Category: Tetrahydropyrans

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.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

Into a 40-mL round-bottom flask, was placed 4-(4- [[2-(4-chlorophenyl)-4,4-dimethylcyclohex- i-en-i – ylj methyljpiperazin- 1 -yl)-2- [ i4-oxa-2,4, iO-triazatricyclo [7.5 .0.0?[3 ,7j jtetradeca- 1 (9),2,5,7- tetraen-iO-yljbenzoic acid (50 mg, 0.08 mmol, 1 equiv), DCM (3 mL), 3-nitro-4-[[(oxan-4- yl)methyljaminojbenzene-i-sulfonamide (25.2 mg, 0.08 mmol, 1.00 equiv), EDCI (30.6 mg, 0.16 mmol, 2 equiv), DMAP (39.0 mg, 0.32 mmol, 4 equiv). The resulting solution was stirred for overnight at 25 degrees C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (10:1). The crude product was purified by Flash-Prep-HPLC with the following conditions (IntelFlash-i): Column, Ci8 reversed phase column; mobile phase, Water (1OMMOL/L NH4HCO3+0.05%NH3.H20) and CH3CN (20.0% CH3CN up to 90.0% in 30 mm); Detector, UV 220 nm. This resulted in 19.1 mg (25.90%) of 4-(4- [[2-(4-chlorophenyl)-4,4-dimethylcyclohex- i-en-i -ylj methyljpiperazin- 1 -yl)N-(3-nitro-4-[[(oxan-4-yl)methylj aminojbenzenesulfonyl)-2- [ i4-oxa-2,4, 10- triazatricyclo [7.5 .0.0?[3,7j jtetradeca- 1 (9),2,5,7-tetraen- iO-yljbenzamide as a yellow solid. LCMS: (ES, m/z): M+i=923, R,T= 3.463 mm. The measurements of the retention were done with a reversed phase column (C 18). Shimadzu LCMS 2020; 50*3.0 Agilent Poroshell HPH-Ci8, 2.7um; Eluent A: water (0.05 % ammonia water); Eluent B: Acetonitrile; linear gradient from 5 % acetonitrile to 95 % acetonitrile in 7.0 minutes; Oven temperature 40 C; flow: 1.5 mL/min. ?H NMR (300 MHz, DMSO-d6,ppm) 11.91 (s, iH), 11.26 (s, iH), 8.56 (s, iH), 8.47 (d, J= 2.1 Hz, iH), 7.61 (d, J = 9.0 Hz, iH), 7.48 (d, J = 9.2 Hz, iH), 7.37 (d, J = 8.3 Hz, 2H), 7.20 (s, iH), 7.07 (d, J = 8.3 Hz, 2H), 6.99 – 6.83 (m, 2H), 6.76 (d, J = 29.2 Hz, 2H), 6.14 (s, iH), 4.21 (s, 2H), 3.85 (d, J = 9.3 Hz, 2H), 3.52 (s, 2H), 3.30 – 3.14 (m, 8H), 2.79 (s, iH), 2.23 (d, J = 20.0 Hz, 5H), 1.99 (s, 4H), 1.85 (s, iH), 1.61 (d, J= 11.3 Hz, 2H), 1.42 (s, 2H), 1.25 (s, 2H), 1.03-0.79 (m, 6H). The measurements of the NMR spectra were done with Bruker Avancelli HD300MHz with a probe head of BBOF.

1228779-96-1, 1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; LOU, Yan; (108 pag.)WO2019/40550; (2019); 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.7525-64-6,4-Methyltetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

7525-64-6, To a suspension of sodium hydride, 60% in mineral oil (207 mg, 5.17 mmol) in THF (20 mL) was added 4-methyltetrahydro-2H-pyran-4-ol (500 mg, 4.30 mmol) at 0 C. After stirring 30 min, the solution was transferred to a solution of di(pyridin-2-yl)carbonate (931 mg, 4.30 mmol) in THF (20 mL) through a cannula. The formed slurry was stirred at 0 C. for 30 min. The slurry was warmed to rt and stirred for 2 h. At room temperature, to the reaction mixture was added sat. aq. NH4Cl (1 mL) upon which brief and significant effervescence was observed. The mixture was transferred to a 250 mL separatory funnel and was diluted with Et20 (50 mL). The solution was washed with water:brine (25 mL: 25 mL). The aq. phase was extracted with EtOAc (100 mL). The combined organics were dried over MgSO4; filtered; then concentrated in vacuo. The resulting residue was dissolved in acetone and then concentrated onto Celite in vacuo. The resulting powder was subjected to SiO2 purification on the Biotage system [90 g SiO2column, hexanes:EtOAc 90:10 to 60:40 over 8 CV] to get the product as a clear oil.1H NMR (400 MHz, CHLOROFORM-d) delta 8.48-8.39 (m, 1H), 7.87-7.76 (m, 1H), 7.30-7.24 (m, 2H), 7.16-7.09 (m, 1H), 3.83-3.69 (m, 4H), 2.29-2.16 (m, 2H), 1.80 (ddd, J=14.3, 8.9, 5.9 Hz, 2H), 1.66 (s, 3H)

7525-64-6 4-Methyltetrahydro-2H-pyran-4-ol 12347118, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P.V.K. Suresh; Scola, Paul Michael; (403 pag.)US9527885; (2016); B2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4677-20-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4677-20-7,4-(2-Bromoethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

Into a 50-mL 3-necked round-bottom flask, was placed tert-butyl N-[2-[([3-[4-(3- hydroxycyclobutoxy)phenyl] -1 -(oxan-2-yl)- 1 H-pyrazol-4-yl]methyl)(methyl)amino] ethyl] – N-methylcarbamate (500 mg, 0.97 mmol, 1.00 equiv),N,N-dimethylformamide (10 mL). The temperature was cooled to 0C. To this was added sodium hydride (120 mg, 5.00 mmol, 5.15 equiv, 60% in mineral oil) in batches. The mixture was stirred for 1 h at R.T. Then to the mixture was added 4-(2-bromoethyl)oxane (470 mg, 2.43 mmol, 2.51 equiv). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 30 mL of water. The resulting solution was extracted with 3×3 0 mL of ethyl acetate. The resulting mixture was washed with 3×30 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (0%-60%). The collected fractions were combined and concentrated under vacuum. This resulted in 450 mg (74%) of tert-butyl N-methyl-N-[2- [methyl([ [1 -(oxan-2-yl)-3 -(4- [3 -[2-(oxan-4-yl)ethoxy] cyclobutoxy]phenyl)1H-pyrazol-4-yl]methyl])amino]ethyl]carbamate as yellow oil. LCMS (Method A, ESI): RT = 1.37mm, m/z =627.4 [M+H].

The synthetic route of 4677-20-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; EPIZYME, INC.; MITCHELL, Lorna, Helen; SWINGER, Kerren, Kalai; SHAPIRO, Gideon; BORIACK-SJODIN, Paula, Ann; (104 pag.)WO2016/44556; (2016); A2;,
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

2081-44-9, Tetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: Synthesis of Toluene-4-sulfonic acid tetrahydro-pyran-4-yl ester To a solution of 133 g (1.31 mol) of tetrahydro-pyran-4-ol in pyridine (1.5 L) are added 373 g (1.95 mol) of p-toluenesulfonylchloride portionwise at 10 C. After complete addition the reaction is allowed to warm to room temperature and stirred for 18 h. The reaction is poured onto a stirred mixture of aqueous HCl/ice. The resulting precipitate is isolated by filtration and dissolved in DCM (1 L). The organic layer is washed with 1M aqueous HC1 solution (1 L), followed by saturated aqueous NaHC03 solution (1 L) and is then dried over Na2S04.Filtration and concentration of the filtrate under reduced pressure gives 300 g of toluene-4- sulfonic acid tetrahydro-pyran-4-yl ester as an orange oil. Yield: 90%, ES-MS: m/z: 257[M+H], 279 [M+Na]. 1H-NMR (250 MHz, CHLOROFORM-d) delta ppm 1.66 – 1.96 (4 H, m), 2.45 (3 H, s), 3.47 (2 H, ddd, 7=11.76, 8.19, 3.50 Hz), 3.79 – 3.95 (2 H, m), 4.69 (1 H, tt, 7=8.13, 4.13 Hz), 7.35 (2 H, d, 7=8.07 Hz), 7.76 – 7.87 (2 H, m)

2081-44-9, As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BERRY, Angela; RIETHER, Doris; ERMANN, Monika; JENKINS, James Edward; MUSHI, Innocent; WO2011/88015; (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.14774-37-9,Tetrahydropyran-4-methanol,as a common compound, the synthetic route is as follows.

Prepared as described by adaptation of the following literature reference: Radziszewski, J. G. et al. J. Am. Chem. Soc. 1993, 115, 8401. To 97 g (810 mmol) of (tetrahydro-pyran-4-yl)-methanol in 2-methyltetrahydrofuran (190 mL) are added 165 mL of 50% aq. NaOH solution. To this stirred suspension is added dropwise with cooling a solution of p-toluene-sulfonylchloride (283 g, 1.46 mol) in 2-methyltetrahydrofuran (280 mL). The reaction is stirred at 30-35 C. for 18 h. The suspension is poured into a mixture of ice-water (280 mL) and aq. HCl solution (37%, 203 mL). After addition of methylcyclohexane (1.4 L) and further ice-water (0.2 L), the reaction mixture is stirred for 2 h in an ice-bath. The resulting crystalline precipitate is isolated by filtration and washed with methylcyclohexane (0.5 L) and water (0.5 L). Drying under reduced pressure at 40 C. gave 216 g of toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester. Yield: 99%; ESI-MS: 271 [M+H]+, 14774-37-9

14774-37-9 Tetrahydropyran-4-methanol 2773573, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Boehringer Ingelheim International GmbH; Riether, Doris; Binder, Florian Paul Christian; Doods, Henri; Mueller, Stephan Georg; Nicholson, Janet Rachel; Sauer, Achim; US8865744; (2014); B1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

873397-34-3, Tetrahydro-2H-pyran-3-carboxylic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: To a solution of (3-methoxy-5-methylpyrazin-2-yl)methanamine (150 mg, 979.2 mol), tetrahydro-2H-pyran-3-carboxylic acid (127.4 mg, 979.2 mol) in DCM (10 mL) was added HATU (670.2 mg, 1.8 mmol) and triethylamine (198.2 mg, 1.9 mmol). The mixture was stirred at 25¡ãC for 16 hours. The mixture was diluted with water (15 mL), extracted with DCM (3 x 30 mL). The combined organic layer was washed with brine (30 mL), dried overNa2504, filtered and concentrated. The residue was purified by preparative TLC (EAIMeO H =20/1) to give N-((3-methoxy-5-methylpyrazin-2-yl)methyl)tetrahyd ro-2H-pyran-3- carboxamide (130 mg, 50percent yield)., 873397-34-3

The synthetic route of 873397-34-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2016/174188; (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.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