Tag: M.W:200-300

101691-94-5, 4-(Iodomethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2 g (10.3 mmol) 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 2.9 mL (20.6 mmol) 4-(iodomethyl)-tetrahydro-2H-pyran are dissolved in 200 mL DMF and 4.274 g (30.9 mmol) K2CO3 are added. The mixture is shaken at 80 C. for 5 h. After cooling to r.t. the mixture is filtered, the filtrate is concentrated in vacuo to approximately 60 mL. The product is separated using HPLC-MS (Gilson, mass flow 120 mL/min, 10 mum, 200 g Sunfire RP18, ACN/water/TFA). The product fractions are combined and freeze-dried to yield 115 mg product (3.8%) R7.6., 101691-94-5

As the paragraph descriping shows that 101691-94-5 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; BINDER, Florian; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; VINTONYAK, Viktor; US2014/275025; (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.1408168-76-2,Potassium trifluoro(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)borate,as a common compound, the synthetic route is as follows.

To a stirred solution of 2,3-dibromo-6-methoxypyridine, Step 1 : Example 31 , (1.4 g, 5.30 mmol), potassium trifluoro(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)borate, Step 3: Example 31 , (3.7 g, 15.90 mmol) and cataCXiumA (0.35 g, 1.06 mmol) in dry 1 ,4 dioxane (12 mL), was added a solution of cesium carbonate (1.62 g, 31.80 mmol) in water (4 mL) at RT. The reaction mixture was degassed for 10 min using N2 gas. Then Pd(OAc)2 (0.33 g, 1.59 mmol) was added at RT and the reaction mixture was heated to 100 ? for 20 h. Completion of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with EtOAc (10mL) and brine (10mL) and the aqueous layer was extracted with EtOAc (2 x 20 mL), washed with water (10 mL), brine (10 ml_), dried over Na2SC>4 and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography using 12-15% EtOAc in petroleum ether to afford the tittle compound. Yield: 57% (1.1 g, brown gummy solid). 1H NMR (400 MHz, CDCI3): d 7.40 (d, J = 8.4 Hz, 1 H), 6.53 (d, J = 8.0 Hz, 1 H), 4.62 (d, J = 20.8 Hz, 2H), 4.20-4.11 (m, 1 H), 3.95-3.89 (m, 2H), 3.88 (s, 3H), 3.81 – 3.70 (m, 2H), 3.61-3.51 (m, 1 H), 3.50-3.46 (m, 2H), 3.07 (t, J = 7.2 Hz, 2H), 2.91 (t, J = 7.2 Hz, 2H), 1.81 (t, J = 8.4 Hz, 2H), 1.71 (t, J = 10.0 Hz, 2H), 1.62-1 .59 (m, 8H). LCMS: (Method A) 366.2 (M+H), 1.7 min, 90.1 % (Max)., 1408168-76-2

1408168-76-2 Potassium trifluoro(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)borate 74787645, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; WISHART, Grant; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; RAKESH, Paul; (250 pag.)WO2020/39028; (2020); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

33821-94-2, 2-(3-Bromopropoxy)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Scheme 16. Preparation of rifabutin bisphosphonate conjugates 89.; [00282] Tetraethyl 4-(2-Tetrahydro-2H-pyranyloxy)butylene-1,1-bisphosphonate (80): To a suspension of NaH (60% suspension in mineral oil, 900 mg, 22.0 mmol) in dry THF (20 ml.) was added dropwise tetraethyl methylenebisphosphonate (6.46 g, 22.4 mmol). The resulting clear solution was stirred 15 min at room temperature, after which 2-(3- bromopropoxy)tetrahydro-2H-pyran (5.05 g, 22.6 mmol) was added dropwise. The reaction mixture was heated to reflux for 6 h, diluted with CH2CI2 (75 ml.) and washed with brine (2 x 50 ml_), dried (MgSO4) and evaporated. It was used as such in the following step.

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

Reference£º
Patent; DIETRICH, Evelyne; REDDY, Ranga; TANAKA, Kelly; KANG, Ting; LAFONTAINE, Yanick; RAFAI FAR, Adel; TARGANTA THERAPEUTICS CORP.; WO2010/19511; (2010); 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.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

Step 2: 4-(2-chloro-8-iodo-9-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-9H-purin- 6-yl)morpholineTo a suspension of 4-(2-chloro-8-iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6- yl)morpholine (0.655 g, 1.46 mmol) in methanol (6 mL) was added a catalytic amount of p- toluenesulfonic acid (25 mg, 0.14 mmol). The reaction mixture was heated at 50 C for an overnight period. After this time, the mixture was cooled to room temperature and the volume of methanol was reduced by vacuum evaporation. The resulting residue was diluted with sat.aqueous NaHC03 solution. The precipitate that formed was collected by filtration. In total, 295 mg (56%) of 4-(2-chloro-8-iodo-9H-purin-6-yl)morpholine was obtained as a white solid which was dissolved in anhydrous DMF (2.5 mL). Cesium carbonate (0.53 g, 1.61 mmol) was added and the mixture was stirred together 10 min at 23 C. Subsequently l-(2H-3,4,5,6- tetrahydropyran-2-yloxy)-3-bromopropane (0.54 g, 2.42 mmol) was introduced to the mixture. The resulting reaction mixture was heated at 50 C for 2 h. Complete conversion was observed at the end of this period. The reaction was worked up by dilution with 1 N HCl and EtOAc. The phases were separated and the aqueous layer was extracted twice with EtOAc. The combined organic portions were dried over MgS04, filtered and concentrated in vacuo. The residue was purified by FCC (40 g silica gel column, 0-50% EtOAc in heptane) to give 385 mg (94% yield) of 4-(2-chloro-8-iodo-9-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-9H-purin-6-yl)morpholine as a pale yellow solid. MS (ESI+): m/z 508.0 (M+H+), 33821-94-2

The synthetic route of 33821-94-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA-ROCHE AG; DOTSON, Jennafer; HEALD, Robert Andrew; HEFFRON, Timothy; JONES, Graham Elgin; KRINTEL, Sussie Lerche; MCLEAN, Neville James; NDUBAKU, Chudi; OLIVERO, Alan G.; SALPHATI, Laurent; WANG, Lan; WEI, BinQing; WO2012/82997; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

101691-65-0, (Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3: Synthesis of Thioacetic acid S-(tetrahydro-pyran-4-ylmethyl) ester Prepared as described by adaptation of the following literature reference:Watson, R.J. et al. Tetrahedron Lett. 2002, 43, 683-685. To a solution of 224 g (0.83 mol) of toluene-4- sulfonic acid tetrahydro-pyran-4-ylmethyl ester in methyl isobutylketone (1.6 L) are added 189 g (1.66 mol) of potassium thioacetate. The beige suspension is stirred at 70 C for 4.5 h. The reaction mixture is cooled to room temperature and water (1.8 L) is added. The organic layer is washed with 10% aqueous K2CO3 solution (1.8 L) and water (1 L). The organic layer is filtered through celite (20 g), activated charcoal (20 g) and Na2S04 (20 g) and the filtrate is concentrated under reduced pressure. The residual oil is azeotroped with methylcyclohexane (200 mL) and n-heptanes (250 mL) to afford 138 g of thioacetic acid S-(tetrahydro-pyran-4-ylmethyl) ester as a yellow-orange oil (CAUTION: Stench.). Yield: 96%; ES-MS: m/z 175 [M+H]; 1H NMR (400 MHz,CHLOROFORM-d) delta ppm 1.23 – 1.40 (2 H, m), 1.59 – 1.78 (3 H, m), 2.33 (3 H, d, 7=4.16 Hz), 2.82 (2 H, dd, 7=6.24, 3.79 Hz), 3.27- 3.39 (2 H, m), 3.88 – 4.02 (2 H, m)

101691-65-0, As the paragraph descriping shows that 101691-65-0 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

53911-68-5, 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

53911-68-5, The solution of 3-(4-chlorophenyl)glutaric anhydride (449 mg) and anthranilamide (272 mg) in toluene (8 ml) was heated to reflux for 4 h. After removal of the solvent the residue was dried in vacuo. The off- white solid was dissolved in 2M sodium hydroxide (3 ml) and stirred under reflux for 2 h. After cooling to room temperature acetic acid (0.5 ml) was added with stirring. The precipitate formed was isolated by suction filtration, washed, and dried in vacuo to give 3-(4-chlorophenyl)-4-(4-hydroxy-2-quinazolinyl)butanoic acid (0.57 g) as colourless solid.1H-NMR (500 MHz, DMSO-d6)): delta (ppm)=2.62 (dd, J=16.0, 9.3 Hz, 1H), 2.74 (dd, J=16.0, 5.6 Hz, 1H), 2.86 (dd, J=14.4, 7.7 Hz, 1H), 2.93 (dd, J=14.4, 7.8 Hz, 1H), 3.74 (m, 1H), 7.32 (m, 4H), 7.44 (dt, J=8.0, 1.1 Hz, 1H), 7.59 (d, J=8.0, 1H), 7.76 (dt, J=7.7, 1.6 Hz, 1H), 8.04 (dd, J=7.9, 1.2 Hz, 1H), 12.10 (s, br, 1H), 12.20 (s, br, 1H).13C-NMR and DEPT (125 MHz, DMSO-d6): delta (ppm)=38.82 (CH), 39.37 (CH2), 40.75 (CH), 120.70 (C), 125.56 (CH), 125.98 (CH), 126.75 (CH), 128.07 (CH), 129.33 (CH), 130.90 (C), 134.19 (C), 142.22 (C), 148.59 (C), 155.17 (C), 161.59 (CO), 172.55 (CO).

The synthetic route of 53911-68-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1408168-76-2, Potassium trifluoro(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)borate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A schlenk flask was charged with the compound obtained in example 1 (0.56 g, 1.3 mmol), bis(di-fe/f-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(ll) (94 mg, 0.13 mmol), potassium trifluoro(2-((tetrahydro-2/-/-pyran-2-yl)oxy)ethyl)borate (0.34 g, 1.6 mmol), and CS2CO3 (1.7 g, 5.3 mmol) and it was evacuated and backfilled with argon. Tolueneil-hO (4:1 , 10 mL) was added and the reaction mixture was heated at 100 C overnight. H2O was added and the product was extracted with EtOAc. The combined organic layers were dried over Na2S04, filtered and concentrated to dryness to give the title compound (0.62 g, Yield: 99%)., 1408168-76-2

1408168-76-2 Potassium trifluoro(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)borate 74787645, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ESTEVE PHARMACEUTICALS, S.A.; FERNANDEZ-DONIS, Ariadna; DIAZ-FERNANDEZ, Jose, Luis; ALMANSA-ROSALES, Carmen; LORENTE-CRIVILLE, Adriana; (0 pag.)WO2020/89400; (2020); 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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

To carbazole (111 mg, 0.66 mmol) was added 4-(iodomethyl)tetrahydro-2H- pyran (150 mg, 0.66 mmol), sodium hydride (60% in mineral oil, 27 mg, 0.8 mmol), and dimethylsulfoxide. After 9 days, the mixture was placed on silica and purified by flash chromatography (15 % ethyl acetate, 85 % hexanes) to yield the title compound (24 mg, 14 %)., 101691-94-5

The synthetic route of 101691-94-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; IMMUSOL INCORPORATED; WO2008/21745; (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.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

53911-68-5, 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Commercial 4-bromo-1,2-phenylenediamine (561 mg) and 3-(4-chlorophenyl)-glutaric anhydride (674 mg) were dissolved in THF (1 ml) with heating. The dark solution was stirred at rt for 1 h. Then the solution was decolourised with activated carbon and filtered. The filtrate was concentrated and the solid residue dried in vacuo. The solid was dissolved in a mixture of acetic acid (4 ml) and conc. HCl (2 ml) and stirred under reflux for 3 h. All volatiles were removed at the water aspirator and the residue was recrystallised from ethanol /EtOAc 1:3 to give a crude (0.47 g). The impure crude was again refluxed with acetic acid /conc. HCl 2:1 for 1 h to leave after concentration and acetone trituration 4-(5-bromo-2-benzimidazolyl)-3-(4-chlorophenyl)butanoic acid?HCl (0.3 g) as light greyish solid.1H-NMR (500 MHz, DMSO-d6): delta (ppm)=2.72 (dd, J=16.2, 8.6 Hz, 1H), 2.83 (dd, J=16.3, 8.2 Hz, 1H), 3.43 (dd, J=14.9, 9.2 Hz, 1H), 3.55 (dd, J=14.9, 6.9 Hz, 1H), 3.85 (m, 1H), 7.30 (d, J=8.5 Hz, 2H), 7.35 (d, J=8.5 Hz, 1H), 7.60 (dd, J=8.7, 1.7 Hz, 1H), 7.67 (d, J=8.7 Hz, 1H), 7.94 (d, J=1.7 Hz, 1H).13C-NMR and DEPT (125 MHz, DMSO-d6): delta (ppm)=32.66 (CH2), 39.19 (CH), 39.60 (CH2), 115.57 (CH), 116.42 (CH), 117.34 (C), 128.14 (CH), 128.34 (2CH), 129.14 (2CH), 130.26 (C), 131.44 (C), 132.32 (C), 140.69 (C), 153.07 (C), 172.12 (CO).MS (+ESI): m/z=393 (M+H)., 53911-68-5

As the paragraph descriping shows that 53911-68-5 is playing an increasingly important role.

Reference£º
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics