Heterocyclic Building Blocks-Tetrahydropyrans

19752-84-2, Tetrahydro-2H-pyran-3-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Production Example 1Dihydro-2H-pyran-3(4H)-one To a mixture of oxalyl chloride (2.28 mL, 26.6 mmol) and dichloromethane (40 mL) was added a mixture of DMSO (3.78 mL, 53.2 mmol) and dichloromethane (20 mL) while stirring at -78 C., and the mixture was stirred at -78 C. for 30 minutes. After then adding to this mixture a mixture of tetrahydropyran-3-ol (synthesized according to the method described in Tetrahedron, 60, 10411-10418, 2004) (136 g, 13.3 mmol) and dichloromethane (20 mL) at -78 C., the resulting mixture was stirred at -78 C. for 30 minutes, after which triethylamine (11.1 mL, 79.8 mmol) was added and stirring was continued for 2 hours while slowly raising the temperature to 0 C.Brine and diethyl ether were added to the mixture, and after sufficient shaking, the organic layer was separated and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was then filtered, and the solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (1.62 g, 162 mmol).1H-NMR (CDCl3) delta: 2.07-2.14 (m, 2H), 2.54 (t, J=6.8 Hz, 2H), 3.82-3.88 (m, 2H), 4.03 (s, 2H)., 19752-84-2

The synthetic route of 19752-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Eisai R&D Management Co., Ltd.; US2011/86882; (2011); A1;,
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,873397-34-3

Treat a mixture of N-[1-(2,3-dihydro-1H-indol-5-yl)ethyl]-4-fluorobenzamide, Isomer 1 (Preparation 24A) (150 mg, 0.528 mmol), racemic tetrahydropyran-3-carboxylic acid (100 mg. 0.739 mmol) and N,N-diisopropylethylamine (0.277 mL, 1.58 mmol) in DCM (5.28 mL) with 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxid hexafluorophosphate (304 mg, 0.791 mmol). Stir at room temperature for 45 minutes. Dilute the reaction mixture with DCM. Add water and saturated aqueous sodium bicarbonate solution. Separate the layers and extract the aqueous layer twice with DCM. Pass the combined organic layer through a hydrophobic frit (ISOLUTE? phase separator cartridge) and concentrate the filtrate. Purify by silica gel column chromatography eluting with a gradient of 20-55percent acetone in hexanes to give the title compound (184 mg, 88percent) as a white solid. ES/MS (m/z): 397.2 (M+H).

As the paragraph descriping shows that 873397-34-3 is playing an increasingly important role.

Reference£º
Patent; Eli Lilly and Company; Bastian, Jolie Anne; Chen, Jiehao; Cohen, Jeffrey Daniel; Henry, James Robert; McMillen, William Thomas; Reaman, Bradley Earl; Rubio, Almudena; Sall, Daniel Jon; Zhao, Gaiying; (36 pag.)US2017/354641; (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.125552-89-8,4-(Bromomethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

A mixture of methyl 6-(2,6-difluoro-4-hydroxyphenyl)-5-fluoropicolinate (1.0 equiv.), 4-(bromomethyl)tetrahydro-2H-pyran (2.0 equiv.) and K2CO3 (4.0 equiv.) in DMF (0.20 M) was heated at 100 C. for 20 min in microwave. The reaction mixture was cooled off to rt and partitioned between EtOAc and H2O. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give methyl 6-(2,6-difluoro-4-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)-5-fluoropicolinate in 100% yield. LC/MS=382.0 (MH+), Rt=0.97 min., 125552-89-8

The synthetic route of 125552-89-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Burger, Matthew; Ding, Yu; Han, Wooseok; Nishiguchi, Gisele; Rico, Alice; Simmons, Robert Lowell; Smith, Aaron R.; Tamez, JR., Victoriano; Tanner, Huw; Wan, Lifeng; US2012/225061; (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.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

To a solution of (Z)-phenyl N’-cyano-N-(3,4-difluorophenyl)carbamimidate (286 mg, 1.05 mmol) and 2-(3-bromopropoxy)tetrahydro-2H-pyran (369 mg, 277 mu, 1.57 mmol) in DMF (10.5 mL) was added at room temperature under an athmosphere of nitrogen potassium carbonate (289 mg, 2.09 mmol). The suspension was heated to 85C over night. Additional 2-(3- bromopropoxy)tetrahydro-2H-pyran (140 mu, 0.8mmol) und potassium carbonate (145 mg, 1.05 mmol) was added and the reaction was heated for 5 hours to 85C. Water was added and the reaction was extracted twice with diethyl ether. The combined organic layers were washed with water and with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The title compound was obtained as a light yellow viscous oil (202 mg, 46%) after column chromatography on silica gel using a gradient of heptane/ethyl acetate 4: 1 to 1 : 1 (v/v) as eluent.MS ISP (m/e): 332.1 (100) [(M-THP+H)+], 416.3 (5) [(M+H)+].1H NMR (DMSO-D6, 300 MHz): delta (ppm) = 7.38 (t, 2H), 7.26 – 7.16 (m, 3H), 7.05 (m, 3H), 4.52 (t, 1H), 3.97 (t, 2H), 3.85 (m, 2H), 3.48 (m, 2H), 2.00 (pent, 2H), 1.79 (m, 1H), 1.68 (m, 1H), 1.55 (m, 4H)).

33821-94-2, 33821-94-2 2-(3-Bromopropoxy)tetrahydro-2H-pyran 2777988, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; BAUMANN, Karlheinz; GOETSCHI, Erwin; GREEN, Luke; JOLIDON, Synese; KNUST, Henner; LIMBERG, Anja; LUEBBERS, Thomas; THOMAS, Andrew; WO2011/92272; (2011); 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

Example 78 Preparation of 5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid [(S)-2,5-dioxo-1-(tetrahydro-pyran-4-ylmethyl)-pyrrolidin-3-yl]-amide Step1: Compound 75c (200 mg, 0.93 mmol), 60a (201 mg, 1.12 mmol), KI (163 mg, 0.98 mmol), K2CO3 (644 mg, 4.67 mmol) and acetonitrile (20 mL) were mixed in a microwave vial. The resulting mixture was reacted under microwave condition at 140 C. for 1 h. After being cooled, the mixture was filtered. The filtrate was evaporated and the residue was purified by column chromatography (EA::PE=1:3) to provide 78a(224 mg, 77%).

125552-89-8, As the paragraph descriping shows that 125552-89-8 is playing an increasingly important role.

Reference£º
Patent; Xcovery, Inc.; US2009/76005; (2009); 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

[00547] Step B: To a mixture of tert-butyl ethyl(1-((1s,4s)-4-((1-methyl-6-oxo-1,6-dihydropyridazin-3-yl)oxy)cyclohexyl)-3-(1H-pyrazol-3-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (0.022 g, 0.041 mmol) and 4-(Bromomethyl)tetrahydropyran (0.015 g, 0.082 mmol) in DMA (0.4 mL) was added Cs2CO3 (0.028 g, 0.086 mmol) and the reaction was heated to 100 C. After 3 h, the reaction was cooled to room temperature and DCM (2 mL) was added and then TFA (5 mL) added. After 1 hr, the reaction mixture was concentrated and the resultant oil was resuspended in 1 mL of a solution of 60:40 ACN:water with 2% TFA modifier. The product was purified by C-18 HPLC (5-60% ACN in water with 0.2% TFA modifier). The product fractions were partitioned between aqueous NaHCO3 and DCM, extracted with DCM (2×15 mL), washed with brine (15 mL), dried over Na2SO4, filtered and concentrated to afford 6-(((1s,4s)-4-(6-(ethylamino)-3-(1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrazol-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)cyclohexyl)oxy)-2-methylpyridazin-3(2H)-one (0.0087 g, 0.015 mmol, 37 % yield) as a solid. Mass spectrum (apci) m/z = 533.2 (M+H). 1H NMR (CDCl3) delta 9.08 (s, 1H), 7.42 (d, J = 2.2 Hz, 1H), 7.02 (d, J = 9.8 Hz, 1H), 6.94 (d, J = 9.8 Hz, 1H), 6.78 (d, J = 2.4 Hz, 1H), 6.08 (s, 1H), 5.10 (m, 1H), 4.32 (tt, J = 11.5, 3.9 Hz, 1H), 4.07 (d, J = 7.2 Hz, 2H), 3.97 (m, 2H), 3.66 (s, 3H), 3.43-3.26 (m, 4H), 2.53-2.40 (m, 2H), 2.38-2.20 (m, 3H), 1.97-1.89 (m, 2H), 1.84-1.73 (m, 2H), 1.59-1.51 (m, 2H), 1.45-1.33 (m, 5H).

125552-89-8, The synthetic route of 125552-89-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BOYS, Mark Laurence; COOK, Adam; GAUDINO, John; HINKLIN, Ronald Jay; LAIRD, Ellen; MCNULTY, Oren T.; METCALF, Andrew T.; NEWHOUSE, Brad; ROBINSON, John E.; (545 pag.)WO2019/113190; (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.40191-32-0,Tetrahydro-2H-pyran-4-carbonyl chloride,as a common compound, the synthetic route is as follows.,40191-32-0

Example 57 {(S)-3-[6-(6-Amino-5-trifluoromethyl-pyridin-3-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy]-pyrrolidin-1-yl}-(tetrahydro-pyran-4-yl)-methanone (0915) To a solution of (S)-tert-butyl 3-(6-(6-(bis(tert-butoxycarbonyl)amino)-5-(trifluoromethyl)pyridin-3-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yloxy)pyrrolidine-1 (120 mg, 0.18 mmol) in CH2Cl2 (2.0 mL), was added TFA (2.0 mL) and the mixture stood at rt for 1 h. Concentrated in vacuo and eluted through an Isolute SCX-2 cartridge, eluting with methanol, then with 2M ammonia in methanol. Basic fractions were concentrated in vacuo to give 5-[4-((S)-pyrrolidin-3-yloxy)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-3-(trifluoromethyl)pyridin-2-yl)amine (61 mg, 90% yield). 5-[4-((S)-pyrrolidin-3-yloxy)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-3-(trifluoromethyl)pyridin-2-yl)amine (30 mg, 0.079 mmol) was dissolved in CH2Cl2 (2.0 mL) and was added simultaneously portionwise with sat.NaHCO3(aq) (2.0 mL) to a vigorously stirring solution of tetrahydro-2H-pyran-4-carbonyl chloride (15 mg, 0.10 mmol) in CH2Cl2 (2.0 mL) at rt. The resulting biphasic mixture was stirred at rt for 1 h. Diluted with CH2Cl2 (10 mL) and the organic layer was separated by filtering through a phase separation tube and concentrated in vacuo. Purification by reverse phase Gilson HPLC (Method A) and subsequent neutralization of the combined fractions by elution through an Isolute SCX-2 cartridge, eluting with methanol, then with 2M ammonia in methanol. Basic fractions were concentrated in vacuo to give {(S)-3-[6-(6-amino-5-trifluoromethyl-pyridin-3-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy]-pyrrolidin-1-yl}-(tetrahydro-pyran-4-yl)-methanone as a pale yellow powder (19 mg, 50% yield) 1H NMR (400 MHz, CDCl3, 298K) delta ppm 1.56-1.72 (m, 2H) 1.87-2.03 (m, 2H) 2.23-2.74 (m, 3H) 3.04-3.14 (m, 2H) 3.48-4.13 (m, 12H) 5.15-5.43 (m, 2H, Ar-NH2) 5.73-5.79 (m, 1H) 7.55-7.64 (m, 1H) 7.93-8.02 (m, 1H) 8.61-8.67 (m, 1H) LCMS: [M+H]+=397.1, Rt(3)=1.32 min.

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

Reference£º
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; US2015/342951; (2015); 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 a solution of N-(2-hydroxyethyl)-4-(2H-tetrazol-5-yl)benzenesulfonamide (200 mg, 0.743 mmol, Intermediate 17) in Lambda/,/V-dimethylformamide (10 ml_), potassium carbonate (205 mg, 1 .485 mmol, commercial source: RCP) was added followed by the addition of 4- (bromomethyl)tetrahydro-2H-pyran (159 mg, 0.88 mmol, commercial source: Aldrich) at 26 C. The reaction mixture was heated to 80 C for 8 h. Upon completion, the reaction mixture was cooled to 26 C and evaporated under reduced pressure. The crude was purified by column chromatography (silicagel 100-200 mesh), eluted with 5% methanol in dichloromethane. The pure fractions were concentrated under reduced pressure to afford N- (2-hydroxyethyl)-4-(2-((tetrahydro-2H-pyran-4-yl)methyl)-2H-tetrazol-5- yl)benzenesulfonamide (80 mg, 18%).1H NMR (400 MHz, DMSO-de) delta 8.28-8.24 (m, 2H), 7.98 (d, J = 8.6 Hz, 2H), 7.79-7.72 (m, 1 H), 4.73-4.65 (m, 3H), 3.88-3.80 (m, 2H), 3.38 (q, J = 6.1 Hz, 2H), 3.29-3.27 (m, 2H), 2.85 (q, J = 5.3 Hz, 2H), 2.35-2.23 (m, 1 H), 1.52-1.46 (m, 2H), 1.40-1.31 (m, 2H). MS m/z [M+H]+= 368.12.

125552-89-8, As the paragraph descriping shows that 125552-89-8 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ALEMPARTE-GALLARDO, Carlos; ENCINAS, Lourdes; ESQUIVIAS PROVENCIO, Jorge; (206 pag.)WO2019/34729; (2019); 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

Step a) Intermediate 204 l-(4-Bromophenyl)-N-methyl-N-(tetrahydro-2H-pyran-4-yl)methanesulfonamide To a suspension of N-methyltetrahydro-2H-pyran-4-amine (0.507 g, 4.40 mmol) and sodium carbonate (0.467 g, 4.40 mmol) in MeCN (10 ml) was added (4- bromophenyl)methanesulfonyl chloride (0.593 g, 2.201 mmol) and the reaction mixture was stirred at r.t. for 1.5 h. The mixture was quenched with water and extracted with EtOAc (x 2). The organics were dried (MgS04) and concentrated under reduced pressure to yield l-(4-bromophenyl)-N-methyl-N-(tetrahydro-2H-pyran-4- yl)methanesulfonamide as a white solid (0.634 g, 83 %). ? NMR (400 MHz, MeOD) delta 7.56 (m, 2H, J = 8.34 Hz), 7.38 (m, 2H, J = 8.34 Hz), 4.34 (s, 2H), 3.95 (dd, 2H, J = 1 1.62, 4.55 Hz), 3.69 – 3.82 (m, 1H), 3.35 – 3.43 (m, 2H), 2.72 (s, 3H), 1.74 – 1.87 (m, 2H), 1.45 – 1.53 (m, 2H), 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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; RUPRAH, Parminder, Kaur; MERCHANT, Kevin, John; WALSH, Louise, Marie; KERR, Catrina, Morven; FIELDHOUSE, Charlotte; HARRISSON, David; MAINE, Stephanie; HAZEL, Katherine; WO2013/27001; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

40191-32-0, Tetrahydro-2H-pyran-4-carbonyl chloride is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

N,O-Dimethylhydroxylamine hydrochloride (1.23 g, 12.7 mmol) and N-methyl morpholine (3.80 mL, 34.5 mmol) were dissolved in DCM (20 mL) and a solution of oxane-4-carbonyl chloride (1.71 g, 11.5 mmol) in DCM (20 mL) was added drop-wise. The reaction mixture was stirred for 2 h, then diluted to 200 mL with DCM, washed with 1 M aq HCl (2*100 mL), 1M aq Na2CO3 (100 mL) and water (100 mL), dried (MgSO4) and concentrated in vacuo to give the crude title compound as a yellow oil (1.87 g, 94%). LCMS (ES+): 174.1 [MH]+.

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

Reference£º
Patent; PROXIMAGEN LIMITED; Evans, David; Carley, Allison; Stewart, Alison; Higginbottom, Michael; Savory, Edward; Simpson, Iain; Nilsson, Marianne; Haraldsson, Martin; Nordling, Erik; Koolmeister, Tobias; US2014/357623; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics