Category: Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

To a solution of ethyl 1 -(6-(2-(4-hydroxy-2-methylphenethyl) phenyl)pyridin-2-yl)-5- (trifluoromethyl)-1 H-pyrazole-4-carboxylate (600 mg, 1.211 mmol, preparation described in Example 1) in acetone (15 ml) was added Cs2003 (592 mg, 1.816 mmol). After stirring for 30 mi 2-(3-bromopropoxy)tetrahydro-2H-pyran (324 mg, 1.453 mmol) was added andthe reaction was heated overnight at 65C. Analysis of the reaction by TLC showed the reaction was complete. The reaction mixture was concentrated in vacuo, diluted with DCM and washed with H20. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The product was purified by chromatography on a Isco Companion. The sample was loaded on 10 g Biotage silica (Si) column then the purification was carried out using a Cyclohexane / EtOAc 100/0 to 80/20. The appropriatefractions were combined and concentrated in vacuo to give the required product as a colorless oil (710 mg, 92%). LC/MS rt = 4.62 mm m/z = 554 [M+H]-THP., 33821-94-2

As the paragraph descriping shows that 33821-94-2 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GOODMAN, Krista B.; KRAUSS, Achim Hans-Peter; LE MONNIER DE GOUVILLE, Anne-Charlotte; DODIC, Nerina; WO2015/33307; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

61363-56-2,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61363-56-2,2H-Pyran-3,5(4H,6H)-dione,as a common compound, the synthetic route is as follows.

EXAMPLE 51 4-[4-fluoro-3-(trifluoromethyl)phenyl]-1-methyl-4,9-dihydro-1H-isoxazolo[3,4-b]pyrano[4,3-e]pyridine-3,5(6H,8H)-dione The product from Example 45A (0.11 g, 1 mmol),4-fluoro-3-trifluromethylbenzaldehyde and 2H-pyran-3,5(4H,6H)-dione (0.11 g, 1 mmol) were heated in 2 mL of ethanol for 2 days. The reaction mixture was evaporated under reduced pressure and the remaining residue was triturated with methylene chloride. The resulting precipitate was filtered to provide the title compound as the filter cake. 1H NMR (300 MHz, DMSO-d6) delta 3.28 (s, 3H), 4.07 (s, 2H), 4.58 (q, 2H), 4.87 (s, 1H), 7.42 (t, 1H), 7.59 (m, 2H), 10.8 (s, 1H); MS (ESI) m/z 383 (M+H)-; Anal. Calcd for C16H12N2F4O4: C, 51.61;H, 3.22; N, 7.52. Found: C, 51.09;H, 3.11; N,,6.98.

61363-56-2 2H-Pyran-3,5(4H,6H)-dione 325287, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Drizin, Irene; Altenbach, Robert J.; Carroll, William A.; US2002/7059; (2002); 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

To a solution of N-methyltetrahydro-2H-pyran-4-amine (80 mg, 0.695 mmol) in DCM (10 mL) and pyridine (0.5 mL) was added 3-bromobenzoyl chloride (0.101 mL, 0.764 mmol) in DCM (3 mL). The mixture was stirred at room temperature for 30 mm, then 50 mL of DCM was added and the mixture was washed with water, 1 N HC1,saturated NaHCO3, brine, and concentrated to give 3-bromo-N-methyl-N-(tetrahydro-2H- pyran-4-yl)benzamide (160 mg, 77% yield). LCMS M = 298.15/300.15. Method G. Rt 2.5 54 mm., 220641-87-2

220641-87-2 N-Methyltetrahydro-2H-pyran-4-amine 6991950, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BHIDE, Rajeev S.; BATT, Douglas G.; CHERNEY, Robert J.; CORNELIUS, Lyndon A.M.; LIU, Qingjie; MARCOUX, David; NEELS, James; POSS, Michael A.; QIN, Lan-ying; RUAN, Zheming; SHI, Qing; SRIVASTAVA, Anurag S.; TINO, Joseph A.; WATTERSON, Scott Hunter; (532 pag.)WO2016/64957; (2016); A1;,
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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

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., 1245724-46-2

The synthetic route of 1245724-46-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; BARLAAM, Bernard, Christophe; PIKE, Kurt, Gordon; HUNT, Thomas, Anthony; (110 pag.)WO2017/153578; (2017); A1;,
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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.

To a solution of tetrahydro-2H-pyran-4-ylmethanol (Combi-Blocks, 2.0 g, 17.2 mmol) in 10 mL of of CH2CI2 and 10 mL of of pyridine was added p- toluenesulfonyl chloride (3.5 g, 18.1 mmol) in portions over 15 minutes. The mixture stirred at ambient temperature for 16 hours and was quenched with 10 mL of saturated, aqueous NaHCO3. The layers were separated and the aqueous layer was extracted with three 10 mL portions OfCH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) delta ppm 1.05 – 1.25 (m, 2 H), 1.40 – 1.53 (m, 2 H), 1.73 – 1.94 (m, 1 H), 2.43 (s, 3 H), 3.14 – 3.28 (m, 2 H), 3.71 – 3.84 (m, 2 H), 3.88 (d, J=6.4 Hz, 2 H), 7.48 (d, J=8.5 Hz, 2 H), 7.79 (d, J=8.5 Hz, 2 H); MS (DCI/NH3) m/z 288 (M+NH4)+, 14774-37-9

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

Reference£º
Patent; ABBOTT LABORATORIES; WO2009/67613; (2009); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

1228779-96-1, 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(0104) Compound 5K (3.39 g), Compound 5A (1.87 g), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (2.39 g), and 4-dimethylaminopyridine (1.09 g) were stirred in CH2Cl2 (40 ml) for 24 hours. The reaction was cooled and chromatographed on silica gel with 25-100% ethyl acetate/hexanes, then 10% methanol/ethyl acetate with 1% acetic acid, to give the product (1.62 g, 32%) as a white solid. 1H NMR (300 MHz, dimethylsulfoxide-d6) delta 11.65 (br s, 1H), 8.55 (br s, 1H), 8.04 (d, 1H), 7.89 (dd, 1H), 7.51 (m, 3H), 7.33 (d, 2H), 7.08 (m, 1H), 7.04 (d, 2H), 6.68 (dd, 1H), 6.39 (d, 1H), 6.19 (d, 1H), 3.84 (m, 1H), 3.30 (m, 4H), 3.07 (m, 4H), 2.73(m, 2H), 2.18 (m, 6H), 1.95 (m, 2H), 1.61 (dd, 2H), 1.38 (m, 2H), 1.24 (m, 4H), 0.92 (s, 6H).

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

Reference£º
Patent; AbbVie Inc.; Catron, Nathaniel; Lindley, David; Miller, Jonathan M.; Schmitt, Eric A.; Tong, Ping; US10213433; (2019); B2;,
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.4677-18-3,2-(Tetrahydro-2H-pyran-4-yl)ethanol,as a common compound, the synthetic route is as follows.,4677-18-3

[00107] A mixture of 2-(tetrahydro-2H-pyran-4-yl)ethanol (11.70 g, 89.9 mmol) and pyridinium chlorochromate (38.8 g, 179.8 mmol) in CH2C12 (200 mL) was stirred at 16-19 C for 17 h. TLC (petroleum ether: ethyl acetate = 3: 1) showed the reaction was complete. The mixture was filtered with Kieselguhr and the filtrate (150 mL) was used for the next step directly without further purification.

As the paragraph descriping shows that 4677-18-3 is playing an increasingly important role.

Reference£º
Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; SINGH, Suresh, B.; TICE, Colin, M.; YUAN, Jing; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; (102 pag.)WO2016/61160; (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.25850-22-0,2,2-Dimethyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

(4) (2E)-3-{3-cyano-4,6-dimethyl-1-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-[(4S)-2,2-dimethyltetrahydro-2H-pyran-4-yl]prop-2-enamide(2E)-3-{3-cyano-4,6-dimethyl-1-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-[(4R)-2,2-dimethyltetrahydro-2H-pyran-4-yl]prop-2-enamide To a solution of (2E)-3-{3-cyano-4,6-dimethyl-1-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}prop-2-enoic acid (861 mg, 2.32 mmol) in THF (8 ml) were added DMF (0.10ml) and oxalylchloride (0.243 ml, 2.79 mmol), the mixture was stirred at room temperature for 1 hour and the solvent was distilled off under reduced pressure. The residue was added under ice-cooling to a solution of 2,2-dimethyltetrahydro-2H-pyran-4-ylamine (600 mg, 4.64 mmol), triethylamine (1.08 ml, 7.71 mmol) and THF (6 ml), the mixture was stirred under ice-cooling for 2 hours, the reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane : ethyl acetate = 2 : 1 to 1 : 1) to separate two kinds of diastereomers. Firstly eluted diastereomer: (2E)-3-{3-cyano-4,6-dimethyl-1-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-[(4S)-2,2-dimethyltetrahydro-2H-pyran-4-yl]prop-2-enamide yield 247 mg, yield (rate) 22.1%1H-NMR (CDCl3) delta: 1.24-1.40 (8H, m), 1.80-2.30 (6H, m), 2.59 (3H, s), 2.76 (3H, s), 2.90-3.23 (2H, m), 3.65-3.80 (2H, m), 4.19-4.24 (1H, m), 5.51 (1H, d, J = 8.0 Hz), 6.49 (1H, d, J = 7.5 Hz), 6.68-7.26 (7H, m). IR (KBr) cm-1; 3268, 2215, 1661, 1622, 1588, 1553, 1507, 1427, 1331, 1262, 1198, 735, 748. Later eluted diastereomer: (2E)-3-{3-cyano-4,6-dimethyl-1-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridin-2-yl}-N-[(4R)-2,2-dimethyltetrahydro-2H-pyran-4-yl]prop-2-enamide Yield (amount) 222 mg, yield (rate) 19.8%1H-NMR (CDCl3) delta: 1.20-1.36 (8H, m), 1.76-2.29 (6H, m), 2.59 (3H, s), 2.76 (3H, s), 2.90-3.16 (2H, m), 3.65-3.80 (2H, m), 4.19-4.23 (1H, m), 5.48 (1H, d, J = 7.8 Hz), 6.50 (1H, d, J = 8.1 Hz), 6.71-7.26 (7H, m). IR (KBr) cm-1; 3268, 2215, 1661, 1620, 1588, 1549, 1507, 1449, 1427, 1368, 1331, 1262, 1198, 750, 733.

25850-22-0, As the paragraph descriping shows that 25850-22-0 is playing an increasingly important role.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP1535922; (2005); 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.185815-59-2,4-Isobutyldihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Example 3(i?)-3-(2-(Cinnamyloxy)-2-oxoethyl)-5-methylhexanoic acid, (III) Procedure BQuinine (28.7g, 88mmol) was suspended in toluene (38OmL). Cinnamyl alcohol (15.5 g, 115mmol) was added and the reaction mixture was cooled to -35 0C. The solution of 3- isobutylglutaric anhydride (15.0 g, 88 mmol) in toluene (1OmL) was added during 15 min and the reaction mixture was stirred at -35 0C for 24 hours. Toluene solution was washed with 5% HCl (250 + 5OmL), and than extracted with 2% K2CO3 solution (1000 + 25OmL). Aqueous extracts were washed with EtOAc (3x10OmL), acidified to pH 1 with cone. HCl and extracted with diisopropylether (150 + 5OmL). Combined extracts were warmed to 35 0C and (S)-alpha- phenylethylamine (9.7 g, 80 mmol) was added, followed by seed crystals (10 mg). Mixture was stirred for 4 hours at 25 C and filtered to obtain 24.8 g of (5)-alpha-phenylethylamine salt of (/?)-3-(2- (cinnamyloxy)-2-oxoethyl)-5-methylhexanoic acid. The salt was suspended in toluene (15OmL) and stirred with 3% HCl (10OmL) until clear solution was obtained. The aqueous acidic solution was separated and organic layer was washed once again with 3% HCl (30 mL). Evaporation of toluene afforded 17.3 g (66%) of monoester as viscous yellowish oil. HPLC analysis on Chiralpak AS column, hexane/EtOH/TFA=95/5/0.1 revealed 90.7 % ee., 185815-59-2

The synthetic route of 185815-59-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PLIVA ISTRAZIVANJE I RAZVOJ D.O.O.; MCLEISH, Nicholas, Alistair, Maxwell; WO2008/9897; (2008); 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.344329-76-6,Tetrahydro-2H-pyran-4-carboxamide,as a common compound, the synthetic route is as follows.

Example 117 A mixture of Example B5 (66 mg, 0.508 mmol) in DCE (2 mL) was treated with oxalyl chloride (64 mg, 0.508 mmol), stirred at RT for 5 min, then warmed to 80¡ã C. for 45 min. The mixture was cooled to RT, added to a solution of DIEA (188 mg, 1.456 mmol) and Example A25 (100 mg, 0.339 mmol) in dioxane (4 mL) and stirred at RT for 3 h. The mixture was diluted with EtOAc, washed successively with satd. NaHCO3, 1N NaOH and brine, dried over Na2SO4, concentrated to dryness and purified via reverse-phase silica gel chromatography (MeCN/H2O with 0.1percent TFA). The pure fractions were partially evaporated under reduced pressure and the aqueous residue was neutralized with satd. NaHCO3 and extracted with EtOAc (3*). The combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford N-((4,6-dimethyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)tetrahydro-2H-pyran-4-carboxamide (29 mg, 19percent) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 10.95 (s, 1H), 10.86 (s, 1H), 8.33 (d, J=5.7 Hz, 1H), 8.25 (s, 1H), 7.95 (s, 1H), 7.84 (s, 1H), 7.11 (d, J=2.4 Hz, 1H), 6.51 (dd, J=5.7, 2.5 Hz, 1H), 3.90-3.85 (m, 2H), 3.84 (s, 3H), 3.30-3.27 (m, 2H), 2.73-2.65 (m, 1H), 2.18 (s, 3H), 2.10 (s, 3H), 1.74-1.68 (m, 2H), 1.65-1.55 (m, 2H); MS (ESI) m/z: 451.2 (M+H+).

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

Reference£º
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Kaufman, Michael D.; Patt, William C.; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Yates, Karen M.; US2014/275080; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics