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

Reference Example 16 ethyl 2-(4-bromo-5-methoxy-1H-indazol-1-yl)-3-(tetrahydro-2H-pyran-4H-yl)propanoate [Show Image] To a solution of diisopropylamine (1.35 g) in a mixed solvent of tetrahydrofuran (30 mL) and 1,3-dimethyl-3,4,5,6-tetrahydropyrimidin-2(1H)-one (15 mL) was slowly added 1.6M hexane solution (16.1 mL) of n-butyllithium at -70C under a nitrogen atmosphere. The reaction mixture was stirred at -70C for 15 min, and a solution of ethyl (4-bromo-5-methoxy-1H-indazol-1-yl)acetate (3.65 g) in tetrahydrofuran (5 mL) was slowly added thereto. The reaction mixture was stirred at – 70C for 20 min, 4-(iodomethyl)tetrahydro-2H-pyran (2.80 g) was added thereto, and the mixture was stirred overnight at room temperature. To the reaction mixture was added 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (1.36 g, yield 28%) as pale-yellow crystals from the fraction eluted with ethyl acetate-hexane (2:3, volume ratio). melting point 76-77C. MS:413(MH+)., 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; Takeda Pharmaceutical Company Limited; EP2266983; (2010); 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,33821-94-2

Tetraethyl 4-(2-Tetrahydro-2H-pyranyloxy)butylene-1,1-bisphosphonate (31): 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 CH2Cl2 (75 mL) and washed with brine (2*50 mL), dried (MgSO4) and evaporated. It was used as such in the following step.

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

Reference£º
Patent; TARGANTA THERAPEUTICS, INC.; US2011/263534; (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.53911-68-5,4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.,53911-68-5

Prepared by dissolving an equimolar mixture of 3-(4-chlorophenyl)glutaric anhydride and commercial 5-chloro-2-hydroxyaniline in boiling dichloromethane. Upon cooling to rt product precipitates and yields after isolation 87% of N-(2-hydroxy-5-chlorophenyl)-3-(4-chlorophenyl)glutaramic acid as colourless crystals

53911-68-5 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione 104639, aTetrahydropyrans compound, is more and more widely used in various fields.

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

1240390-36-6, tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1. Into a 25 mL round flask containing a solution of tert-butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate (100 mg, 0.5 mmol) in dichloromethane (5 mL) were added triethyl amine (0.15 mL, 0.9 mmol) and benzyl chloroformate (0.1 mL, 0.7 mmol) and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with dichoromethane and washed with saturated sodium bicarbonate, water, and brine solution sucessively. The organic fraction was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude produt was purified by flash chromatography eluting with ethyl acetate in petroleum ether (20-25%) to get benzyl tert-butyl ((3R,4R)- tetrahydro-2H-pyran-3,4-diyl)dicarbamate as a liquid. NMR (CDCl3, 400 MHz): delta 7.37-7.35 (m, 5H), 5.45 (brs, 1H), 5.12 (s, 2H), 3.94-3.81 (m, 4H), 3.59-3.53 (m, 1H), 2.01-1.96 (m, 2H), 1.45 (s, 9H). MS calc’d [M-Boc+H]+ 251.2, found 251.2., 1240390-36-6

As the paragraph descriping shows that 1240390-36-6 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; LIM, Jongwon; ALTMAN, Michael, D.; CHILDERS, Matthew, L.; GIBEAU, Craig, R.; HO, Ginny Dai; TSUI, Honchung; (80 pag.)WO2016/144844; (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.101691-65-0,(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

The quantity of reagents and materials used in the following procedure were based on the quantity of N-(l-Methyl-l-phenylethyl)-lH-indazole-3-carboxamide obtained in the preceding step, as indicated. A solution of N-(l -methyl- l-phenylethyl)-lH-indazole-3-carboxamide (1.0 molar eq.) in anhydrous DMF (5 volumes) was mixed with anhydrous potassium carbonate (5.84 molar eq.). (Tetrahydro-2H-pyran-4-yl) methyl 4-methylbenzenesulfonate (1 molar eq.) was added portion wise over a period of 5 minutes at ambient temperature to the reaction mixture. The resulting reaction mixture was heated to 70C for at least 15 hours using an oil bath. The reaction mixture was evaporated at a 40C bath temperature under reduced pressure to remove the DMF. The evaporated residue was mixed with ethyl acetate (5 volumes) and then poured into ice (5 weight equivalents). The mixture was stirred until the ice melted. The bilayer was separated and the aqueous layer extracted with ethyl acetate (4 x 3 volumes). The combined extracts were washed with 50% saturated sodium carbonate solution (4 x 1 volume), then dried over sodium sulfate and filtered. The filtrate was evaporated at a 40 bath temperature and co-evaporated with ethyl acetate (3 x 2.5 volumes). The resultant residue was redissolved and hot ethyl acetate (4 volumes) and filtered through 60 angstrom silica (2.5 volumes) topped with a layer of anhydrous sodium sulphate. The filter bed was washed with hot ethyl acetate (2 volumes per fraction) until all of the product was released. Product containing fractions were evaporated with a bath temperature of 40C. The crude product was triturated with methyl tert-butyl ether (MTBE)(2 volumes) at room temperature of the 2 hours, and then in an ice bath for one hour. The suspension was filtered, then rinsed with cold MTBE (4 x 1 volume). The resulting white solid was then dried under vacuum to constant weight, mp 112.7 ¡À 0.5 . IR vmax/cm_1 3328, 1664 (amide). lU NMR (400 MHz, DMSO-d6) delta 8.03 (1H, d, HI), 7.97 (1H, s, H5), 7.82 (1H, d, H4), 7.41-7.44 (3H, m, H2, H3), 7.33 (2H, dt, H8), 7.20 (2H, dd, H7), 4.41 (2H, d, H10), 3.84 (2H, d, H13), 3.25 (2H, m, H14), 2.23 (1H, m, H15), 1.74 (6H , s, H6), and 1.39 (4H, m, Hl l, H12). MS (ESI+) m/z 378 (MH+). Anal. Calcd for C23H27N3O2: C, 73.18; H, 7.21; N, 11.13. Found: C, 73.44; H, 7.22; N, 11.23. 1 13 H and i3C NMR scans for SGT-42 are provided in Figures 1 and 2, respectivley., 101691-65-0

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

Reference£º
Patent; BOWDEN, Matthew James; WILLIAMSON, James Peter Bernard; WO2014/167530; (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 degassed solution of intermediate (10e) (1.35 g, 2.60 mmol) in toluene (15 ml_) and water (5 ml_) were added potassium 2-(tetrahydro-2/-/-pyran-2-yloxy)ethyltrifluoroborate (613 mg, 2.60 mmol), cesium carbonate (2.54 g, 7.79 mmol), RuPhos (121 mg, 0.26 mmol) and palladium(ll) acetate (29 mg, 0.13 mmol). The flask was sealed and the mixture was heated at 95C for 5h. The mixture was cooled to rt and water was added. The layers were separated. The aqueous layer was extracted with toluene. The combined organic layers were washed with brine, dried over Na2S04 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ AcOEt 10/0 to 5/5) to provide intermediate (1 1 a) (1 .21 g, 2.12 mmol, 81%) as a yellow oil. MS m/z ([M+Na]+) 591., 1408168-76-2

The synthetic route of 1408168-76-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MUTABILIS; BARBION, Julien; CARAVANO, Audrey; CHASSET, Sophie; CHEVREUIL, Francis; LE STRAT, Frederic; SIMON, Christophe; BRIAS, Julie; LEBEL, Remi; (80 pag.)WO2020/25543; (2020); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1152567-60-6, 4-(4-Bromophenyl)tetrahydro-2H-pyran-4-carboxylic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of 4-[4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]-tetrahydro- pyran-4-carboxylic acid To a mixture of 1-20 (91 mg, 0.32 mmol), R-8 (95 mg, 0.38 mmol),bis(triphenylphosphine)palladium(II)dichloride (27 mg, 0.03 mmol) in THF (2.0 mL) at room temperature is added KC03 (128 mg, 1.3 mmol), and H20 (0.3 mL). The mixture is heated in the microwave at 120 C for 30 minutes, allowed to cool to roomtemperature, and concentrated in vacuo. The residue is purified by flash chromatography (Si02, 0-10% MeOH in CH2C12) to give the title intermediate 1-32 (83 mg).

1152567-60-6, The synthetic route of 1152567-60-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela; CHEN, Zhidong; DE LOMBAERT, Stephane; EMMANUEL, Michel Jose; LOKE, Pui Leng; MAN, Chuk Chui; MORWICK, Tina Marie; TAKAHASHI, Hidenori; WO2012/82817; (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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

Synthesis of 3-Methoxy-4-(tetrahydro-pyran-4-ylmethoxy)-benzonitrile (For Example1 .0 g 4-Hydroxy-3-methoxybenzonitrile, 1.1 g potassium carbonate and 2.0 g 4-(iodomethyl)- tetrahydropyran were placed in 20 mL acetone and heated to reflux overnight. After this time,1 .1 g potassium carbonate was added and the reaction was heated at reflux for a further 2 h before more 0.93 g potassium carbonate was introduced and reflux was continued for a further 3 h. The mixture was then cooled to ambient temperature and concentrated under reduced pressure. The material that remained was partitioned between diethyl ether and water and the aqueous phase was removed and extracted with additional diethyl ether. The combined organic fractions were dried, filtered and the filtrate was concentrated under reduced pressure. Purification by silica gel chromatography (Si02: ethyl acetate/heptanes: 10% to 30%) provided the title compound. Yield: 307 mg (19% of theory)Analysis: HPLC-MS (Method B): Rt: 1 .85 min., 101691-94-5

101691-94-5 4-(Iodomethyl)tetrahydro-2H-pyran 2795507, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; DAHMANN, Georg; FIEGEN, Dennis; HANDSCHUH, Sandra; KLICIC, Jasna; LINZ, Guenter; SCHAENZLE, Gerhard; SCHNAPP, Andreas; EAST, Stephen P.; MAZANETZ, Michael Philip; SCOTT, John; WALKER, Edward; WO2011/92128; (2011); 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,101691-65-0

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 Na2SO4 (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 (2H, m), 1.59-1.78 (3H, m), 2.33 (3H, d, J=4.16 Hz), 2.82 (2H, dd, J=6.24, 3.79 Hz), 3.27-3.39 (2H, m), 3.88-4.02 (2H, m)

The synthetic route of 101691-65-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Boehringer Ingelheim International GmbH; US2010/76029; (2010); 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.53911-68-5,4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.,53911-68-5

The solution of commercial 3,4-diaminobenzophenone (0.43 g) and 3-(4- chlorophenyl)glutaric anhydride (0.45 g) in 1,4-dioxane (3 ml) was stirred under reflux for 0.5 h. 4M HCI in 1,4-dioxane (3 ml) was added and the solution is further heated to reflux for 2.5 h. After cooling to rt the precipitate is collected by suction filtration and washed with 1,4-dioxane and diethyl ether. The crude is recrystallised from acetic acid to give 4-(5-benzoyl-2-benzimidazolyl)-3-(4-chlorophenyl)butanoic acid HCI (0.64 g) as light brown solid.1H-NMR (500 MHz, DMSOd5)): delta (ppm) = 2.74 (dd, J = 16.2, 8.6 Hz, IH), 2.85 (dd, J = 16.2, 6.1 Hz, IH), 3.50 (dd, J = 15.0, 9.1 Hz, IH), 3.60 (dd, J = 15.0, 6.9 Hz, IH), 3.91 (m, IH), 7.32 (d, J = 8.5 Hz, 2H), 7.39 (d, J = 8.5 Hz, 2H), 7.58 (t, J = 7.6 Hz, 2H), 7.70 (t, J = 7.4 Hz, IH), 7.75 (dd, J = 8.3, 1.3 Hz, 2H), 7.83 (dd, J = 8.6, 1.5 Hz, IH), 7.86 (d, J = 8.6 Hz, IH), 8.01 (d, J = 1.4 Hz, IH). 13C-NMR and DEPT (125 MHz, DMSOd6) : delta (ppm) = 32.83 (CH2), 39.17 (CH), 39.67 (CH2), 113.91 (CH), 115.78 (CH), 126.51 (CH), 128.37 (2 CH), 128.52 (2 CH), 129.19 (2 CH), 129.54 (2 CH), 131.02 (C), 131.46 (C), 132.70 (CH), 133.79 (C), 133.95 (C), 136.90 (C), 140.75 (C), 154.47 (C), 172.14 (CO), 194.71 (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; ENGEL, Matthias; FROeHNER, Wolfgang; STROBA, Adriane; BIONDI, Ricardo M.; WO2010/43711; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics