Month: September 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

To an ice-cooled solution of oxan-4-ol (1.00 g, 9.79 mmol), Et3N (1.36 ml, 9.79 mmol) and catalytic amount DMAP in 20 ml of CH2Cl2 was added dropwise MsCl (0.76 ml, 9.79 mmol). The resulting mixture was stirred for 1 h and diluted with water. The mixture was extracted with CH2Cl2. The organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was pure enough for use in the next step (1.65 g, 93.5 % yield).

2081-44-9, 2081-44-9 Tetrahydro-2H-pyran-4-ol 74956, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Zhang, Dengyou; Ai, Jing; Liang, Zhongjie; Li, Chunpu; Peng, Xia; Ji, Yinchun; Jiang, Hualiang; Geng, Meiyu; Luo, Cheng; Liu, Hong; Bioorganic and Medicinal Chemistry; vol. 20; 17; (2012); p. 5169 – 5180;,
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.1197-66-6,2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one,as a common compound, the synthetic route is as follows.

A 2 L RBF under light nitrogen flow was charged with 2,2,6,6-tetramethyldihydro-2H-pyran-4(3H)-one (1.00 equiv; 49.10 mL; 43.45 g), (a known compound which may be prepared as described in, for example, MAGNUS, P., et al., ?Synthesis of the ABCD-rings of the insecticidal indole alkaloid nodulisporic acid?, Tet. Lett., 1999, pp 6909-6912, Vol. 40) 2-methyl-THF (375.00 mL; 322.05 g) and DBU (76.67 mL; 77.67 g). The resulting mixture was stirred and cooled to about 2 C. with a water-ice bath. NfsulphF (1.20 equiv; 56.07 mL; 94.20 g) was introduced into a dropping funnel and the NfsulphF was then added to the reaction mixture over 20 minutes, with a light exotherm is observed. After complete addition, the water-ice bath was taken away and the temperature allowed to rise to room temperature. Precipitation was observed to start forming, resulting in a yellow suspension. The yellow suspension was stirred overnight at room temperature and yielded yield a brown suspension. [0249] To the brown suspension was slowly added water (1.12 L; 1.12 kg), with an observed exotherm. The resulting mixture was warmed 44 C., resulting in a multi-phase mixture with good separation (the organic layer was the top layer). The mixture was stirred for 20 minutes and the phases warm separated at about 44 C. The aqueous (orange colored) layer was returned to the RBF, and then extracted with 2-methyl-THF (185.00 mL; 158.88 g) by stirring 20 minutes at 44 C., then warm separating the resulting layers. The organic layers were then combined. Water (190.00 mL; 190.00 g) was added and the resulting mixture stir for 20 minutes, and the resulting layers warm separated at 44 C. The organic layer was then washed second time with water (190.00 mL; 190.00 g), with some white fluffy precipitation observed in the water layer. The organic layer was then evaporated on a rotavap at 45 C. The resulting biphasic residue included a thick brown bottom layer (129.17 g) and light colored material on top. To the residue was added HEPTANE 50% (a mixture of 50% n-heptane, 20% other heptane isomers and 30% methyl cyclohexane; 250.00 mL; 176.75 g), then acetonitrile (19.00 mL; 14.88 g). The resulting mixture was stirred firmly, the acetonitrile was observed to take up the oily layer, resulting in a biphasic system. The mixture was then stirred for 1 hour, the layers separated. The heptane layer was evaporated on a rotovap at 42 C. to yield the title compound as a residue (102.60 g) [0250] Actual Yield: 93.52% 102.60 g, 234.08 mmol [0251] Theoretical Yield: 100% 109.58 g, 250.00 mmol, 1197-66-6

As the paragraph descriping shows that 1197-66-6 is playing an increasingly important role.

Reference£º
Patent; Janssen Pharmaceutica NV; KOLODZIEJCZYK, Krzysztof; Stappers, Alfred Elisabeth; Teleha, Christopher A.; Weerts, Koen Johan Herman; US2014/45789; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1245724-46-2, (S)-Tetrahydro-2H-pyran-3-amine hydrochloride is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of ethyl 4-chloro-6-(6-(methoxymethyl)pyridin-3-yl)quinoline-3- carboxylate (2 g, 5.61 mmol) and (5)-tetrahydro-2H-pyran-3-amine hydrochloride (0.926 g, 6.73 mmol) in DMF (10 ml) was added DIPEA (3.5 ml, 20.04 mmol) and the solution stirred at 80C for three h then allowed to cool. The reaction mixture was stirred with water (100 ml) and the solid was filtered off, washed thoroughly with water and sucked dry. The crude product was purified by FCC, elution gradient 0 to 3% 2N methanolic ammonia in DCM and pure fractions were evaporated to dryness to afford (5)-ethyl 6-(6-(methoxymethyl)pyridin-3-yl)-4- ((tetrahydro-2H-pyran-3-yl)amino)quinoline-3-carboxylate (1.640 g, 69.4 %) as a white solid. NMR Spectrum: 1H NMR (500MHz, DMSO-d6) 5 1.36 (3H, t), 1.47 – 1.64 (1H, m), 1.67 – 1.94 (2H, m), 1.96 – 2.2 (1H, m), 3.40 (3H, s), 3.56 (1H, dd), 3.61 (2H, t), 3.87 (1H, dd), 4.22 (1H, dd), 4.36 (2H, q), 4.56 (2H, s), 7.54 (1H, dd), 7.95 (1H, d), 8.10 (1H, dd), 8.19 (1H, dd), 8.40 (1H, d), 8.91 (1H, s), 8.92 – 8.93 (1H, m), 8.94 (1H, dd). Mass Spectrum: m/z (ES+)[M+H]+ = 422., 1245724-46-2

1245724-46-2 (S)-Tetrahydro-2H-pyran-3-amine hydrochloride 60145922, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; BARLAAM, Bernard, Christophe; PIKE, Kurt, Gordon; HUNT, Thomas, Anthony; (110 pag.)WO2017/153578; (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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

General procedure: A solution of trimethyl phosphonoacetate (9.36 mmol) in THF (7 mL, 1.34 M) was added dropwise to sodium hydride (60% in mineral oil, 9.75 mmol) suspended in THF (35 mL) at 0 C. After 40 min, the pyranone (7.80 mmol), in THF (7 mL, 1.11 M), was added dropwise and the flask was heated to 25 C. After 19 h, the mixture was cooled to room temperature and quenched with saturated aqueous NH4Cl (10 mL). The precipitate was removed by filtration and the layers were separated. The aqueous layer was extracted with ether (2*20mL) and the organic fractions were combined, dried (MgSO4), filtered, and concentrated under vacuum. The crude material was purified as indicated., 1194-16-7

As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

Reference£º
Article; Shouksmith, Andrew E.; Evans, Laura E.; Tweddle, Deborah A.; Miller, Duncan C.; Willmore, Elaine; Newell, David R.; Golding, Bernard T.; Griffin, Roger J.; Australian Journal of Chemistry; vol. 68; 4; (2015); p. 660 – 679;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

720706-20-7, (4-Amino-4-tetrahydropyranyl)methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,720706-20-7

The 2-hydroxyethylamine was reacted with isobutyraldehyde according to Method B4c, Step 1 to afford 2-isopropyl-1-aza-3,8-dioxaspiro[4.5]decane

The synthetic route of 720706-20-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bayer Corporation; US6353006; (2002); B1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

344329-76-6, Tetrahydro-2H-pyran-4-carboxamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Thionyl chloride (10.0 mL, 137 mmol) was added to oxane-4-carboxamide (3.0 g, 23 mmol) and thereaction mixture was refluxed for 4 h, after which the reaction mixture was poured over ice andbasified to pH 14 with NaOH (50%). The aqueous solution was extracted with EtOAc (3 ¡Á 50 mL),dried (Na2SO4) and concentrated in vacuo to give the product as a pale yellow oil (2.4 g, 94%). Theproduct obtained did not require any further purification.IR numax 2961, 2932, 2851, 2240, 1468, 1446, 1390, 1242, 1125, 1066, 1011 cm-1;1H-NMR (CDCl3, 500 MHz): 3.91 (2H, ddd, J 11.9, 6.3, 3.6, 2¡Á2-HA), 3.61 (2H, ddd, J 11.9, 7.8, 3.3,2¡Á2-HB), 2.91-2.85 (1H, m, 4-H), 1.99-1.92 (2H, m, 2¡Á3-HA), 1.91-1.84 (2H, m, 2¡Á3-HB);13C-NMR (CDCl3, 75 MHz): 121.2, 65.6, 28.9, 25.3;HRMS (ESI+): Calculated for C6H10NO ([M+H]+): 112.0756. Found: 112.0754, Delta -1.8 ppm., 344329-76-6

The synthetic route of 344329-76-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Craven, Philip; Aimon, Anthony; Dow, Mark; Fleury-Bregeot, Nicolas; Guilleux, Rachel; Morgentin, Remy; Roche, Didier; Kalliokoski, Tuomo; Foster, Richard; Marsden, Stephen P.; Nelson, Adam; Bioorganic and Medicinal Chemistry; vol. 23; 11; (2015); p. 2629 – 2635;,
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.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

5- (4-Fluorophenyl) -4-oxo-1,4-dihydropyridazine-3-carboxylic acid ethyl ester (500.0 mg, 1.9 mmol, 1.0 eq) was dissolved in DMF (5 mL) and added Cesium carbonate (1.85 g, 5.70 mmol, 3.0 eq) and 4-bromotetrahydro-2H-pyran (628.7 mg, 3.81 mmol, 2.0 eq) were stirred at 120 C for 5 hours. The reaction was monitored by TLC, and the reaction was concentrated under reduced pressure. Ethyl acetate (15 mL) and water (20 mL) were added, and the layers were separated. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate). Esters = 8: 1 to 2: 1) to obtain the product (342.0 mg, yield: 51.9%).

25637-16-5, The synthetic route of 25637-16-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Li Lin; Wan Zhonghui; (107 pag.)CN110041316; (2019); 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

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.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

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