Tag: M.W:100-200

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

N-Methyl-N-(tetrahydro-2H-pyran-4-yl)amine At -70 C., 170 g (5.5 mol) of gaseous methylamine were introduced into 1.5 l of methanol. The solution was admixed dropwise with 100 g (1 mol) of sulfuric acid. 100 g (1 mol) of tetrahydro-4H-pyran-4-one and 36.4 g (0.6 mol) of sodium borocyanohydride were added in succession, and the mixture was stirred at room temperature for 3 days, resulting in a white precipitate. The solution was filtered and the filtrate was distilled. B.p. 56-58 C. (12 mm), yield 96 g. 1H NMR (270 MHz, in CDCl3): delta=1.30 (s, 1H), 1.38 (dq, 2H), 1.85 (dd, 2H), 2.43 (s, 3H), 2.57 (tt, 1H), 3.41 (dt, 2H), 3.99 (dt, 2H)., 29943-42-8

As the paragraph descriping shows that 29943-42-8 is playing an increasingly important role.

Reference£º
Patent; BASF Aktiengesellschaft; US6277790; (2001); B1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

127956-11-0, Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

127956-11-0, A mixture of crude 4-oxo-tetrahydro-pyran-3-carboxylic acid methyl ester (1780 g, 1 1 mol) and triethylamine (830 g, 8.2 mol) in MeOH (3560 mL) was cooled to 0C under N2. A solution of 2-chloro-acetamidine (567 g, 4.4 mol) in 890 mL of MeOH was added dropwise over 50 minutes. The reaction mixture was stirred at 0C for 30 minutes and then at about 20C for 16 hours. LCMS at 215nm and TLC (DCM:MeOH=10:1) analysis showed that most of 4-oxo-tetrahydro-pyran-3-carboxylic acid methyl ester was consumed. The mixture was then filtered and concentrated to give black oil, which was subsequently purified by flash column chromatography on silica gel and eluted with DCM to give yellow solid/oil mixture, which was further triturated with MTBE (-1200 mL) and H20: CH3CN: EA=1 :1 :2 (-600 mL) to give the title compound as a white solid (318 g). MS m/z 201 .2 (M+H). CHN analysis: calculated (results). C 47.89 (47.95), H 4.52 (4.401), N 13.96 (13.76).

As the paragraph descriping shows that 127956-11-0 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; CHEN, Christine Hiu-Tung; CHIN, Noel Chin; DIPIETRO, Lucian V.; FAN, Jianme; PALERMO, Mark G; SHULTZ, Michael David; TOURE, Bakary-Barry; WO2013/8217; (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.7525-64-6,4-Methyltetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

7525-64-6, To a suspension of sodium hydride, 60% in mineral oil (207 mg, 5.17 mmol) in THF (20 mL) was added 4-methyltetrahydro-2H-pyran-4-ol (500 mg, 4.30 mmol) at 0 C. After stirring 30 min, the solution was transferred to a solution of di(pyridin-2-yl)carbonate (931 mg, 4.30 mmol) in THF (20 mL) through a cannula. The formed slurry was stirred at 0 C. for 30 min. The slurry was warmed to rt and stirred for 2 h. At room temperature, to the reaction mixture was added sat. aq. NH4Cl (1 mL) upon which brief and significant effervescence was observed. The mixture was transferred to a 250 mL separatory funnel and was diluted with Et20 (50 mL). The solution was washed with water:brine (25 mL: 25 mL). The aq. phase was extracted with EtOAc (100 mL). The combined organics were dried over MgSO4; filtered; then concentrated in vacuo. The resulting residue was dissolved in acetone and then concentrated onto Celite in vacuo. The resulting powder was subjected to SiO2 purification on the Biotage system [90 g SiO2column, hexanes:EtOAc 90:10 to 60:40 over 8 CV] to get the product as a clear oil.1H NMR (400 MHz, CHLOROFORM-d) delta 8.48-8.39 (m, 1H), 7.87-7.76 (m, 1H), 7.30-7.24 (m, 2H), 7.16-7.09 (m, 1H), 3.83-3.69 (m, 4H), 2.29-2.16 (m, 2H), 1.80 (ddd, J=14.3, 8.9, 5.9 Hz, 2H), 1.66 (s, 3H)

7525-64-6 4-Methyltetrahydro-2H-pyran-4-ol 12347118, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P.V.K. Suresh; Scola, Paul Michael; (403 pag.)US9527885; (2016); B2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4677-20-7,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.

Into a 50-mL 3-necked round-bottom flask, was placed tert-butyl N-[2-[([3-[4-(3- hydroxycyclobutoxy)phenyl] -1 -(oxan-2-yl)- 1 H-pyrazol-4-yl]methyl)(methyl)amino] ethyl] – N-methylcarbamate (500 mg, 0.97 mmol, 1.00 equiv),N,N-dimethylformamide (10 mL). The temperature was cooled to 0C. To this was added sodium hydride (120 mg, 5.00 mmol, 5.15 equiv, 60% in mineral oil) in batches. The mixture was stirred for 1 h at R.T. Then to the mixture was added 4-(2-bromoethyl)oxane (470 mg, 2.43 mmol, 2.51 equiv). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 30 mL of water. The resulting solution was extracted with 3×3 0 mL of ethyl acetate. The resulting mixture was washed with 3×30 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (0%-60%). The collected fractions were combined and concentrated under vacuum. This resulted in 450 mg (74%) of tert-butyl N-methyl-N-[2- [methyl([ [1 -(oxan-2-yl)-3 -(4- [3 -[2-(oxan-4-yl)ethoxy] cyclobutoxy]phenyl)1H-pyrazol-4-yl]methyl])amino]ethyl]carbamate as yellow oil. LCMS (Method A, ESI): RT = 1.37mm, m/z =627.4 [M+H].

The synthetic route of 4677-20-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; EPIZYME, INC.; MITCHELL, Lorna, Helen; SWINGER, Kerren, Kalai; SHAPIRO, Gideon; BORIACK-SJODIN, Paula, Ann; (104 pag.)WO2016/44556; (2016); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

2081-44-9, Tetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: Synthesis of Toluene-4-sulfonic acid tetrahydro-pyran-4-yl ester To a solution of 133 g (1.31 mol) of tetrahydro-pyran-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 room temperature and stirred for 18 h. The reaction is poured onto a stirred mixture of aqueous HCl/ice. The resulting precipitate is isolated by filtration and dissolved in DCM (1 L). The organic layer is washed with 1M aqueous HC1 solution (1 L), followed by saturated aqueous NaHC03 solution (1 L) and is then dried over Na2S04.Filtration and concentration of the filtrate under reduced pressure gives 300 g of toluene-4- sulfonic acid tetrahydro-pyran-4-yl ester as an orange oil. Yield: 90%, ES-MS: m/z: 257[M+H], 279 [M+Na]. 1H-NMR (250 MHz, CHLOROFORM-d) delta ppm 1.66 – 1.96 (4 H, m), 2.45 (3 H, s), 3.47 (2 H, ddd, 7=11.76, 8.19, 3.50 Hz), 3.79 – 3.95 (2 H, m), 4.69 (1 H, tt, 7=8.13, 4.13 Hz), 7.35 (2 H, d, 7=8.07 Hz), 7.76 – 7.87 (2 H, m)

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; BARTOLOZZI, Alessandra; BERRY, Angela; RIETHER, Doris; ERMANN, Monika; JENKINS, James Edward; MUSHI, Innocent; WO2011/88015; (2011); 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.

Prepared as described by adaptation of the following literature reference: Radziszewski, J. G. et al. J. Am. Chem. Soc. 1993, 115, 8401. To 97 g (810 mmol) of (tetrahydro-pyran-4-yl)-methanol in 2-methyltetrahydrofuran (190 mL) are added 165 mL of 50% aq. NaOH solution. To this stirred suspension is added dropwise with cooling a solution of p-toluene-sulfonylchloride (283 g, 1.46 mol) in 2-methyltetrahydrofuran (280 mL). The reaction is stirred at 30-35 C. for 18 h. The suspension is poured into a mixture of ice-water (280 mL) and aq. HCl solution (37%, 203 mL). After addition of methylcyclohexane (1.4 L) and further ice-water (0.2 L), the reaction mixture is stirred for 2 h in an ice-bath. The resulting crystalline precipitate is isolated by filtration and washed with methylcyclohexane (0.5 L) and water (0.5 L). Drying under reduced pressure at 40 C. gave 216 g of toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester. Yield: 99%; ESI-MS: 271 [M+H]+, 14774-37-9

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

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

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

Step 1: To a solution of (3-methoxy-5-methylpyrazin-2-yl)methanamine (150 mg, 979.2 mol), tetrahydro-2H-pyran-3-carboxylic acid (127.4 mg, 979.2 mol) in DCM (10 mL) was added HATU (670.2 mg, 1.8 mmol) and triethylamine (198.2 mg, 1.9 mmol). The mixture was stirred at 25¡ãC for 16 hours. The mixture was diluted with water (15 mL), extracted with DCM (3 x 30 mL). The combined organic layer was washed with brine (30 mL), dried overNa2504, filtered and concentrated. The residue was purified by preparative TLC (EAIMeO H =20/1) to give N-((3-methoxy-5-methylpyrazin-2-yl)methyl)tetrahyd ro-2H-pyran-3- carboxamide (130 mg, 50percent yield)., 873397-34-3

The synthetic route of 873397-34-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2016/174188; (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.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.

5- (4-Fluorophenyl) -4-oxo-1,4-dihydropyridazine-3-carboxylic acid ethyl ester (500.0 mg, 1.9 mmol, 1.0 eq) was dissolved in DMF (5 mL) and added Cesium carbonate (1.85 g, 5.70 mmol, 3.0 eq) and 4-bromotetrahydro-2H-pyran (628.7 mg, 3.81 mmol, 2.0 eq) were stirred at 120 C for 5 hours. The reaction was monitored by TLC, and the reaction was concentrated under reduced pressure. Ethyl acetate (15 mL) and water (20 mL) were added, and the layers were separated. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate). Esters = 8: 1 to 2: 1) to obtain the product (342.0 mg, yield: 51.9%).

25637-16-5, The synthetic route of 25637-16-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Li Lin; Wan Zhonghui; (107 pag.)CN110041316; (2019); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

344329-76-6, Tetrahydro-2H-pyran-4-carboxamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Thionyl chloride (10.0 mL, 137 mmol) was added to oxane-4-carboxamide (3.0 g, 23 mmol) and thereaction mixture was refluxed for 4 h, after which the reaction mixture was poured over ice andbasified to pH 14 with NaOH (50%). The aqueous solution was extracted with EtOAc (3 ¡Á 50 mL),dried (Na2SO4) and concentrated in vacuo to give the product as a pale yellow oil (2.4 g, 94%). Theproduct obtained did not require any further purification.IR numax 2961, 2932, 2851, 2240, 1468, 1446, 1390, 1242, 1125, 1066, 1011 cm-1;1H-NMR (CDCl3, 500 MHz): 3.91 (2H, ddd, J 11.9, 6.3, 3.6, 2¡Á2-HA), 3.61 (2H, ddd, J 11.9, 7.8, 3.3,2¡Á2-HB), 2.91-2.85 (1H, m, 4-H), 1.99-1.92 (2H, m, 2¡Á3-HA), 1.91-1.84 (2H, m, 2¡Á3-HB);13C-NMR (CDCl3, 75 MHz): 121.2, 65.6, 28.9, 25.3;HRMS (ESI+): Calculated for C6H10NO ([M+H]+): 112.0756. Found: 112.0754, Delta -1.8 ppm., 344329-76-6

The synthetic route of 344329-76-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Craven, Philip; Aimon, Anthony; Dow, Mark; Fleury-Bregeot, Nicolas; Guilleux, Rachel; Morgentin, Remy; Roche, Didier; Kalliokoski, Tuomo; Foster, Richard; Marsden, Stephen P.; Nelson, Adam; Bioorganic and Medicinal Chemistry; vol. 23; 11; (2015); p. 2629 – 2635;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

720706-20-7, (4-Amino-4-tetrahydropyranyl)methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,720706-20-7

The 2-hydroxyethylamine was reacted with isobutyraldehyde according to Method B4c, Step 1 to afford 2-isopropyl-1-aza-3,8-dioxaspiro[4.5]decane

The synthetic route of 720706-20-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bayer Corporation; US6353006; (2002); B1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics