Heterocyclic Building Blocks-Tetrahydropyrans

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

4295-99-2, 4-Cyanotetrahydro-4H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step. Preparation of dideutero-(tetrahydro-2H-pyran-4-yl)methanamine: To a solution of tetrahydro-2H-pyran-4-carbonitrile (800 mg, 7.20 mmol) in THF (20 ml_) was added aluminum(lll) lithium deuteride at 0 C. The mixture was stirred at 0 C for 2 hr. To the stirred reaction mixture was sequentially added 300 uL of water, 900 muIota_ of 1 N NaOH and 300 muIota_ of water. The mixture was filtered through a thin layer of celite to remove the solid. The filtrate was dried over sodium sulfate, filtered off and concentrated in vacuo giving 700 mg of titled compound. LCMS (m/z): 1 18.2 [M+H]+, retention time = 0.25 min. The crude product was used directly for next step.

4295-99-2 4-Cyanotetrahydro-4H-pyran 11815837, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; NOVARTIS AG; ANTONIOS-MCCREA, William R.; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; MARTIN, Eric J.; PAN, Yue; LIN, Xiaodong; PFISTER, Keith B.; RENHOWE, Paul A.; SENDZIK, Martin; SUTTON, James; WAN, Lifeng; WO2012/101062; (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.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

Step 7: Preparation for tetrahydro-2H-pyran-4-ol (0177) To a solution of lithium aluminium hydride (0.95 g, 25 mmol) in tetrahydrofuran (40 mL) was dihydro-2H-pyran-4(3H)-one (2.0 g, 20 mmol) with stirring at 0 C. The mixture was stirred at ambient temperature for 2 hours, quenched with sodium hydroxide (30%, 0.45 g), filtered, dried over magnesium sulfate, filtered and concentrated to obtain a crude product as a light-yellow oil (2.0 g, yield=95%).

The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BEIJING SCITECH-MQ PHARMACEUTICALS LIMITED; SHENG, Wang; YANG, Leifu; PAN, Zhiyong; (46 pag.)US2017/355683; (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.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 8- mL round-bottom flask, was placed 4-(4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-l-en-l- yl]methyl]piperazin-l-yl)-2-[l4-thia-2,4,l0-triazatricyclo[7.5.0.0A[3,7]]tetradeca-l(9),2,5,7- tetraen-lO-yl]benzoic acid (30 mg, 0.05 mmol, 1 equiv), 3-nitro-4-[[(oxan-4- yl)methyl]amino]benzene-l-sulfonamide (17 mg, 0.06 mmol, 1.20 equiv), EDCI (18 mg, 0.09 mmol, 2 equiv), DMAP (23 mg, 0.19 mmol, 4 equiv), DCM (3 mL). The resulting solution was stirred for overnight at room temperature. The resulting mixture was concentrated. The crude product was purified by Flash-Prep-HPLC with the following conditions (IntelFlash-l): Column, C18 silica gel; mobile phase, Water(0. l%FA) and ACN (48.0% ACN up to 53.0% in 7 min, hold 95.0% in 1 min, down to 48.0% in 1 min within 5 ; Detector, UV 254 nm. This resulted in 10.6 mg (24.15%) of 4-(4-[[2-(4-chlorophenyl)-4,4- dimethylcyclohex- l-en- l-yl]methyl]piperazin- l-yl)-N-(3-nitro-4-[[(oxan-4- yl)methyl]amino]benzenesulfonyl)-2-[l4-thia-2,4,l0-triazatricyclo[7.5.0.0A[3,7]]tetradeca- l(9),2,5,7-tetraen-l0-yl]benzamide as a yellow solid. LC-MS: (ES, m/z ): M+l=939, R,T= 3.55 min. The measurements of the retention were done with a reversed phase column (C18). Shimadzu LCMS 2020; 50*3.0 Kinetex 2.6u XB-C18 , 2.6 microm; Eluent A: water (0.05 % TFA); Eluent B: Acetonitrile; linear gradient. H-NMR: (CDC13, 300 ppm): 8.7l(s, 1H), 8.49 (s, 1H), 7.99-7.97(m, 1H), 7.8l-7.77(m, 1H), 7.38-7.28(m, 4H), 7.0l-6.93(m, 2H), 6.88- 6.72(m, 3H), 3.36(s, 1H), 4.06-3.26(m, 18H), 2.73-2.22(m, 6H), 2. l3-l.73(m, 3H), 1.79- l.25(m, 6H), l.00(s, 6H).

As the paragraph descriping shows that 1228779-96-1 is playing an increasingly important role.

Reference£º
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (475 pag.)WO2020/41406; (2020); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics