Day: November 10, 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.116131-44-3,3-(Bromomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

Intermediate 14: /V2-Butyl-8-methoxy-9-(tetrahvdro-2H-pyran-3-ylmethyl)-9/-/-purine- 2,6-diamine To a solution of /V2-butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid salt (100 mg) in dry N,N-dimethylformamide (1 ml) at room temperature and under nitrogen was added potassium carbonate (158 mg) in one go. The reaction was stirred at 60C for 1.5 hours and then cooled to 50C. A solution of 3- (bromomethyl)tetrahydro-2H-pyran (56 mg) in dry N,N-dimethylformamide (0.3 ml) was added in one go and the reaction heated at 500C for 16 hours. The reaction was diluted with ethyl acetate (15 ml) and washed with water (5 ml). The organic layer was separated, dried over magnesium sulphate, filtered, and concentrated in vacuo. The product was purified by Ci8 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluant (20-60%) to afford the title compound as a yellow oil (45mg). MS calcd for (Ci6H26N6O2)+ = 334 MS found (electrospray): (M+H)+ = 335.

116131-44-3, As the paragraph descriping shows that 116131-44-3 is playing an increasingly important role.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/101867; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125552-89-8, 4-(Bromomethyl)tetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 3,5-dichloro-4-((l,4-dimethyl-6-(trifluoromethyl)-lH-indol-2-yl)methyl)pyridin-2-ol (200 mg, 0.514 mmol) in DMF (2.6 ml) was added potassium carbonate (284 mg, 2.056 mmol) and 4- (bromomethyl)tetrahydropyran (0.135 ml, 1.028 mmol) and reaction mixture was stirred at 100C for 2 hours. The reaction mixture was diluted with water and the obtained aqueous layer was extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with 5-100% ethyl acetate in dichloromethane) then by preparative LCMS to give 2-((3,5- dicMoro-2-((tetrahydro-2H-pyran-4-yl)methoxy)pyridin-4-yl)methyl)-l,4-dimethyl-6- (trifluoromethyl)-lH-indole (108 mg, 40%) as a white solid LC/MS (Method g) Rt = 2.26 min.; MS m/z: 487 [M+H]+ NMR (DMSO-d6, 400MHz): delta 8.32 (m, 1H), 7.70 (s, 1H), 7.07 (s, 1H), 5.80 (s, 1H), 4.42 (s, 2H), 4.24 (d, J=6.3 Hz, 2H), 3.91 (s, 3H), 3.88 (m, 2H), 3.34 (m, 2H), 2.38 (s, 3H), 2.07 (m, 1H), 1.68 (m, 2H), 1.39 (m, 2H) and 3,5-dichloro-4-((l,4-dimethyl-6-(trifluoromethyl)-lH-indol-2-yl)methyl)-l- ((tetrahydro-2H-pyran-4-yl)methyl)pyridin-2(lH)-one (46 mg, 18%) as a white solid. LC/MS (Method g) R, = 1.84 min.; MS m/z: 487 [M+H]+ NMR (DMSO-d6, 400MHz): delta 8.14 (s, 1H), 7.69 (s, 1H), 7.07 (s, 1H), 6.00 (s, 1H), 4.30 (s, 2H), 3.82-3.95 (m, 7H), 3.20-3.30 (m, 2H), 2.41 (s, 3H), 2.09 (m, 1H), 1.48 (m, 2H), 1.30 (m, 2H).

125552-89-8, 125552-89-8 4-(Bromomethyl)tetrahydropyran 2773286, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; ABBVIE INC.; ARGIRIADI, Maria A.; BREINLINGER, Eric; CUSACK, Kevin P.; HOBSON, Adrian, D.; POTIN, Dominique; BARTH, Martine; AMAUDRUT, Jerome; POUPARDIN, Olivia; MOUNIER, Laurent; KORT, Michael, E.; (392 pag.)WO2016/198908; (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.108-55-4,Dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

Intermediate 1: 5-(Benzyloxy)-5-oxopentanoic AcidDissolve glutaric anhydride (8.76¡Á10-2 mol) in dichloromethane (300 ml) and place under stirring. Add 4-dimethylaminopyridine (7.88¡Á10-2 mol) and benzyl alcohol (7.88¡Á10-2 mol) and then leave the reaction mixture at ambient temperature. After 4 hours and 30 minutes, the mixture is hydrolysed with aqueous 5% sodium carbonate solution (200 ml). Separate the two phases by decanting. The aqueous phase is then acidified with aqueous 1M hydrochloric acid solution and subsequently extracted with ethyl acetate. The organic phase is washed with brine, dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure.The title product is obtained in the form of a white solid which is used without subsequent purification., 108-55-4

108-55-4 Dihydro-2H-pyran-2,6(3H)-dione 7940, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; LES LABORATOIRES SERVIER; US2010/286225; (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.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

To a solution of 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy)-4-(4- (2-phenylpyrrolidin-1-yl) piperidin-1-yl) benzoic acid (145 mg, 0.3 mmol) in dichloromethane (25 mL) were added o- (7-azabenzotriazol-1-yl) -N, N, N’, N’-tetramethyluronium hexafluorophosphate (171 mg, 0.45 mmol), triethylamine (1 mL) and 4-dimethylaminopyridine (36 mg, 0.3 mmol). The mixture was stirred for 0.5 h at r.t. Then 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzenesulfonamide (189 mg, 0.6 mmol) was added. The reaction was continually stirred overnight at r.t. Afterwards, the mixture was washed with water (10 mL) and the organic layers were dried over anhydrous Na 2SO 4 and concentrated. The residue was further purified by prep-HPLC to give the desired product (50 mg, 21.5 %). 1H NMR (400 MHz, DMSO-d 6) delta ppm: 11.68 (m, 2H), 8.58 (d, J = 5.6 Hz, 1H), 8.54 (d, J = 2.4 Hz, 1H), 8.02 (d, J = 2.4 Hz, 1H), 7.77 (d, J = 9.2 Hz, 1H), 7.60-7.40 (m, 5H), 7.33-7.25 (m, 3H), 7.07 (d, J = 9.2 Hz, 1H), 6.68 (d, J = 7.8 Hz, 1H), 6.37 (d, J = 1.5 Hz, 1H), 6.20 (s, 1H), 3.93-3.77 (m, 2H), 3.64 (s, 2H), 3.31-3.20 (m, 6H), 2.59 (s, 3H), 2.28-2.22 (m, 1H), 1.88 (m, 5H), 1.61 (d, J = 12.1Hz, 3H), 1.38 (s, 2H), 1.32-1.16 (m, 3H). MS (ESI, m/e) [M+1] + 780.2.

1228779-96-1, As the paragraph descriping shows that 1228779-96-1 is playing an increasingly important role.

Reference£º
Patent; BEIGENE, LTD.; GUO, Yunhang; XUE, Hai; WANG, Zhiwei; SUN, Hanzi; (493 pag.)WO2019/210828; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

108-55-4, Dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Curcumin 8 (100 mg, 0.27 mmol) and glutaric anhydride (31 mg, 0.27 mmol) were dissolved in toluene (15 ml). DMAP (39 mg, 0.32 mmol) was added followed by TEA (150 L, 1 mmol). The reaction mixture was stirred refluxed under inert gas for 6 h. The solvent was evaporated under vacuum. The orange precipitate was re-dissolved in ethyl acetate (50 mL) and washed with 1M HCl (5 mL). The organic phase was extracted, and the solvent was removed and dried. The crude product was purified via column chromatography using CH2Cl2:CH3OH (95:5 (v/v) as eluent. MS (ESI) [C26H26O9]: Calcd: 482.4792 Found: 483.2623 [M + H]+ and 505.2484 [M + Na]+. 1HNMR (CDCl3, 400 MHz, delta ppm): 2.08-2.11 (m, 2H), 2.55 (t, J =11.1Hz, 2H), 2.69 (t, J = 10.8, 2H), 3.86 (s, 3H), 3.93 (s, 3H), 5.81 (s, 2H), 6.44-6.55 (m, 3H), 6.91 (d, 1H), 7.09-7.61 (m, 7H). 13C NMR (CDCl3, 100 MHz, delta ppm): 19.99, 32.22, 32.74, 55.88, 101.42, 101.96, 109.72, 111.52, 114.91, 120.91, 122.24, 123.28, 124.27, 127.00, 134.15, 139.39, 140.96, 141.18, 146.65, 148.54, 151.60, 170.84, 175.56, 181.79, 184.64., 108-55-4

108-55-4 Dihydro-2H-pyran-2,6(3H)-dione 7940, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Darwish, Shaban; Mozaffari, Saghar; Parang, Keykavous; Tiwari, Rakesh; Tetrahedron Letters; vol. 58; 49; (2017); p. 4617 – 4622;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

85064-61-5, Tetrahydropyranyl-4-acetic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

85064-61-5, Example 13 To a mixture of tetrahydro-2H-pyran-4-ylacetic acid (89 mg), N,N-dimethyl formamide (1 muL), and dichloromethane (1 mL) was added oxalylchloride (54 muL), and the mixture was stirred at room temperature for 2 hours. The reaction liquid was concentrated under reduced pressure, and then toluene (1 mL) was added thereto, followed by further concentration under reduced pressure, to obtain crude tetrahydro-2H-pyran-4-yl acetyl chloride.

As the paragraph descriping shows that 85064-61-5 is playing an increasingly important role.

Reference£º
Patent; Astellas Pharma Inc.; US2011/53912; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

14774-37-9, Tetrahydropyran-4-methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of (3,3-difluorocyclobutyl)methanol (4.0 g, 32.8 mmol) in dichloromethane (109 ml) at room temperature was added Dess-Martin Periodinane (16.7 g, 39.3 mmol). After 2 h, the reaction was diluted with two volumes of ether and treated with sodiumthiosulfate (32 g) in water (160 mL). After stirring at room temperature for 10 min, the layers were separated. The ethereal was washed with saturated sodium bicarbonate (2X), dried over magnesium sulfate, and filtered. The resulting solution was concentrated via distillation of the solvent through a short path distillation apparatus. The distillation was discontinued when 6.56 g remained in the boiling flask. Integration of the 1H NMR showed product as a 28.4 wt% solution in diethyl ether (1.86 g, 47% yield). The material was directly used without further concentration, 14774-37-9

The synthetic route of 14774-37-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Degnan, Andrew P.; Maxwell, Darrell; Balakrishnan, Anand; Brown, Jeffrey M.; Easton, Amy; Gulianello, Michael; Hanumegowda, Umesh; Hill-Drzewi, Melissa; Miller, Regina; Santone, Kenneth S.; Senapati, Arun; Shields, Eric E.; Sivarao, Digavalli V.; Westphal, Ryan; Whiterock, Valerie J.; Zhuo, Xiaoliang; Bronson, Joanne J.; Macor, John E.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 24; (2016); p. 5871 – 5876;,
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.36838-71-8,4-Methylenetetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.,36838-71-8

Step B: Preparation of l ,l-dichloro-7-oxaspiror3.51nonan-2-one: Zinc was activated according to a published procedure (Synthesis 1971 ; 415). Hydrated copper sulfate (14 g) was dissolved in water (150 mL) and added to zinc dust (60 g). The mixture was stirred for 2 hours under nitrogen. The activated zinc was isolated by filtration, washed with acetone and dried in a vacuum oven at 100 C prior to use. The solution of 4- methylenetetrahydro-2H-pyran from Step A was dried with sodium sulfate and magnesium sulfate and filtered through Celite (washing the cake with ether). This removed some orange solids which had precipitated. A solution of trichloroacetyl chloride (5.00 g; 27.5 mmol) in dry ether (250 mL) was added slowly (over 4 hours) to a stirred refluxing mixture of the 4-methylenetetrahydro-2H-pyran in dry ether (250 mL) and the activated zinc (5.00 g; 76.5 mmol) under nitrogen. The mixture was stirred for 16 hours at reflux. The solution was filtered through Celite and concentrated under reduced pressure. The material was purified by chromatography on silica gel, eluting with 10: 1 hexane/ethyl acetate to give impure product (160 mg) as a colorless oil which was continued directly on to the next step.

As the paragraph descriping shows that 36838-71-8 is playing an increasingly important role.

Reference£º
Patent; ARRAY BIOPHARMA INC.; BOYS, Mark Laurence; BURGESS, Laurence, E.; GRONEBERG, Robert, D.; HARVEY, Darren, M.; HUANG, Lily; KERCHER, Timothy; KRASER, Christopher, F.; LAIRD, Ellen; TARLTON, Eugene; ZHAO, Qian; WO2011/130146; (2011); 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

61363-56-2, EXAMPLE 28 5-(4-chloro-3-nitrophenyl)-5,10-dihydro-1H,3H-dipyrano[3,4-b:4,3-e]pyridine-4,6(7H,9H)-dione A mixture of tetrahydropyran-3,5-dione (Terasawa, J. Org. Chem. (1977), 42, 1163-1169) (0.27 g, 2.4 mmol), 4-chloro-3-nitrobenzaldehyde (0.54 g, 2.9 mmol) and the product from Example 11C (0.27 g, 2.4 mmol) in ethanol (3 mL) was heated to 80 C. for 60 hours and then allowed to stand at ambient temperature for 5 hours. The solid was collected by filtration, washed with ethanol, dissolved in 1:1 methanol/methylene chloride, filtered, heated on steam bath (replacing the methylene chloride with methanol and concentrating the mixture to approximately 5 mL) and allowed to stand at ambient temperature for 2 hours. The resulting solid was collected by filtration, washed with methanol and dried to provide the title compound (0.061 g). mp>260; MS (ESI(+)) m/z 377 (M+H)+; MS (ESI(-)) m/z 375 (M-H)-; 1H NMR (DMSO-d6) delta 4.06 (s, 4H), 4.51 (AB q, 4H), 5.02 (s, 1H), 7.54 (dd, 1H), 7.68 (d, 1H), 7.79 (d, 1H), 10.18 (bs, 1H); Anal. Calcd for C17H13N2O6Cl: C, 54.20; H, 3.48; N, 7.44. Found: C, 53.84; H, 3.81; N, 7.14.

The synthetic route of 61363-56-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Abbott Laboratories; US6191140; (2001); B1;,
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.

Step A: Preparation of Intermediate 4-(4-Bromophenylthio)-tetrahydro-2H-pyran.To a solution of 4-bromobenzenethiol (300 mg, 1.60 mmol) in DMF (3 mL) was added sodium hydride (60% dispersion in mineral oil) (95 mg, 2.38 mmol) and 4-bromo-tetrahydro- 2H-pyran (458 mg, 1.75 mmol). The resulting mixture was stirred for 18 h at room temperature. The reaction was diluted with water and extracted twice with EtOAc. Purification by flash chromatography on silica gel (0-5% EtOAc in hexane) yielded the title compound (340 mg,78%) as a clear oil. 1H NMR (400 MHz, CDCl3) delta ppm 1.60 – 1.76 (m, 2 H), 1.92 (dd, J = 11.87, 1.52 Hz, 2 H), 3.20 – 3.33 (m, 1 H), 3.39 – 3.51 (m, 2 H), 3.93 – 4.05 (m, 2 H), 7.28 – 7.34(m, 2 H), 7.42 – 7.49 (m, 2 H)., 25637-16-5

As the paragraph descriping shows that 25637-16-5 is playing an increasingly important role.

Reference£º
Patent; ARENA PHARMACEUTICALS, INC.; WO2008/48609; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics