Analyzing the synthesis route of 1768-64-5

1768-64-5, As the paragraph descriping shows that 1768-64-5 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.

4- (Pheyiylmethyl) morpholin-2-ylj (tetrahydro-2H-pyran-4-yl) methanone (8b); An inerted 6L reactor is charged with THF (242.5 mL), magnesium (54.47 g, 2240mmol) and 5% of the total amount of 4-chlorotetrahydropyran (12.28 mL, 112 mmol). Then, a small amount of methyl iodide (0.5 mL) and one iodine crystal is added. The reaction mixture is stirred and heated up to 64-66C. After initiation, the remaining 4- chlorotetrahydropyran (233.22 mL, 2127 mmol) diluted in THF (890 mL) is slowly added over 135 mins. The mixture is heated up for 30 additional minutes before being cooled to 0C. Then, the Weinreb amide 2b (370 g, 1400 mmol) diluted in THF (2777 mL) is added over 180 mins between 0-4C and the mixture is stirred for a further 60 mins. Then, acetic acid (48 mL, 0.83 mmol) is added to the mixture followed by a 55/45 : v/v : saturated NH4Cl/Ha0 mixture (2590 mL) keeping the temperature below 9C. The organic layer is washed with a 60/40: v/v: saturated NH4CI/H20 mixture (500 mL) and, after separation, toluene (1800 mL) and water (1800 mL) is added to the organic solution. Then after extraction, water (1100 mL) is added to the toluene mixture which is basified with 3.68 M Na2CO3aq (148 mL). The organic layer is dried over MgS04, filtered and concentrated under reduced pressure to dryness to yield compound 8b as the free base (400. 8 g, 98. 6% yield).

1768-64-5, As the paragraph descriping shows that 1768-64-5 is playing an increasingly important role.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2005/47272; (2005); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 14774-36-8

14774-36-8, The synthetic route of 14774-36-8 has been constantly updated, and we look forward to future research findings.

14774-36-8, (Tetrahydropyran-3-yl)methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 85: Tetrahydro-2H-pyran-3-ylmethyl methanesulfonateTo tetrahydro-2H-pyran-3-ylmethanol (4.92g) in dry dichloromethane (140 ml) at O0C and under nitrogen, was added anhydrous triethylamine (13.6 ml) in one go, followed by mesyl chloride (4.3 ml) dropwise over 5 minutes. The reaction was allowed to warm to room temperature and stirred at this temperature overnight. The reaction was quenched with saturated aqueous sodium bicarbonate (50 ml). The organic layer was separated, passed through a hydrophobic frit to dry and concentrated in vacuo to yield a red oil (8.8 g).1H NMR (CDCI3): delta 4.18-4.08 (2H, m), 3.94-3.88 (1 H, m), 3.81 (1 H, m), 3.51-3.43 (1 H, m), 3.37-3.31 (1 H, m), 3.01 (3H, s), 2.07 (1 H, m), 1.85 (1 H, m), 1.72-1.56 (2H, m), 1.47-1.36 (1 H, m).

14774-36-8, The synthetic route of 14774-36-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/101867; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 85064-61-5

As the paragraph descriping shows that 85064-61-5 is playing an increasingly important role.

85064-61-5,85064-61-5, Tetrahydropyranyl-4-acetic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 4 1 -(4-(4-(2-((2,6-difluorobenzyl)oxy)- 1,1,1 ,3 ,3 ,3-hexafluoropropan-2-yl)phenyl)-4-((4- fluorophenyl)sulfonyl)piperidin-l-yl)-2-(tetrahydro-2H-pyran-4-yl)ethanone Hunig’s base (8.57 mu, 0.049 mmol) was added to a mixture of 4-(4-(2-((2,6- difluorobenzyl)oxy)- 1,1,1 ,3 ,3 ,3 -hexafluoropropan-2-yl)phenyl)-4-((4- fluorophenyl)sulfonyl)piperidine (10 mg, 0.016 mmol), 2-(tetrahydro-2H-pyran-4- yl)acetic acid (2.83 mg, 0.020 mmol) and (benzotriazol-1- yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (8.68 mg, 0.020 mmol) in acetonitrile (0.5 mL) at room temperature. After 1 h at room temperature, LCMS analysis showed that the reaction was complete. The crude material was purified via preparative LC/MS with the following conditions: Column: Waters XBridge C18, 19 x 250 mm, 5- muiotaeta particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: 30- 100percent B over 20 minutes, then a 5-minute hold at 100percent B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give Example 4 (7.7 mg, 62percent yield). LC/MS (M+l): 738.2; LC retention time: 2.30 min (analytical HPLC Method B); IH NMR (500MHz, 1 : 1 mixture of CDCI3-CD3OD) delta ppm 7.64 (d, J=8.3 Hz, 2H), 7.47 – 7.39 (m, 3H), 7.30 – 7.22 (m, 2H), 7.06 – 6.96 (m, 4H), 4.71 (s, 2H), 4.25 (s, IH), 4.05 (d, J=13.9 Hz, IH), 3.96 – 3.85 (m, 2H), 3.46 – 3.37 (m, 2H), 3.04 (t, J=12.1 Hz, IH), 2.73 (d, J=12.2 Hz, IH), 2.67 – 2.55 (m, 2H), 2.52 – 2.24 (m, 4H), 2.06 – 1.93 (m, IH), 1.72 – 1.59 (m, 2H), 1.39 – 1.24 (m, 2H).

As the paragraph descriping shows that 85064-61-5 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; DUAN, Jingwu; DHAR, T.G. Murali; JIANG, Bin; KARMAKAR, Ananta; GUPTA, Arun Kumar; LU, Zhonghui; WO2015/103510; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 14774-37-9

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

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.

Step 1 [0339] (Tetrahydro-2H-pyran-4-yl)methanol (1.00g, 8.61 mmol) was dissolved in THF (3.0 mL), a solution of sodium hydroxide (0.689 g, 17.2 mmol) dissolved in water (0.69 mL) and a solution of p-toluenesulfonyl chloride (3.28 g, 17.2 mmol) dissolved in THF (3.0 mL) were added thereto, and the mixture was stirred at room temperature overnight. Then, 12 mol/L hydrochloric acid (2.0 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (heptane/ethyl acetate = 80/20 to 50/50), whereby (tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate (1.22 g, yield 52%) was obtained. 1H NMR (300 MHz, CDCl3, delta): 7.82-7.76 (m, 2H), 7.37-7.33 (m, 2H), 3.98-3.90 (m, 2H), 3.86 (d, J = 6.6 Hz, 2H), 3.34 (td, J = 11.7, 2.2 Hz, 2H), 2.46 (s, 3H), 2.01-1.87 (m, 1H), 1.61-1.56 (m, 2H), 1.30-1.24 (m, 2H)

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

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

Analyzing the synthesis route of 1245724-46-2

As the paragraph descriping shows that 1245724-46-2 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1245724-46-2,(S)-Tetrahydro-2H-pyran-3-amine hydrochloride,as a common compound, the synthetic route is as follows.

DIPEA (6.99 mL, 40.00 mmol) was added to ethyl 6-bromo-4-chloroquinoline-3- carboxylate (3.15 g, 10 mmol) and (5)-tetrahydro-2H-pyran-3-amine hydrochloride (1.376 g, 10.00 mmol) in DMA (30 mL) at 25C under air. The resulting solution was stirred at 80C for 16 h. The reaction mixture was diluted with water (100 mL), the precipitate was collected by filtration, washed with water (20 mL) and dissolved into 250 mL EtOAc/DCM (1 : 1). The formed mixture was dried over MgSCM, filtered and evaporated to afford crude (5)-ethyl 6-bromo-4-((tetrahydro-2H-pyran- 3 -yl)amino)quinoline-3 -carboxylate (3.16 g, 83%) as a white solid. The product was used in the next step directly without further purification. NMR Spectrum; 1H NMR (300MHz, DMSO-d6) delta 1.36 (3H, t), 1.70-1.74 (1H, m), 1.75-1.77 (2H, m), 2.03-2.05 (1H, m), 3.58-3.61 (3H, m), 3.80-3.85 (1H, m), 4.01-4.03 (1H, m), 4.35 (2H, q), 7.80 (1H, d), 7.89 (1H, dd), 8.58 (1H, s), 8.67 (1H, d), 8.93 (1H, s). Mass spectrum: m/z: ES+ [M+H]+ 379, 381., 1245724-46-2

As the paragraph descriping shows that 1245724-46-2 is playing an increasingly important role.

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

Downstream synthetic route of 61363-56-2

As the paragraph descriping shows that 61363-56-2 is playing an increasingly important role.

61363-56-2, 2H-Pyran-3,5(4H,6H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

61363-56-2, EXAMPLE 1 5-(3-bromo-4-fluorophenyl)-5,10-dihydro-1H,3H-dipyrano[3,4-b:4,3-e]pyridine-4,6(7H,9H)-dione A solution of tetrahydropyran-3,5-dione (Terasawa, J. Org. Chem. (1977), 42, 1163-1169) (1.2 g, 10.5 mmol), 3-bromo-4-fluorobenzaldehyde (1.1 g, 5.4 mmol) and 2.0M ammonia in ethyl alcohol (8 mL, 16 mmol) was heated in a sealed tube to 80 C. for 36 hours and then allowed to cool to ambient temperature. The insolubles were filtered off and the filtrate evaporated to dryness. The residue was purified by flash chromatography over silica gel (5% methanol/methylene chloride) to provide an orange foam that was triturated with ether and ethyl acetate to provide the title compound (111 mg) as an orange solid. mp>250 C.; MS (APCI(+)) m/z 392 (M-H)-; 1H NMR (DMSO-d6) delta 4.06 (s,4H), 4.41-4.60 (AB qu, 4H), 4.94 (s, 1H), 7.19-7.32 (m, 2H), 7.42 (dd, 1H), 10.12 (br s, 1H); Anal. Calcd for C17H13BrFNO4.0.5 H2O: C, 50.64; H, 3.49; N, 3.47. Found: C, 50.66; H, 3.56; N, 3.90.

As the paragraph descriping shows that 61363-56-2 is playing an increasingly important role.

Reference£º
Patent; Abbott Laboratories; US6642222; (2003); B2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Some tips on 4677-20-7

4677-20-7, 4677-20-7 4-(2-Bromoethyl)tetrahydropyran 22637012, aTetrahydropyrans compound, is more and more widely used in various fields.

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.

A stirred mixture b-ketoester 7 (550 mg, 1.65 mmol), bromide 8 (335 mg, 1.73 mmol), KI (302 mg, 1.8 mmol), K2CO3 (251 mg, 1.8 mmol) and dry DMF (5 mL) was heated at 70 C for 3 h. The mixture was diluted with EtOAc (90 mL), washed with 1% aq HC1 (15 mL) and brine (15 mL), and dried over Na2S04. Removal of the solvent left a yellow oil (1.34 g) which was chromatographed on a 12 g silica cartridge, eluted with a 0 – 70% EtOAc in hexanes gradient, to give P3-001 (495 mg, 67% yield). LC-MS tR 5.41 min, m/z 446.

4677-20-7, 4677-20-7 4-(2-Bromoethyl)tetrahydropyran 22637012, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; FOX CHASE CHEMICAL DEVELOPMENT CENTER, INC.; SMITHGALL, Thomas; REITZ, Allen; WROBEL, Jay; TICE, Colin; HAIMOWITZ, Thomas; CARLSEN, Marianne; LOUGHRAN, Marie; YE, Hong; (183 pag.)WO2020/81856; (2020); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Analyzing the synthesis route of 1228779-96-1

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

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.

General procedure: To a solution of appropriate crude acid (1 eq) in CH2Cl2 wereadded EDCI (3 eq), DMAP (0.3 eq) and DIPEA (3 eq). The solutionwas stirred at room temperature for 0.5 h and compound 23 [7] (0.8eq) was added. The resulting mixture was stirred for another 8 hand water was added. The layers were separated, and the aqueouslayer was extracted with CH2Cl2. The combined organic layer waswashed with brine, dried over anhydrous Na2SO4, filtered, andconcentrated under vacuo. The residue was prified by chromatography(CH2Cl2/CH3OH 40:1) to provide target compounds 27a-i,28a-d and 34a-c.

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

Reference£º
Article; Liu, Xiaohua; Zhang, Yu; Huang, Wenjing; Luo, Jia; Li, Yang; Tan, Wenfu; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 149 – 165;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 125995-03-1

125995-03-1, The synthetic route of 125995-03-1 has been constantly updated, and we look forward to future research findings.

125995-03-1, Atorvastatin lactone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 17: (2R,4R)-1-[2-(4,6-Dihydroxytetrahydro-2-pyranyl)-ethyl]-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid phenylamide (18) (synthesis from Atorvastatin).; [Show Image] The atorvastatin lactone (21.6 g, 0.04 mol) was dissolved in anhydrous methylene chloride (500 ml) and then cooled to – 78 C with help of dry ice. DIBAL (80 ml, 1M solution in toluene) was added dropwise at the same temperature and stirring continued for 1 hour. The mixture was then quenched with 10 % solution of Rochelle’s salt (100 ml) and allowed to warm to room temperature. After addition of further methylene chloride (300 ml) and water (200 ml) concentrated HCl (50 ml) was added. Organic phase was separated and water phase was extracted with methylene chloride (2 x 200 ml). The combined organic phases were washed with 1 M HCl solution (2 ¡Á 100 ml), saturated NaHCO3 solution (2 ¡Á 100 ml) and brine (100 ml) and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure to yield 20.6 g (95 %) of pure lactol 18. LC-MS (ESI+) m/z 543 (M+1), 507,414,388.

125995-03-1, The synthetic route of 125995-03-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Ratiopharm GmbH; EP1834944; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 2081-44-9

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

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 133 g (1.31 mol) of tetrahydropyran-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 RT and stirred for 18 h. The reaction is poured onto a stirred mixture of aq. HCl/ice. The resulting precipitate is isolated by filtration and dissolved in DCM (1 L). The organic layer is washed with 1 M aq. HCl solution (1 L), followed by sat. aq. NaHCO3 solution (1 L) and is then dried over Na2SO4. Filtration and concentration of the filtrate under reduced pressure gives 300 g of toluene-4-sulfonic acid tetrahydropyran-4-yl ester. Yield: 90%; ESI-MS: 257 [M+H]+, 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; 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