Day: August 17, 2020

33821-94-2, 2-(3-Bromopropoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Potassium hydride (30% w/w in mineral oil, 2.2 g, 16.5 mmol) was suspended in 1 ,2- dimethoxyethane (20.0 mL) and the suspension cooled to 0-5C (ice bath). A solution of 2- methyl-2-(methylsulfonimidoyl)propanenitrile (Int-5, 2.0 g, 13.7 mmol) in 1 ,2-dimethoxyethane (15 mL) was added dropwise over 10 min. The ice bath was removed and the mixture was stirred for 3 h at room temperature. After that, it was cooled again to 0-5C and tetrabutylammonium bromide (235 mg, 730 muiotaetaomicron) followed by 2-(3-bromopropoxy)tetrahydro-2H-pyran (Int-6, 3.95 g, 3.00 mL, 17.7 mmol) was added. The reaction mixture was stirred for 16 h at room temperature. Then, the mixture was poured onto a saturated aqueous solution of sodium hydrogencarbonate (60 mL) and diluted with ethyl acetate (180 mL). After phase separation, the aqueous phase was extraced with ethyl acetate (2 x 50 mL), the combined organic extracts were dried (sodium sulfate) and concentrated in vacuo to afford a yellow biphasic oil as crude product. This was purified by column chromatography (silica gel, 100 g, eluting with ethyl acetate / n- heptane, gradient 40:60 to 100:0) to yield, after drying in vacuo (50C, 5 mbar), the title compound as mixture of diastereoisomers as a colorless viscous oil (3.28 g, 83%). HPLC (method LCMS_gradient) tR = 1.6 min. 1H NMR (CDC13, 400 MHz): delta 1.47-1.60 (m, 4 H), 1.68- 1.77 (m, 1 H), 1.76 (br s, 6 H), 1.78-1.88 (m, 3 H), 3.06 & 3.07 (2s, 3 H, dias ), 3.20-3.41 (m, 2 H), 3.45-3.54 (m, 2 H), 3.79-3.91 (m, 2 H), 4.56-4.60 (m, 1 H). MS (ES+) m/z 205.1 [M+H- (CsHgO)] .

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

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

220641-87-2, N-Methyltetrahydro-2H-pyran-4-amine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 10; 1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-{4-[methyl-(tetrahydro-pyran-4-yl)-amino]-butyl}-[1,4]diazepan-5-one; 1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-{4-[methyl-(tetrahydro-pyran-4-yl)-amino]-butyl}-[1,4]diazepan-5-one; A solution of 0.100 g (0.20 mmol) of 1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-4-(4-iodo-butyl)-[1,4]diazepan-5-one (example 9B) in 3.1 ml of DMA was treated with free methyl-(tetrahydro-pyran-4-yl)-amine in 1 ml of toluene [0.035 g (0.22 mmol) methyl-(tetrahydro-pyran-4-yl)-amine hydrochloride were dissolved in 0.8 ml of 0.5 N NaOH was extracted with toluene (2 ml). The organic phase was dried over Na2SO4] and stirred for 22 h at RT, 0.06 ml (0.40 mmol) of Et3N was added and stirring was continued for 18 h at 50 C. Again methyl-(tetrahydro-pyran-4-yl)-amine in 1 ml of CH2Cl2 [0.035 g (0.22 mmol) methyl-(tetrahydro-pyran-4-yl)-amine hydrochloridewere dissolved in 0.5 ml aqueous 10% NaCl solution/0.4 ml of 1 N NaOH was extracted with CH2Cl2 (1 ml). The organic phase was dried over Na2SO4] was added and heated for 9 h at 50 C. The reaction was extracted with aqueous saturated NaHCO3/Et2O (3¡Á). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4), concentrated and evaporated. Purification by catridges, Si-Amine, 70 ml, 20 g (n-heptane/EtOAc 1:4 to 1:9) gave 0.004 g (4%) of the title compound as a light yellow semisolid. MS: 482.3 (MH+, 2Cl).

The synthetic route of 220641-87-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Aebi, Johannes; Green, Luke; Mattei, Patrizio; Ricklin, Fabienne; Roche, Olivier; Zahm, Peter; US2007/249589; (2007); 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

2-[4-(2,3-Difluorophenoxy)butoxy]-tetrahydropyran (20) To a solution of 2-(4-bromobutoxy)-tetrahydropyran (18) (1 equi.) and commercially available 2,3-difluorophenol (19) (1 equi.) in DMF (3 mL/mmole), cesium carbonate (1.25 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane (1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) and recrystallization from acetonitrile gave 2-[4-(2,3-difluorophenoxy)-butoxy]-tetrahydropyran(20), as a white solid (84%).

31608-22-7 2-(4-Bromobutoxy)tetrahydro-2H-pyran 559019, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Wand, Michael; Gough, Neil; Chen, Xin Hua; US2003/17278; (2003); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125552-89-8, 4-(Bromomethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To the stirred solution of lH-indole-2-carbaldehyde (1, 1.0 g, 6.89 mmol) in N, N-dimethylformamide (10 mL), cesium carbonate (6.70 g, 20.68 mmol) and 4- (bromomethyl)tetrahydro-2H-pyran (1.48 g, 8.27 mmol) were added at room temperature. The reaction mixture was stirred at room temperature for 1 h. After completion of reaction, reaction mixture was diluted with water and extracted with ethyl acetate (200 mL x 2). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude was purified by CombiFlash using 12 g RediSep and 5% ethyl acetate in hexane as eluent to afford l-((tetrahydro-2H-pyran-4-yl)methyl)-lH-indole-2-carbaldehyde as white solid). Yield: 0.80 g (48%). MS (ESI);243.13 m/z found: 244.17[M+H]+1.

125552-89-8 4-(Bromomethyl)tetrahydropyran 2773286, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; JUBILANT BIOSYS LIMITED; HALLUR, Gurulingappa; DURAISWAMY, Athisayamani Jeyaraj; PURRA, Buchi Reddy; RAO, N.V.S.K.; RAJAGOPAL, Sridharan; (247 pag.)WO2019/58393; (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.4295-99-2,4-Cyanotetrahydro-4H-pyran,as a common compound, the synthetic route is as follows.

To a solution of tetrahydro-2H-pyran-4-carbonitrile (2.15 g, 19.34 mmol) in dry THE (15 mL) cooled at -78 C, LiHDMS solution (1M in THE, 24.2 mL, 24.2 mmol) was added dropwise under nitrogen atmosphere and the mixture was stirred at this temperature for lh. Then, a solution of (3-iodopropoxy)methylbenzene (6.14 g, 22.2 mmol) in dry THE (10 mL) was added and the reaction mixture was allowed to reachrt and stirred overnight. The solvent was evaporated and the residue was diluted with water and Et20. The phases were separated and the aqueous phase was extracted several times with Et20. The organic phases were combined and washed with water and brine, the solvent was evaporated and the residue thus obtained was purified by flash chromatography on silica gel, gradient CH to CH:AcOEt (80:20) to give the titlecompound (4.35 g, 87% yield).HPLC-MS (Method B): Ret, 2.28 mm; ESI+-MS mlz, 260.31 (M+H).

As the paragraph descriping shows that 4295-99-2 is playing an increasingly important role.

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; GARCIA-LOPEZ, Monica; ALMANSA-ROSALES, Carmen; (168 pag.)WO2018/108319; (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.40191-32-0,Tetrahydro-2H-pyran-4-carbonyl chloride,as a common compound, the synthetic route is as follows.

The compound, Methyl (2S)-2-amino-3-{N-[4-(4-trifluoromethylphenoxy)phenyl]-N-methanesulfonylamino}propionate, was prepared from 4-(4-trifluoromethylphenoxy)aniline in accordance with the sequence of general procedure I, II, III, and IV (GP-I, GP-II, GP-III, and GP-IV) as described herein above for reference examples. To a solution of Methyl (2S)-2-amino-3-{N-[4-(4-trifluoromethylphenoxy)phenyl]-N-methanesulfonylamino}propionate (86 mg, 0.2 mmol) in CH2Cl2/THF (1.5 mL/1.5 mL) was added 2,6-lutidine (0.1 mL, 1.2 mmol) and then 4-tetropyranecarboxyl chloride (119 mg, 0.8 mmol) at 0 C. The mixture was allowed to warm to rt and stirred for 1 h. The mixture was poured into Et2O/H2O (100 mL/100 mL) and HCl(aq) (2 N, 5 mL) was added. The organic was washed with NaOH(aq) (10%, 10 mL), H2O (40 mL), brine (50 mL), dried (Na2SO4), and filtered. After removal of solvent, the product was dried in vacuo to give 102 mg of Methyl (2S)-2-[(tetrahydropyran-4-yl)carbonylamino]-3-{N-[4-(4-trifluoromethylphenoxy)phenyl]-N-methanesulfonylamino}propionate (94%) as a white solid. 1H NMR (300 MHz, CDCl3) delta 7.62 (d, J=9.0 Hz, 2H), 7.33 (d, J=9.0 Hz, 2H), 7.12-7.05 (m, 4H), 6.45 (d, J=9.0 Hz, 1H), 4.68-4.62 (m, 1H), 4.17-3.98 (m, 4H), 3.59 (s, 3H), 3.47-3.38 (m, 2H), 2.90 (s, 3H), 2.42-2.35 (m, 1H), 1.80-1.76 (m, 4H); MS (EI, m/z): 545 (M++1, 100).

The synthetic route of 40191-32-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; YANG, Shyh-Ming; Wang, Bingbing; Scannevin, Robert; Rhodes, Kenneth; Lagu, Bharat; Wilson, Lawrence J.; Karnachi, Prabha; Murray, William V.; US2008/85893; (2008); A1;,
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

General procedure: A mixture of bromo-ketone (0.6 g,2.9 mmol), amide (0.55 g, 3.6 mmol, 1.25 equiv), and silver triflate (0.9 g,3.6 mmol, 1.25 equiv) in ethyl acetate (4 mL) was heated to 50?70 ¡ãC. After thereaction was deemed complete by HPLC analysis, the mixture was cooled to 20 ¡ãC and diluted with ethyl acetate (3 mL). A solution of sat?d NaCl (3?4 mL)was added and the mixture stirred at 20 ¡ãC for at least 4 h. The silver salts (AgBr and AgCl) are removed by filtration and the resulting biphasic solution transferred to a separatory funnel and the layers separated. The organic layer isthen washed with water (4 mL), 5percent NaHCO3 (4 mL), 1 N HCl (4 mL), and water(4 mL). The organic layer is concentrated to dryness and the residue purified by flash column chromatography (5percent EtOAc/hexanes) to obtain pure oxazole product.

344329-76-6 Tetrahydro-2H-pyran-4-carboxamide 13197203, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Article; Bailey, Jessica L.; Sudini, Ravinder R.; Tetrahedron Letters; vol. 55; 27; (2014); p. 3674 – 3677;,
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.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

To a solution of tetrahydro-2H-pyran-4-ol (10.0 g) in DCM (200 mL)was added TEA (12.9 g) and methanesulfonyl chloride (11.3 g). The mixture was stirred at 0C for 1 hour, and then washed with H20. The organic layer was dried over Na2SO4 and concentrated to afford10 tetrahydro-2H-pyran-4-yl methanesulfonate (15.5 g).

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

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CHEN, Weichun; IGBOKO, Ebere F; LIN, Xichen; LU, Hongfu; REN, Feng; WREN, Paul Bryan; XU, Zhongmiao; YANG, Ting; ZHU, Lingdong; WO2015/181186; (2015); 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.36838-71-8,4-Methylenetetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A mixture of 4-methylene-tetrahydropyran (50 mg) and 9-bora-bicyclo{3.3.1}nonane (0.5 M solution in tetrahydrofuran, 1 mL) is stirred for 6 h at room temperature. The solution is used directly for the next step.

The synthetic route of 36838-71-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; LANGKOPF, Elke; WAGNER, Holger; WO2014/86712; (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.103260-44-2,Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate,as a common compound, the synthetic route is as follows.

Lithium aluminum hydride (2M solution in THF, 40.66 ml, 81.3 mmol) was cooled at 0 C and a solution of ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (14.0 g, 81.3 mmol) in THF (70 ml) was added dropwise. Ethyl acetate (20 ml) was added to the reaction mixture dropwise at 0 C and the resulting mixture was allowed to stir for 16 h. The reaction mixture was filtered through Celite and the filtrate was concentrated to give crude compound. The crude material was purified by column chromatography using mobile phase 0-65% ethyl acetate in hexane to afford the title compound (66.1%). ?H NMR (400MHz, CDC13) & 5.71 (s, 1H), 4.18-4.15 (m, 2H), 3.81-3.75 (m, 4H), 3.05-3.02 (m, 2H), 2.37-2.34 (m, 2H), 1.32- 1.31 (m, 3H).

The synthetic route of 103260-44-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; EPIZYME, INC.; CHESWORTH, Richard; MITCHELL, Lorna, Helen; CAMPBELL, John, Emmerson; REITER, Lawrence, Alan; SWINGER, Kerren, Kalai; (387 pag.)WO2016/44626; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics