Heterocyclic Building Blocks-Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1240390-36-6,tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

Step 2 {(3R,4R)-4-[7-(Naphthalene-2-ylcarbamoyl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester To a solution of 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid naphthalene-2-ylamide (0.0792 g, 0.233 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (0.0756 g, 0.350 mmol) in dioxane (3 mL) was added diisopropylethylamine (0.122 mL, 0.699 mmol). The reaction mixture was heated at 120 C. overnight. The reaction mixture was cooled and then diluted with dichloromethane, washed with aqueous sodium carbonate, then brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue obtained was then purified by chromatography (silica, 40 g, 0 to 60% ethyl acetate in hexanes) to give {(3R,4R)-4-[7-(naphthalene-2-ylcarbamoyl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (0.063 g, 0.121 mmol, 52%) as a yellow solid. LCMS m/z [M+H]=520.

1240390-36-6, 1240390-36-6 tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate 68077633, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Hoffmann-La Roche Inc.; Chen, Shaoqing; Hermann, Johannes Cornelius; Le, Nam T.; Lucas, Matthew C.; Padilla, Fernando; US2013/178460; (2013); 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.101691-65-0,(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

A solution of 5-bromo-2-chloropyridin-3-amine (1.3 g, 6.27 mmol) in DMF (20 ml_) was added slowly sodium hydride (60 wt.% in mineral oil, 0.301 g) was stirred for 20 min, followed by addition of (tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate (1.694 g, 6.27 mmol). The resulting reaction mixture was stirred at room temperature for 58 hrs, diluted with EtOAc, washed with water, brine, dried over sodium sulphate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, EtOAc/hexane = 22/78) providing 5-bromo-2-chloro-N- ((tetrahydro-2H-pyran-4-yl)methyl)pyridin-3-amine (1.27 g). LCMS (m/z): 305.0 [M+H]+; Rt = 0.89 min.

101691-65-0, As the paragraph descriping shows that 101691-65-0 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; NG, Simon C.; PFISTER, Keith B.; SENDZIK, Martin; SUTTON, James; WO2012/101063; (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.14774-37-9,Tetrahydropyran-4-methanol,as a common compound, the synthetic route is as follows.

Step 2 Under an argon atmosphere, (tetrahydropyran-4-yl)-methanol (14.01 g, 120.6 mmol) was dissolved in dichloromethane (241 mL), and triethylamine (50.44 mL, 361.8 mmol) was added thereto under ice-cooling, and then, methanesulfonyl chloride (11.21 mL, 144.7 mmol) was slowly added dropwise thereto at 10C or lower. After the dropwise addition was completed, the mixture was stirred at room temperature for 2 hours. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was reslurried in hexane to give (tetrahydropyran-4-yl)methylmethanesulfonate (20.51 g, 105.6 mmol, yield: 87%). 1H-NMR (dppm, CDCl3) : 4.07 (d, J = 6.6 Hz, 2H), 4.00 (dd, J = 11.8, 2.2 Hz, 2H), 3.40 (dt, J = 11.8, 2.2 Hz, 2H), 3.02 (s, 3H), 2.10-1.96 (m, 1H), 1.69-1.63 (m, 2H), 1.47-1.32 (m, 2H). Mass (m/e): 195 (M+H)+, 14774-37-9

As the paragraph descriping shows that 14774-37-9 is playing an increasingly important role.

Reference£º
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2090570; (2009); 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.5631-96-9,2-(2-Chloroethoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A reaction vessel is charged with N-Boc 4-hydroxyl-5?-spiro-thalidomide (1 equiv.), potassium carbonate (2 equiv.) and DMF (0.5 M). 2-(2-chloroethoxy)tetrahydro-2H-pyran (1.1equiv.) is added and the reaction is heated at 110 C for 12 hours. The reaction is then cooled to ambient temperature and concentrated. The residue is taken up in water and ethyl acetate and the layers separated. The aqueous layer is extracted with ethyl acetate (2 x). The combined organic layer is washed with brine, dried over sodium sulfate, filtered and concentrated. The crude residue is used directly in the following reaction.A reaction vessel is charged with crude residue (1 equiv.), MeOH and DCM (1:1, 0.2 M). p-Toluenesulfonic acid (0.1 equiv.) is added and the reaction mixed at ambient temperature. Upon completion of the hydrolysis reaction, the volatiles are removed by rotary evaporation and the residue purified by silica gel chromatography to provide tert-butyl 7-(4-(2-hydroxyethoxy)-1,3- dioxoisoindolin-2-yl)-4,6-dioxo-5-azaspiro[2. 5]octane-5-carboxylate., 5631-96-9

As the paragraph descriping shows that 5631-96-9 is playing an increasingly important role.

Reference£º
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; FITZGERALD, Mark, E.; MICHAEL, Ryan, E.; (790 pag.)WO2017/197056; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

185815-59-2, 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 3: Preparation of 3-aminomethyl-N,N-diethyI-5-methylhexanamide.; Step a): Preparation of 3-(2-(diethyl amino)-2-oxoethyl)-methylhexanoic acid; To a solution of 3- isobutyl glutaric anhydride (5 grams) in dichloromethane(10 ml), added diethyl amine (4.3 grams) and stirred the reaction mixture for 12 hrs at 250C. The reaction mixture was quenched with water (10 ml) and the pH of the reaction mixture adjusted to 1.0 using hydrochloric acid. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The organic layers were combined and the solvent distilled off to provide the title compound as a residue. Yield: 6.5 grams, 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; SATYANARAYANA REDDY, Manne; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; SATYANARAYANA, Revu; WO2009/1372; (2008); A2;,
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.4677-20-7,4-(2-Bromoethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.

(rac)-Ethyl 4-chloro-3-ethyl-7-{3-[(6-fluoronaphthalen-1 -yl)oxy]propyl}-2-methyl- 10,11 ,12,13,14,15-hexahydro-2H-pyrazolo[3′,4′:8,9][1 ,6]diazacycloundecino[10,11 ,1 -hi]indole- 8-carboxylate (see Intermediate 115, 50.0 mg, 81.0 pmol), 4-(2-bromoethyl)oxane (17.2 mg, 89.1 pmol) and cesiumcarbonate (132 mg, 405 pmol) were dissolved in 410 mI_ DMF and the reaction mixture was stirred at 600 in a sealed ve ssel under nitrogen atmosphere. The reaction mixture was diluted with water and dichloromethane, stirred for a few minutes, filtered through a silicone coated filter and concentrated under reduced pressure. The crude product was purified by HPLC chromatography under basic conditions to provide the target compound in 99% purity: 23 mg. LC-MS (Methode 2): Rt = 1.85 min; MS (ESIpos): m/z = 730 [M+H]+ 1 H-NMR (400MHz, DMSO-d6): d [ppm]= 0.55 – 0.74 (m, 1 H), 0.75 – 0.96 (m, 7H), 1.00 – 1.13 (m, 3H), 1.13 – 1.32 (m, 7H), 1.83 – 1.93 (m, 2H), 2.03 – 2.27 (m, 4H), 2.35 – 2.47 (m, 2H), 2.88 (td, 1 H), 2.97 (d, 1 H), 3.19 – 3.31 (m, 2H), 3.50 (br d, 1 H), 3.59 (br dd, 1 H), 3.72 – 3.93 (m, 5H), 4.04 – 4.16 (m, 1 H), 4.17 – 4.39 (m, 4H), 6.90 (dd, 1 H), 7.24 (d, 1 H), 7.37 – 7.50 (m, 3H), 7.67 (dd, 1 H), 7.75 (d, 1 H), 8.30 (dd, 1 H). As side product of the reaction to Intermediate 202the target compound was isolated in 98% purity: 12 mg. LC-MS (Methode 2): Rt = 1.77 min; MS (ESIpos): m/z = 774 [M+H]+ 1 H-NMR (400MHz, DMSO-d6): d [ppm]= 0.83 (t, 3H), 0.91 (br d, 2H), 0.98 – 1.17 (m, 4H), 1.18 – 1.31 (m, 5H), 1.32 – 1.56 (m, 5H), 2.13 – 2.31 (m, 4H), 3.08 – 3.31 (m, 4H), 3.75 (br dd, 2H), 3.80 – 3.98 (m, 6H), 3.99 – 4.35 (m, 5H), 4.36 – 4.53 (m, 2H), 6.86 (dd, 1 H), 7.25 (br d, 1 H), 7.34 – 7.49 (m, 3H), 7.66 (dd, 1 H), 7.80 (d, 1 H), 8.24 (dd, 1 H).

4677-20-7, As the paragraph descriping shows that 4677-20-7 is playing an increasingly important role.

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; THEDE, Kai; MENGEL, Anne; CHRIST, Clara; KUHNKE, Joachim; JOHANNES, Sarah, Anna, Liesa; BUCHGRABER, Philipp; KLAR, Ulrich; SACK, Ulrike; KAULFUSS, Stefan; FERNANDEZ-MONTALVAN, Amaury, Ernesto; WERBECK, Nicolas; MOeNNING, Ursula; NOWAK-REPPEL, Katrin; LEMKE, Chris; SERRANO-WU, Michael, H.; MCKINNEY, David; FITZGERALD, Mark; NASVESCHUK, Christopher; LAZARSKI, Kiel; FERRARA, Steven, James; FURST, Laura; WEI, Guo; MCCARREN, Patrick, Ryan; HARVEY, Rebecca, Ann; PAYNE, Daniel; PESNOT, Thomas; WILSON, Craig; (683 pag.)WO2019/96905; (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.1240390-36-6,tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

Step 2 {(3R,4R)-4-[7-(4,6-Dimethyl-pyridin-2-ylcarbamoyl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester To a solution of 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (4,6-dimethyl-pyridin-2-yl)-amide (0.149 g, 0.466 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (0.121 g, 0.559 mmol) in dioxane (4 mL) was added diisopropylethylamine (0.244 mL, 1.4 mmol). The reaction mixture was heated at 120 C. overnight. The reaction mixture was cooled and then diluted with dichloromethane, washed with aqueous sodium carbonate, then brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue obtained was then purified by chromatography (silica, 40 g, 0 to 15% EtOAc in hexanes) to give {(3R,4R)-4-[7-(4,6-dimethyl-pyridin-2-ylcarbamoyl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (0.104 g, 0.209 mmol, 44.8%) as a yellow solid. LCMS m/z [M+H]=499.

1240390-36-6, The synthetic route of 1240390-36-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Hoffmann-La Roche Inc.; Chen, Shaoqing; Hermann, Johannes Cornelius; Le, Nam T.; Lucas, Matthew C.; Padilla, Fernando; US2013/178460; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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

Example 1D 5-amino-2H-pyran-3(6H)-one The crude product from Example 1C (33 g) was treated with ethanol (800 mL) and concentrated sulfuric acid (0.2 mL), heated to reflux for 2 hours, cooled to 0 C., treated with methanol saturated with ammonia (200 mL), stirred at ambient temperature for 4 hours and concentrated. The residue was purified by flash chromatography over silica gel (2% and then 5% and then 10% methanol/methylene chloride) to provide the title compound (5 g). MS (DCI/NH3)m/z 114 (M+H)+, 131 (M+NH4)+; 1H NMR (DMSO-d6) delta3.80 (s, 2H), 4.19 (s, 2H), 5.01 (s, 1H), 7.01 (bs, 2H)., 61363-56-2

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; Altenbach, Robert J.; Rotert, Gary A.; Carroll, William A.; Gopalakrishnan, Murali; Molinari, Eduardo Jose Vicente; Davis-Taber, Rachel A.; Scott, Victoria Eleanor Sarah; US2003/65182; (2003); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

141095-78-5, 2-Bromo-1-(tetrahydro-2H-pyran-4-yl)ethanone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 1-methyl-2-pyrrolidone (2.0 mL) solution of the compound (41 mg) obtained by the technique of Reference Example 37, N,N?-carbonyldiimidazole (21 mg) was added, and the resultant was stirred at room temperature for 1 hour. Then, pyrazin-2-amine (14 mg) was added thereto, and the resultant was stirred at room temperature for 1 hour, then at 100 C. for 3.5 hours, then overnight at room temperature, and further at 100 C. for 7.5 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution, followed by extraction with chloroform. An organic layer was separated using a phase separator, and the solvent was distilled off under reduced pressure. The obtained residue was purified by preparative LC to obtain the title compound (2.5 mg) as a pale yellow oil.MS (ESI-APCI): 373[M+H]+1H NMR (600 MHz, CHLOROFORM-d) deltappm 1.15-1.25 (6H, m), 2.17-2.24 (6H, m), 2.99 (3H, s), 3.01-3.24 (3H, m), 3.25-3.69 (4H, m), 4.22 (2H, s), 6.58 (1H, s), 7.01 (1H, s), 7.43 (1H, br. s.), 7.67 (1H, s)

141095-78-5, The synthetic route of 141095-78-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TOYAMA CHEMICAL CO., LTD.; TAISHO PHARMACEUTICAL CO., LTD.; Tanikawa, Tetsuya; Ushiki, Yasunobu; Ushiyama, Fumihito; Yamaguchi, Toru; Ono, Naoya; Yamamoto, Keiko; Tsuruta, Risa; Tsutsui, Yasuhiro; Fujino, Noritomo; Mori, Ayumu; US2014/155597; (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.110238-91-0,Methyl tetrahydro-2H-pyran-4-carboxylate,as a common compound, the synthetic route is as follows.

Ammonium hydroxide (1 L) was added to a solution of methyl tetrahydropyranyl acetate (20 mL, 150 mmol) in methanol (500 mL), and the reaction was stirred overnight at ambient temperature. Additional ammonium hydroxide (500 mL) was added, and the reaction was stirred for four additional days. The methanol was removed under reduced pressure. Solid sodium chloride was added to the aqueous layer, which was extracted with chloroform (3 x 150 mL). The combined extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 11.4 g of tetrahydropyran-4- carboxamide as a white solid., 110238-91-0

The synthetic route of 110238-91-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2004/58759; (2004); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics