Day: September 3, 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.103260-44-2,Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate,as a common compound, the synthetic route is as follows.

A solution of sodium hydroxide (15.9 g, 44.06 mmol) in water (150 ml) was added dropwise to a solution of ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (15 g, 8.81 mmol) in methanol (150 ml) at a temperature of 0 C or below, and the mixture was stirred at room temperature for 15 hr. The solvent of the reaction mixture was removed by distillation under reduced pressure, and the water layer was adjusted to pH 3 by the addition of 1 M hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate, and the filtrate was concentrated under reduced pressure to give a corresponding acid as a colorless solid (12.0 g, 94%). This compound was used in the next step without further purification. Benzyl bromide (14.3 g, 83.33 mmol) was added dropwise to a suspension of this compound (10.0 g, 69.44 mmol) and anhydrous potassium carbonate (28.8 g, 208.3 mmol) in acetonitrile (100 ml) at room temperature, and the mixture was refluxed for 48 hr. The solvent of the mixture was removed by distillation under reduced pressure, the residue was diluted with water and was extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on silica gel column (hexane:ethyl acetate = 9:1) to give the tile compound as an oil (12.0 g, yield 75%). 1H-NMR (400 MHz, CDCl3): delta (ppm) 7.39-7.34 (m, 5H), 5.12 (s, 2H), 3.95-3.92 (m, 2H), 3.42-3.36 (m, 2H), 2.30 (d, J = 7.2 Hz, 2H), 2.09-1.99 (m, 1H) 1.64-1.61 (m, 2H), 1.39-1.29 (m, 2H); MS (ESI): m/z 234 (M+)., 103260-44-2

As the paragraph descriping shows that 103260-44-2 is playing an increasingly important role.

Reference£º
Patent; Meiji Seika Pharma Co., Ltd.; MORINAKA, Akihiro; MAEBASHI, Kazunori; IDA, Takashi; HIKIDA, Muneo; YAMADA, Mototsugu; ABE, Takao; EP2737900; (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.19752-84-2,Tetrahydro-2H-pyran-3-ol,as a common compound, the synthetic route is as follows.

To a solution of DIAD (2.0 equiv.) and triphenylphosphine (2.0 equiv.) in THF (0.24 M) was added tetrahydro-2H-pyran-3-ol (1.2 equiv.). The mixture was stirred for 10 min. methyl 6-(2,6-difluoro-4-hydroxyphenyl)-5-fluoropicolinate (1.0 equiv.) was added. The mixture was stirred at ambient temperature overnight. Additional triphenylphosphine (2.0 equiv.) and DIAD (2.0 equiv.) were added, and the mixture was stirred overnight. The mixture was concentrated and purified by flash chromatography over silica gel (heptanes:ethyl acetate gradient) to give methyl 6-(2,6-difluoro-4-((tetrahydro-2H-pyran-3-yl)oxy)phenyl)-5-fluoropicolinate in 39% yield. Purification was completed via chiral HPLC (EtOH/heptane)=15/85, 20 mL/min, AD column) to yield (S)-methyl 6-(2,6-difluoro-4-((tetrahydro-2H-pyran-3-yl)oxy)phenyl)-5-fluoropicolinate (18% yield, 99% ee) and (R)-methyl 6-(2,6-difluoro-4-((tetrahydro-2H-pyran-3-yl)oxy)phenyl)-5-fluoropicolinate (18% yield, 99% ee). LC/MS=368.2 (MH+), Rt=0.92 min. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.65 (ddd, J=12.81, 8.51, 4.11 Hz, 1H), 1.78-1.97 (m, 2H), 2.06-2.16 (m, 1H), 3.57-3.67 (m, 2H), 3.72-3.80 (m, 1H), 3.95 (dd, J=11.54, 2.15 Hz, 1H), 3.99-4.01 (m, 3H), 4.32 (dt, J=6.95, 3.37 Hz, 1H), 6.54-6.62 (m, 2H), 7.59-7.67 (m, 1H), 8.19-8.28 (m, 1H)., 19752-84-2

The synthetic route of 19752-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Burger, Matthew; Ding, Yu; Han, Wooseok; Nishiguchi, Gisele; Rico, Alice; Simmons, Robert Lowell; Smith, Aaron R.; Tamez, JR., Victoriano; Tanner, Huw; Wan, Lifeng; US2012/225061; (2012); 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

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 18h. The suspension is poured into a mixture of ice-water (280 mL) and aq. HCI 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, As the paragraph descriping shows that 14774-37-9 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; BINDER, Florian; DOODS, Henri; MUELLER, Stephan, Georg; NICHOLSON, Janet, Rachel; SAUER, Achim; WO2014/184327; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1228779-96-1, 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1228779-96-1, A mixture of dichloromethane (12.0 L), 2-((lH-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-(4- ((4′-chloro-5,5-dimethyl-3,4,5,6-tetrahydro[l,r-biphenyl]-2-yl)methyl) piperazin-l- yl)benzoicacid hydrochloride (600.0 g), triethylamine (299.79 g), 4- dimethylaminopyridine (180.97 g), 3-nitro-4-(((tetrahydro-2H-pyran-4- yl)methyl)amino)benzenesulfonamide (342.56 g) and N-(3-Dimethylaminopropyl)-N’- ethylcarbodiimide hydrochloride (283.97 g) was stirred at 25 to 30 degree Celsius for 8h. The reaction mixture was treated with N,N-dimethylethylenediamine (217.63 g) at 20 to 30 degree Celsius and stirred for 4h. The organic layer was washed with water (6.0 L) and concentrated under vacuum. The residue was dissolved in dichlo methane- methanol mixture (1:5) (7.2 L) and treated with acetic acid-methanol mixture (415.11 g acetic acid and 600 mL methanol) and stirred at 20 to 30 degree Celsius. The resulting slurry was cooled to 0 to 5 degree Celsius, filtered and washed with methanol (600 mL). The solid was dissolved in (9:1) mixture of dicloromethane-methanol (4.8 L) at 35 to 45 degree Celsius, diluted with methanol (1680 mL) and stirred for 8h at 20 to 30 degree Celsius. The resulting slurry was cooled to 0 to 5 degree Celsius, filtered, washed with methanol (600 mL) and the solid was dried under vacuum at 60 to 65 degree Celsius for 18 h to provide 4-(4-{ [2-(4-chlorophenyl)-4,4-dimethylcyclohex-l-en-l-yl]methyl}- piperazin-l-yl)-N-({3-nitro-4[(tetrahydro-2H-pyran-4ylmethyl)amino]- phenyl} sulfonyl)-2-(lH-pyrrolo[2,3-b]pyridin-5-yloxy)benz amide. Yield: 70.0% (600g) HPLC Purity: -99.9% 1H NMR data-(DMSO-d6): d 0.921 (s, 6H), 1.204-1.308, 1.598-1.626 (m, d, J=l l.2Hz, 4H), 1.382 (t, J=6.4Hz, 4H), 1.883 (m, 1H), 1.951 (s, 2H), 2.144 (t, br, 2H), 2.199 ( s, br, 4H), 2.754 (s, 2H), 3.073 (s, br, 4H), 3.237-3.291, 3.829-3.865 (m, dd, J=2.8, 3.2, 11.2, l l.6Hz, 6H), 6.189 (d, J=2.0Hz, 1H), 6.388 (dd, J=2.0, 3.6Hz, 1H), 6.678 (d, J=2.0, 2.4, 9.2, 9.6Hz, 1H), 7.037 (d, J=8.8Hz, 2H) 7.11 (d, J=9.2Hz, 1H), 7.34 (d, J=8.0Hz, 2H), 7.495 (m, 2H), 7.535 ( d, J=2.4Hz, 1H), 7.801 (dd, J=2.0, 2.4, 8.8, 9.2Hz, 1H), 8.038 (d, J=2.0Hz, 1H), 8.558 (d, J=2.4Hz, 1H), 8.598 (t, 1H), 11.366 (s, br, 1H), 11.679 (s, 1H).

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

Reference£º
Patent; FRESENIUS KABI ONCOLOGY LTD.; GUPTA, Chandan Kumar; DHIMAN, Navdeep; SANGHANI, Sunil; SINGH, Govind; LAHIRI, Saswata; CABRI, Walter; GUPTA, Nitin; (0 pag.)WO2020/3272; (2020); 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 1: Preparation of (3R)-5-methyl-3-r2-oxo-2{rdR)-l-phenylethyl]amino|ethyl) hexanoic acid compound (24*); [0075] A three-necked flask equipped with an addition funnel, thermometer pocket , drying tube and a mechanical stirrer, was charged with toluene (400 ml), (R)-(+)- EPO phenylethylamine (38.59 g, 0.0.319 mole) and 4-dim’ethylaminopyridine (0.358 g, 0.0029 mole). The mixture was cooled to a temperature of -50C to -60C, followed by addition of a solution of 3-isobutyl glutaric anhydride (50 g, 0.294 mole) in toluene (100 ml), over a period of 45-60 minutes, and stirring for additional 1.5-2 hours, at a temperature of -50C to -60C. The mixture was then extracted with 3.5-4.0 percent aqueous solution of NaOH (1000 ml), and the aqueous phase was washed with toluene (1 x 250 ml). The pH of the aqueous phase was adjusted to 2-2.5 by adding a solution hydrochloric acid (1-12N). The aqueous phase was further extracted with ethyl acetate (1 x 300 ml and 1 x 100 ml), followed by drying the combined ethyl acetates extracts over anhydrous sodium sulfate, and stripping off the solvents to obtain a residue. The residue was crystallized from ethyl acetate and toluene mixture to get 66 g (77.2 percent yield) of a white solid of (3R)-5-methyl-3-(2-oxo-2-{[(lR)- 1-phenylethyl] amino} ethyl) hexanoic acid with an optical purity of 99.91 percent, as measured by chiral HPLC.; Example 12: Preparation of r3RV5-me1hyl-3-f2-oxo-2(rriRVl-phenyle1hyl1ainino)ethyl’) hexanoic acid compound (24*); [0086] A three-necked flask equipped with an addition funnel, thermometer pocket, drying tube and a mechanical stirrer, was charged with toluene (100 ml), (R)-(+)- phenylethylamine (35.58 g, 0.147mole) and 4-dimethylaminopyridine (0.18 g, 0.00147 mole). The mixture was cooled to a temperature of 0-5C, followed by addition of a solution of 3-isobutyl glutaric anhydride (25 g, 0.147 mole) in toluene (25 ml), over a period of 15-20 minutes, and stirring for additional 1.5-2 hours, at a temperature of 0-5 C. The mixture was then extracted with 2.5-3 percent aqueous solution of NaOH solution (500 ml), and the aqueous phase was washed with toluene (1 x 50 ml). The pH of the aqueous phase was adjusted to 2-2.5 by adding a 1-12N solution of hydrochloric acid. The aqueous phase was further extracted with ethyl acetate (1 x 150 ml and 1 x 50 ml), followed by drying the combined ethyl acetates extracts over anhydrous sodium sulfate, and stripping off the solvents, to obtain a residue. The residue was crystallized from ethyl acetate and toluene mixture to get 29.3 g (68.5 percent yield) of a white solid of (3R)-5-methyl-3-(2-oxo-2- {[(lR)-l-phenylethyl]amino}ethyl)hexanoic acid with an optical purity of 99.34 percent, as measured by chiral HPLC., 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; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2007/35789; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

14774-36-8, (Tetrahydropyran-3-yl)methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3.4 3-Tetrahydropyranylmethyl mesylate 4 g of 3-hydroxymethyltetrahydropyran are dissolved in 10 ml of dichloromethane, then 4.12 g of triethylamine are added, the mixture is cooled to a temperature between 0 and -5 C. and a mixture of 2.9 ml of mesyl chloride and 100 ml of dichloromethane is added dropwise. When the addition is complete, the mixture is allowed to warm to room temperature and is left at this temperature for 45 min. The organic phase is then washed with water until neutral, dried over sodium sulphate and filtered, and the solvent is evaporated off. 5.9 g of product are obtained in the form of an oil.

14774-36-8, 14774-36-8 (Tetrahydropyran-3-yl)methanol 85769, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Synthelabo; US5525619; (1996); A;,
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, To a solution of tetrahydro-2H-pyran-4-ylacetic acid (35 mg) (available from Anichem) in DMF (1 ml) was added HATU (92 mg) and the mixture stirred at RT for 10 min when 6- (1 H-indol-4-yl)-1 H-indazol-4-amine (50 mg) and DIPEA (0.070 ml) were added and the mixture allowed to stand for 18 h. The mixture was blown to dryness under a stream of nitrogen and purified by MDAP (method A) to afford the title compound as a white solid, 16 mg.LCMS (method A); Rt = 2.1 min, MH+ = 375.

The synthetic route of 85064-61-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; BALDWIN, Ian Robert; DOWN, Kenneth David; FAULDER, Paul; GAINES, Simon; HAMBLIN, Julie Nicole; JONES, Katherine Louise; JONES, Paul Spencer; LE, Joelle; LUNNISS, Christopher James; PARR, Nigel James; RITCHIE, Timothy John; ROBINSON, John Edward; SIMPSON, Juliet Kay; SMETHURST, Christian Alan Paul; WO2011/67365; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1194-16-7, 2,2-Dimethyltetrahydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a suspension of (methoxymethyl)triphenylphosphonium chloride (20.06 g, 58.5 mmol) in THF (1 L) was added NaHMDS (58.5 mL, 1.0 M in THF) at -40 and stirred for 30 min, then 2,2-dimethyldihydro-2H-pyran-4(3H)-one (5 g, 39.0 mmol) in THF (20 mL) was added to the mixture at -40 . After addition, the mixture was warmed to 10 and stirred for 2 h. The mixture was quenched with saturated NH4Cl (300 mL ¡Á 2) and extracted with DCM (200 mL ¡Á 2). The combined organic layers were washed with brine (600 mL), dried over sodium sulfate and concentrated in vacuo to give the crude product. Chromatography over silica gel column eluted with (petroleum ether: EtOAc30: 1) to give the desired product as an oil.1HNMR(400MHz, CDCl3) G 5.92 (s, 0.4H) , 5.76 (s, 0.6H) , 3.61 -3.70 (m, 2H) , 3.49 -3.58 (m, 3H) , 2.23 (t, J5.5Hz, 1.3H) , 2.15 (s, 0.7H) , 1.99 (t, J5.5Hz, 0.7H) , 1.90 (s, 1.3H) , 1.13 -1.22 (m, 6H)

1194-16-7, The synthetic route of 1194-16-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; ARASAPPAN, Ashok; BUNGARD, Christopher James; FRIE, Jessica L.; HAN, Yongxin; HOYT, Scott B.; MANLEY, Peter J.; MEISSNER, Robert S.; PERKINS, James; SEBHAT, Iyassu K.; WILKENING, Robert R.; (140 pag.)WO2016/29454; (2016); A1;,
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 1: Methanesulfonic acid tetrahydro-pyran-4-yl ester To a solution of tetrahydro-2H-pyran-4-ol (25 g, 245 mmol) and triethyl amine (40.1 ml, 294 mmol) in CH2Cl2 (500 ml) at 0 C. was added dropwise methanesulfonylchloride (20.7 ml, 269 mmol) over a period of 40 min, keeping the temperature between 0-4 C. The reaction mixture was then allowed to stir at 0 C. for 1 hr. The cooling bath was removed and the mixture was stirred for another 90 mins at 25 C. The mixture was washed with water (2*125 ml), dried over anhydrous Na2SO4, filtered and concentrated under vacuum to get methanesulfonic acid tetrahydro-pyran-4-yl ester (38 g, 86%; crude) as liquid that was used in the next step without any further purification., 2081-44-9

As the paragraph descriping shows that 2081-44-9 is playing an increasingly important role.

Reference£º
Patent; Hoffmann-La Roche Inc.; GROEBKE ZBINDEN, Katrin; PINARD, Emmanuel; RYCKMANS, Thomas; (19 pag.)US2016/326144; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

103260-44-2, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 32: 2-(Tetrahydro-2/-/-pyran-4-yl)ethanolTo an ice-cold solution of lithium aluminium hydride (12.6 ml, 2.3M solution in tetrahydrofuran) in dry tetrahydrofuran (20 ml) and under nitrogen, was added a solution of ethyl tetrahydro-2/-/-pyran-4-yl acetate (5g) in dry tetrahydrofuran dropwise over 10 minutes. Following the addition the reaction was heated to reflux, overnight. The reaction was cooled and diluted with diethyl ether (100 ml). A 5M aqueous solution of sodium hydroxide (-10 ml) was added cautiously to the reaction mixture until the effervescence ceased. The formed white precipitate was filtered off. The resulting filtrate was dried over potassium carbonate, filtered and concentrated in vacuo. This yielded the title compound as a colourless oil (3.3g). MS calcd for (C7H14O2)” = 130 MS found (electrospray): (M+H)+ = 1311 H NMR (DMSO): 4.35 (1 H, t), 3.80 (2H, m), 3.43 (2H, m), 3.25 (2H, m), 1.60 (1 H, m), 1.54 (2H, m), 1.35 (2H, m), 1.13 (2H, m).

103260-44-2, 103260-44-2 Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate 2773412, aTetrahydropyrans compound, is more and more widely used in various.

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