Toluene NA 10 ml NAProcedure: A 50-mL, two-necked, round-bottomed flask equipped with a magnetic stirrer and stir bar was charged with zinc triflate (3.17 g, 0.0087 mol) and (+)-N-methylephedrine (1.22 g, 0.0068 mol) in toluene (5 mL). To this mixture triethylamine was added (0.68 g, 0.0068 mol) and this gelatinous mixture was stirred at ambient temperature for 1 -2 h. To this mixture was then added a solution of alkyne (1.57 g, 0.0065 mol) in toluene (4 mL), stirred at ambient temperature for 15-30 minutes followed by addition of a solution of aldehyde (2) (0.50 g, 0.0026 mol in 1-2 mL toluene). Progress of the reaction was monitored by TLC (Note 1). After stirring the mixture at room temperature for 16 h, TLC indicated completion of reaction. The reaction mixture was quenched by slow addition of water (10 mL). This was stirred for 5-10 minutes and organic layer containing desired compound was separated. The aqueous layer was extracted with ethyl acetate (10 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo to obtain a crude product. The crude product wa~ purified by column chromatography using 250-400 mesh silica gel. A solvent gradient of ethyl acetate in hexanes (5-20%) was used to elute the product from the column. All fractions containing the desired pure product were combined and concentrated in vacuo to give pure chiral benzyl alkynol (3, 700 mg, -70%). The structure was consistent with spectral data.1H NMR (CDC13, 300 MHz) delta 0.84 (t, 3H, J = 6 Hz), 1.25 – 1.82 (m, 17H), 2.28 (t, 1H, J = 6 Hz), 2.34 -2-42 (m, 2H), 3.42 -3.52 (m, 1H), 3.61 – 3.74 (m, 3H), 3.78 (s, 3H), 3.81 -3.95 (m, 1H), 4.61 (s, 2H), 4.68 (m, 1H), 4.94 – 5.01 (m, 2H), 5.62 (br s, 1H), 5.97 – 6.07 (m, 1H), 6.76 (d, 1H, J= 8 Hz), 7.16 -7.27 (m, 1H), 7.38 -7.43 (m, 1H); 13C NMR (CDC13, 75 MHz) 84.75, -4.38, -3.49, 14.12, 14.16, 14.84, 15.52, 18.06, 18.38, 20.04, 20.24, 22.70, 24.76, 25.25, 25.56, 25.72, 25.94, 29.67, 31.22, 31.28, 32.05, 32.11, 32.65, 33.41, 34.01 , 35.08, 52.22, 62.36, 62.84, 63.09, 66.04, 75.41, 76.44, 76.68, 80.83, 81.22, 85.57, 86.01, 97.31, 98.85, 110.89, 1 14.80, 119.77,1 19.82, 125.56, 127.11, 127.16, 136.46, 136.52, 142.66, 142.73, 155.83, 169.68; MS: (M+Na) 495.6.Note 1 : Completion of the reaction was monitored by thin layer chromatography (TLC) using a thin layer silica gel plate; eluent: 20% ethyl acetate in hexanes., 223734-62-1

As the paragraph descriping shows that 223734-62-1 is playing an increasingly important role.

Reference£º
Patent; UNITED THERAPEUTICS CORPORATION; BATRA, Hitesh; PENMASTA, Raju; SHARMA, Vijay; TULADHAR, Sudersan M.; WALSH, David A.; WO2011/153363; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

693287-79-5, tert-Butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

693287-79-5, To a solution of tetrahydropyran-4-one (71.6 g, 715 mmol) in methanol (2 L) was added tert-butylcarbazate (100 g, 758 mmol) at ambient temp. The mixture was stirred at ambient temp for 20 h. The reaction mixture was concentrated under reduced pressure to dryness to afford a white solid (154 g). To a suspension of the white solid (154 g, 715 mmol) in water (1 L) was added acetic acid (500 mL, 8.73 mol) and the mixture was stirred for 30 min to get a clear solution. To this solution, solid NaCNBH3 (44.5 g, 708 mmol) was added portion-wise. The mixture was stirred at ambient temp for 2 h. The mixture was then transferred to a 12 L flask, cooled to 0 C., and quenched with 1N NaOH (8.73 L, 8.73 mol). The mixture was extracted with CH2Cl2 (3¡Á3 L) and dried over Na2SO4. The organic layer was filtered and concentrated to afford a white solid (164 g, contains 15% of N-acetyl-N’-Boc-hydrazine derivative). Chromatography [silica, ethyl acetate/MeOH (95:5] gave 94 g of 90% pure boc-hydrazine. A solution of boc-hydrazine (50 g, 231 mmol) in methanol (500 mL) was added a solution of HCl in dioxane (462 mL, 1.85 mol, 4.0 M). The mixture was stirred at ambient temp overnight. Concentration of the reaction mixture under reduced pressure afforded the title compound as a white solid (43 g, 98%). 400 MHz 1H NMR (DMSO) delta 3.85-3.82 (m, 2H), 3.27-3.21 (m, 2H), 3.13-3.05 (m, 1H), 1.88-1.84 (m, 2H), 1.48-1.38 (m, 2H). MS: (M+H m/z=117.2).

The synthetic route of 693287-79-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Pfizer Inc; US2009/30003; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

141095-78-5, 2-Bromo-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 a mixture of 2-mercapto-4,6-dimethylnicotinonitrile (50 mg, 0.30 mmol, 1 equivalent) in isopropyl alcohol (2 mL) was added 2-bromo-l-(tetrahydro-2H-pyran-4-yl)ethan- 1-one (0.045 mL, 0.37 mmol, 1.2 equivalent) and 10% potassium hydroxide (0.28 mL). After 10 minutes, the reaction was concentrated in vacuo. Purification by reverse phase HPLC afforded 32 mg (37%) of the title compound. 1H NMR (400 MHz, OMSO-d6) delta 7.76 (s, 2H), 7.08 (s, 1H), 3.92 (d, J= 11.1 Hz, 2H), 3.45 (ddd, J= 11.0, 11.2, 3.0 Hz, 2H), 2.97-2.91 (m, 1H), 2.72 (s, 3H), 2.52 (s, 3H), 1.72-1.66 (m, 4H); ES-MS [M+l]+: 291.2., 141095-78-5

The synthetic route of 141095-78-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig W.; ENGERS, Darren W.; CONN, P. Jeffrey; BOLLINGER, Katrina A.; CAPSTICK, Rory; SPEARING, Paul; BOLLINGER, Sean R.; (72 pag.)WO2018/85808; (2018); 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.693287-79-5,tert-Butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate,as a common compound, the synthetic route is as follows.

693287-79-5, Example 63 Synthesis of 3-Ethyl-6-fluoro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine A mixture of tert-butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate (3.8 g, 0.018 mol) and trifluoroacetic acid (20 mL, 0.3 mol) were stirred in dichloromethane (20 mL) for 90 minutes. The mixture was concentrated, and the residue was taken up in acetonitrile (30 mL). 1-(2,6-difluoropyridin-3-yl)propan-1-one (2.34 g, 0.0137 mol, prepared as described above in Example 62) was then added, and the resulting mixture was stirred at 75 C. for 72 hr. After cooling to room temperature, the mixture was concentrated, and the residue was purified by flash chromatography on silica gel using a 10-50% hexane:ethyl acetate gradient (flow rate 20 mL/min). The organics were combined and the crude product was then extracted with ethyl acetate. The combined extracts were washed with saturated sodium bicarbonate and then concentrated to afford 2.86 g (83.9%) of 3-ethyl-6-fluoro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine as a white solid. LC/MS (EI) tR 3.5 (Method E), m/z 250 (M++1).

The synthetic route of 693287-79-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Dunn, Robert F.; Kuester, Eric Mikal; Conticello, Richard D.; Hopper, Allen T.; US2007/254913; (2007); 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

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

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

To a solution of 1-bromo-4-(ethylsulfonyl)benzene (1.50 g) in 1,4-dioxane (20 mL) were added diethyl malonate (1.16 g), potassium phosphate (3.84 g), biphenyl-2-yl(di-tert-butyl)phosphine (108 mg) and palladium acetate (II) (40 mg). The reaction solution was purged with argon, and the mixture was heated under reflux for 12 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane = 10:90 – 50:50, volume ratio) to give a colorless oil. A solution of the obtained oil in N,N-dimethylformamide (20 mL) was purged with nitrogen, sodium hydride (60%, oil, 213 mg) was added under ice-cooling, and the mixture was stirred at 0C for 15 min. To the reaction solution was added a solution of 4-(iodomethyl)tetrahydro-2H-pyran (1.15 g) in N,N-dimethylformamide (10 mL) at 0C, and the mixture was stirred for 3 hr at 90C. The reaction mixture was concentrated under reduced pressure, saturated aqueous ammonium chloride solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane = 10:90 – 40:60, volume ratio) to give a colorless oil. To a solution of the obtained oil in a mixed solvent of tetrahydrofuran (40 mL) and methanol (20 mL) was added 2M aqueous sodium hydroxide solution (10 mL), and the mixture was stirred at 60C for 3 hr. The reaction solution was cooled to room temperature, and acidified with 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give the title compound (1.33 g, yield 67%) as colorless crystals. MS:327(MH+). Reference Example 67 4-[4-(ethylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one, 101691-94-5

As the paragraph descriping shows that 101691-94-5 is playing an increasingly important role.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP2149550; (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

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

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.

To a mixture of 4-iodo-lH-pyrazole (2.0 g, 10.3 mmol) and Cs2CO3 (5.04 g, 15.5 mmol) in MeCN (28 mL) was added 2-(3- bromopropoxy)tetrahydro-2H-pyran (1.84 mL, 10.8 mmol) and the mixture stirred at T overnight. The crude reaction mixture was poured into water and extracted with EtOAc (x 3). The combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by FCC, using a gradient of 0-80% EtOAc in cyclohexane, to give the title compound (2.95 g, 81%). NMR (300 MHz, CDC13): 150- 1.58 (4H, m), 1.65-1.90 (2H, m), 2.12 (2H, qn, J = 6.4 Hz), 3.35 (1H, dt, J = 10.2, 5.9 Hz), 3.46-3.54 (1H, m), 3.73 (1H, dt, J = 10.2, 5.9 Hz), 3.80-3.88 (1H, m), 4.26 (2H, td, J = 6.9, 1.5 Hz), 4.54 (1H, dd, J = 4.5, 3.1 Hz), 7.46 (1H, s), 7.50 (1H, s)., 33821-94-2

As the paragraph descriping shows that 33821-94-2 is playing an increasingly important role.

Reference£º
Patent; CHIESI FARMACEUTICI S.P.A.; ALCARAZ, Lilian; PANCHAL, Terry Aaron; JENNINGS, Andrew Stephen Robert; CRIDLAND, Andrew Peter; HURLEY, Christopher; WO2014/194956; (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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A solution of N,N-diisopropylamine (3.65 mL) in tetrahydrofuran (50 mL) was purged with nitrogen, a 1.6M n-butyllithium hexane solution (16.1 mL) was added at -78C, and the mixture was stirred at -78C for 30 min. To the reaction solution was added dropwise a solution of ethyl [6-(methylsulfanyl)pyridin-3-yl]acetate (4.55 g) in tetrahydrofuran (40 mL), and the mixture was stirred at -78C for 30 min. To the reaction solution was added a solution of 4-(iodomethyl)tetrahydro-2H-pyran (5.83 mL) in tetrahydrofuran (40 mL), and the mixture was stirred at -78C for 2 hr. The reaction solution was warmed to room temperature, and stirred at room temperature for 3 days. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane = 10:90 – 50:50, volume ratio) to give the title compound (3.90 g, yield 59%) as a pale-yellow oil. MS:310(MH+). _, 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; Takeda Pharmaceutical Company Limited; EP2149550; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics