Tag: M.W:100-200

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

To a solution of Intermediate 227A (32.6 mg, 0.06 mmol) in THF (1 mL) was added tetrahydro-2H-pyran-3-ol (61.3 mg, 0.600 mmol) and KHDMS (0.120 mL, 1M,0.120 mmol). The mixture was stirred at room temperature for 1 hour. TLC and LCMS indicated completion of the reaction. The reaction was quenched with iN HC1, extracted with EtOAc, the combined organic layer was washed with saturated sodium bicarbonate, brine, dried over sodium sulfate and concentrated. The compound was dissolved in DMSO and purified via preparative LC/MS (Method D: Gradient: 45-90% B over 20minutes, then a 5-minute hold at 100% B). Fractions containing the desired product were combined and dried via centrifugal evaporation to Example 234 (1.6 mg, 3.00 imol, 5.00 % yield). ?H NMR (500MHz, DMSO-d6) 8.67 (s, 1H), 8.52 (s, 1H), 7.86 (d, J8.9 Hz, 1H), 7.77 (s, 1H), 7.72-7.42 (m, 2H), 7.02 (d, J=8.8 Hz, 1H), 5.02 (br. s., 1H), 4.49 (br. s., 1H), 4.04 (s, 3H), 3.53-3.41 (m, 3H), 3.34 (br. s., 2H), 3.18-3.09 (m, 1H), 2.59 (s,3H), 1.83 (br. s., 1H), 1.66 (br. s., 1H), 1.57 (br. s., 1H), 1.42 (br. s., 1H). LC-MS:method L, RT = 2.32 mm, MS (ESI) m/z: 507.30 (M+H)t Analytical HPLC purity (method B): 95%., 19752-84-2

As the paragraph descriping shows that 19752-84-2 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; HALPERN, Oz Scott; JIANG, Wen; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (545 pag.)WO2018/13776; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4295-99-2,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.

Three-neck flask equipped with mechanical stirrer, thermometer, dropping funnel, 250ml of water was added to the flask, stirring was added 4-cyano-tetrahydropyran 111.14g (1mole), cooled to 0 ~ 5 ¡ã C, was added at a concentration of 10 minutes 13.8percent sodium hydroxide solution, a total of 290 g (1 mole), temperature controlled at 0 ~ 10 ¡ã C, after each addition incubated for 15 to 20 minutes, all the alkali was added, stirred for 1 to 3 hours, the reaction was complete by gas detecting material, controlling the temperature of 0 ~ 5 ¡ã C, was slowly added to a concentration of 10percent sodium hypochlorite solution 1116.6g (1.5mole), plus Bi, 0 ~ 5 ¡ã C for 1 hour, heated at reflux temperature for 2 hours to complete the reaction intermediate vapor detection, water cooling to 10 ~ 40 ¡ã C, with 500ml dichloromethane and 50ml methanol solvent mixture and extracted 3 times, the combined extracts were recovered by distillation of methylene chloride, methylene chloride was distilled off to make, distillation to give 4-amino-tetrahydropyran 75.3 g, with a purity of 99.1percent, a yield of 73.7percent.

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

Reference£º
Patent; Qingdao Frontierchem Co.,Ltd; Wang, yuchen; Liu, guihong; Li, XIAOYAO; Liu, Guo Chao; (5 pag.)CN102993144; (2016); B;,
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 3-Methyl-6-[2-(tetrahydropyran-2-yloxy)ethyl]-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione 40 g of ethyldiisopropylamine and 52.5 g of 2-(2-chloroethoxy)tetrahydropyran (96% pure according to GC) were added to 54.5 g of 3-methyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione in 1.5 l of dimethylformamide, with stirring, and the mixture was heated for 30 h at 70 C. It was concentrated under vacuum, the residue was worked up by extraction with dichloromethane and water and the combined dichloromethane phases were dried and concentrated to give 25 g of 3-methyl-6-[2-(tetrahydropyran-2-yloxy) ethyl]-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione, which was purified by bulb-tube distillation at a bath temperature of 80 C. and 0.1 mbar and by column chromatography on aluminum oxide (activity grade III) and elution with dichloromethane/ethanol (volume ratio 95:5). 6-(2-Hydroxyethyl)-3-methyl-5,6,7,8-tetrahydro-1H-pyrido[4,3-d]pyrimidine-2,4-dione, 5631-96-9

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

Reference£º
Patent; Hoechst Aktiengesellschaft; US5556854; (1996); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

388109-26-0, Ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

388109-26-0, Step 1:To a solution of ethyl 3-oxotetrahydro-2H-pyran-4-carboxylate (1.0 g, 5.81 mmol) in DCM (30 mL) was added DIPEA (1.22 mL, 6.97 mmol) and Tf2O (1.08 mL, 6.39 mmol) at -78 C., then it was warmed up to room temperature and stirred at room temperature for 2 h, the solution was diluted with DCM, washed with Sat. NaHCO3, brine, dried and concentrated to give ethyl 5-(((trifluoromethyl)sulfonyl)oxy)-3,6-dihydro-2H-pyran-4-carboxylate as crude product (2 g).

The synthetic route of 388109-26-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; Metcalf, Brian W.; (29 pag.)US9248199; (2016); 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.25850-22-0,2,2-Dimethyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.

Production Example 321 (0641) 5-Benzyloxymethylisoxazole-3-carboxylic acid (0.24 g, 1.0 mmol), 4-amino-2,2-dimethyltetrahydropyran (0.18 ml, 1.2 mmol) and 1-hydroxybenzotriazole (0.01 g, 0.1 mmol) were added to chloroform (amylene addition product) (2.5 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.24 g, 1.2 mmol) was added to the mixture at room temperature, and the mixture was stirred overnight. Then, dilute hydrochloric acid was added thereto, and the mixture was extracted twice with chloroform. The organic layer was passed through a short column to remove impurities, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 0.29 g of N-(2,2-dimethyltetrahydropyran-4-yl)-5-benzyloxymethylisoxa zole-3-carboxamidc: (hereinafter, referred to as Compound of Present Invention (335)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)):1.26(3H, s), 1.29(3H, s), 1.33-1.40(1H, m), 1.41-1.52(1H, m), 1.89-2.00(2H, m), 3.72-3.84(2H, m), 4.27-4.38(1H, m), 4.61(2H, s), 4.65(2H, s), 6.62(1H, br s), 6.72(1H, s), 7.30-7.40(5H, m)

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

Reference£º
Patent; Sumitomo Chemical Company, Limited; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (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.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

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.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

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.4295-99-2,4-Cyanotetrahydro-4H-pyran,as a common compound, the synthetic route is as follows.,4295-99-2

Example 9ii (3-BromophenyI)(tetrahydro-2H-pyran-4-yI)methanimine 1,3-Dibromobenzene (3.04 mL, 25.2 mmol) was dissolved in Et2O (60 mL) and cooled to – 78 0C. n-Butyllithium (10.1 mL, 25.25 mmol) was added and the the solution stirred for 30 min. Tetrahydro-2H-pyran-4-carbonitrile (2.80 g, 25.20 mmol) was added in Et2O (20 mL) is at -78 0C and the reaction was stirred for 30 min. The reaction was then allowed to warm to room temperature over 30 min. MeOH (20 mL) containing ammonium acetate (2 g, 25.95 mmol) was added. The solvents were evaporated and the residue taken up in DCM and water. The organic layer was separated and the aqueous phase extracted with DCM. The combined organic phases were shaken with brine and dried over MgSO4. The mixture was20 filtered and the solvent evaporated to yield 4.64 g (69% yield) of the title compound: MS (ES+) m/z 268, 270 [M+H]+.

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

Reference£º
Patent; ASTRAZENECA AB; BLID, Jan; GINMAN, Tobias; GRAVENFORS, Ylva; KARLSTROeM, Sofia; KIHLSTROeM, Jacob; KOLMODIN, Karin; LINDSTROeM, Johan; RAHM, Fredrik; SUNDSTROeM, Marie; SWAHN, Britt-Marie; VIKLUND, Jenny; VON BERG, Stefan; VON KIESERITZKY, Fredrik; WO2011/2408; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics