Day: September 16, 2020

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.

4,4?-Di-tert-butyl-2,2?-bipyridine (8.05 mg, 0.03 mmol) and 1,2-dimethoxyethane- dichloronickel (1:1) (5.49 mg, 0.025 mmol) were charged under argon in a flask and suspended in dry 1,2-dimethoxyethane(2 ml). This mixture was sonicated for 5 mm. In a separated microwave vial under argon Iridium( 1+), [4,4?-bis( 1,1 -dimethylethyl)-2,2?-bipyridine-icNl ,icNl ?]bis [3 ,5-difluoro-2- [5-(trifluoromethyl)-2-pyridinyl-icN]phenyl-icC]-, (OC-6-33)-, hexafluorophosphate(1-) (1:1) (CAS 870987-63-6) (5.61 mg,5.00 jimol), N-[5-(7-bromo-4-oxoquinazolin-3 (4H)-yl)-2-(trifluoromethoxy)phenyl] -1 -(4-methylpiperazin-1 -yl)cyclopropanecarboxamide (56.6 mg, 100 jimol), and lithium hydroxide (4.79 mg,200 jimol) were dissolved in 1,2-dimethoxyethane (0.6 ml) and 4-bromotetrahydro-2H-pyran (17 jil, 150 jimol) and 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane (31 jil, 100 jimol) were added under argon. 0.4 ml of the solution of the first flask (catalyst mix) was added to the microwave vial mixture and an argon stream was passed through the resulting mixture for 10 mm. The reaction mixture was irradiated with one 34 W blue LED lamp in the EvoluChemTM PhotoChemistry Device using the 8 x 2 mL vialrack which contains an incorportated fan for cooling to maintain experiment at room temperature. The reaction mixture was then allowed to stir in the device for 15 hours. The reaction mixture was then charged completely on a silica gel column and a chromatographic separation was performed with a gradient of dichloromethane/methanol from 100:0 to 90:10. The material obtained was then purified by preparative RP-HPLC on a 125x30mm with acetonitrile/water (0.2% ammonia) to obtain 25.5 mg (97 % purity, 43 % yield) of the title product.LC-MS (Method 6): R = 1.18 mm; MS (ESIpos): m/z = 572 [M+H]1HNMR (400 MHz, DMSO-d6) [ppm]: -0.008 (2.71), 0.008 (2.39), 1.102 (1.40), 1.115 (3.81), 1.123(4.40), 1.132 (2.09), 1.235 (2.04), 1.245 (4.39), 1.252 (3.56), 1.265 (1.45), 1.714 (0.41), 1.736 (1.31),1.747 (1.12), 1.764 (3.86), 1.774 (5.09), 1.787 (3.43), 1.795 (3.34), 2.157 (0.78), 2.195 (16.00), 2.328(0.72), 2.332 (0.60), 2.366 (0.69), 2.454 (6.05), 2.670 (0.59), 2.980 (0.65), 2.992 (0.73), 3.004 (1.08),3.018 (0.76), 3.030 (0.50), 3.449 (1.27), 3.460 (1.13), 3.477 (2.36), 3.485 (2.44), 3.504 (1.21), 3.512(1.41), 3.972 (2.94), 3.979 (2.01), 3.998 (2.13), 7.366 (2.14), 7.372 (2.14), 7.388 (2.37), 7.394 (2.50),7.531 (2.02), 7.535 (2.22), 7.552 (2.12), 7.555 (2.45), 7.597 (4.28), 7.675 (1.83), 7.679 (1.89), 7.697(1.67), 7.701 (1.58), 8.122 (3.87), 8.142 (3.56), 8.346 (8.33), 8.356 (0.44), 8.582 (3.80), 8.588 (3.82), 10.651 (3.83)., 25637-16-5

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

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; JIMENEZ, NUNEZ, Eloisa; BORISSOFF, Julian; HAHN, Michael; DIETZ, Lisa; ZDENKA, GAUGAZ, Fabienne; BENDER, Eckhard; LANG, Dieter; GIESE, Anja; THEDE, Kai; ZORN, Ludwig; BOULTADAKIS ARAPINIS, Melissa; (190 pag.)WO2019/63708; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

156002-64-1, Methyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Lithium hydroxide monohydrate (151.7 mmol), as a solution indistilled water (79.5 mL, 1.9 M), was added to a solution of the ester (7.59 mmol) in THF (79.5 mL, 0.1 M) at room temperature in air and stirred at 60 C for 90 min. The mixture was cooled to room temperature, acidified to pH 0 with 1M HCl and partitioned with EtOAc (20 mL). The aqueous layer was extracted with EtOAc (20 mL) and the organic layer was washed with brine (20 mL), dried (MgSO4), filtered, and concentrated under vacuum to give the desired compound, which was taken forward without purification., 156002-64-1

156002-64-1 Methyl 2-(tetrahydro-2H-pyran-4-yl)acetate 46738768, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Shouksmith, Andrew E.; Evans, Laura E.; Tweddle, Deborah A.; Miller, Duncan C.; Willmore, Elaine; Newell, David R.; Golding, Bernard T.; Griffin, Roger J.; Australian Journal of Chemistry; vol. 68; 4; (2015); p. 660 – 679;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

4295-99-2, 4-Cyanotetrahydro-4H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4295-99-2

[00312] KHMDS 1 M in THF (0.758 mL) was added dropwise to a mixture of 5-bromo-6- chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 44.2, 100 mg, 0.253 mmol) and tetrahydro-2 h-pyran-4-carbonitrile (42.1 mg, 0.379 mmol) in THF (2.5 mL), under a nitrogen atmosphere. The RM was stirred at -70C for 1 h, and allowed to warm to RT overnight. The RM was quenched with water and the solvent was evaporated off under reduced pressure to afford 5- bromo-6-(4-cyanotetrahydro-2 h-pyran-4-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide, of which (50 mg, 0.106 mmol), Pd(Ph3P)4 (18 mg, 0.016 mmol), pyrimidin-5-ylboronic acid (20 mg, 0.159 mmol), K3PO4 (68 mg, 0.319 mmol) and toluene (1.3 mL) were added to a vial, which was sealed, evacuated / purged with argon. The RM was stirred at 110C for 3 h, diluted with MeOH, filtered through a cartridge PL-Thiol MP-Resin and concentrated the combined filtrates were evaporated to dryness under reduced pressure. The crude product was purified by preparative SFC (Column 2-EP, gradient: 6% to 11 % in 6 min) and lyophilized to afford an off- white powder. UPLC-MS (Condition 2) tR = 1.2 min, m/z = 469.9 [M+H]+; XH-NMR (600 MHz, DMSO-d6) delta ppm 2.00 (d, J=13.55 Hz, 2 H) 2.40 (td, J=13.08, 3.95 Hz, 2 H) 3.52 (t, J=12.14 Hz, 2 H) 3.94 (d, J=8.66 Hz, 2 H) 7.39 (d, J=8.66 Hz, 2 H) 7.86 (d, J=8.85 Hz, 2 H) 8.30 (s, 1 H) 8.96 (s, 2 H) 9.23 (d, J=1.13 Hz, 1 H) 9.32 (s, 1 H) 10.67 (s, 1 H).

The synthetic route of 4295-99-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; FURET, Pascal; GROTZFELD, Robert Martin; JONES, Darryl Brynley; MANLEY, Paul; MARZINZIK, Andreas; MOUSSAOUI, Saliha; PELLE, Xavier Francois Andre; SALEM, Bahaa; SCHOEPFER, Joseph; WO2013/171641; (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.101691-94-5,4-(Iodomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

101691-94-5, Reference Example 3 methyl 2-[1-methyl-5-(methylsulfanyl)-1H-pyrazol-3-yl]-3-(tetrahydro-2H-pyran-4-yl)propanoate [Show Image] To a solution of diisopropylamine (4.0 mL) in tetrahydrofuran (60 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 methyl [1-methyl-5-(methylsulfanyl)-1H-pyrazol-3-yl]acetate (4.68 g) in tetrahydrofuran (5 mL) was slowly added thereto. The reaction mixture was stirred at – 70C for 15 min, and 4-(iodomethyl)tetrahydro-2H-pyran (5.80 g) was added thereto. 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 (2.57 g, yield 37%) as a pale-yellow oil from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS:299(MH+).

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

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP2266983; (2010); 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

To a solution of tetrahydro-2H-pyran-4-ol (20 g ) in tetrahydrofuran (150 mL) and triethylamine (28.5 mL) is slowly added methanesulfonyl chloride (15.5 mL), while keeping the temperature below 30C. The mixture is stirred for 1 2 hours at room temperature. The precipitate is filtered off and washed twice with tetrahydrofuran. The combined organic phases are concentrated and partitioned between ethyl acetate and water. The organic phase is dried (Na2SO4) and concentrated to give the title compound. Yield: 29.4 g; TLC: rf = 0.36 (silicagel, petrole ether/ethyl acetate 1 :1 ); Mass spectrum (ESI+): m/z = 198 [M+NH4]+., 2081-44-9

2081-44-9 Tetrahydro-2H-pyran-4-ol 74956, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; WO2013/144097; (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.103260-44-2,Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate,as a common compound, the synthetic route is as follows.

Preparatory Example 33 4-Tetrahydropyranylacetic acid STR234 20 ml of methanol, 10 ml of water and 1 g of sodium hydroxide were added to 0.9 g of ethyl 4-tetrahydropyranylacetate and agitated at 80¡ã C. for 1 hour. The solvent was removed by distillation, to which water was added. After washing with ethyl acetate, a hydrochloric acid aqueous solution was added to the resultant aqueous phase to an extent of pH of 3, followed by extraction with chloroform under salting-out conditions and drying with anhydrous magnesium sulfate. This was removed by filtration and the solvent was distilled off, thereby obtaining 0.87 g of a crude intended compound. 1 H-NMR(CDCl3) delta:1.0-2.4(m,5H), 2.28(bd,J=6.5 Hz,2H), 3.37(td,J=11.5 Hz,2.9 Hz,2H), 3.7-4.1(m,2H), 7.85(bs,1H), 103260-44-2

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

Reference£º
Patent; Eisai Co., Ltd.; US5221671; (1993); A;,
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.

Step 2: Synthesis of compound B3Prepared as described by adaptation of the following literature reference: Radziszewski, J.G. et al. J. Am. Chem. Soc. 1993, 115, 8401.To a solution of 97 g (810 mmol) of compound B2 in 2-methyltetrahydrofuran (190 mL) are added 165 mL of 50% aqueous 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 aqueous HC1 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 compound B3 as white crystalline solid. Yield: 99%, ES-MS: m/z 271 [M+H]; ]H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.19 – 1.35 (2 H, m), 1.54 – 1.63 (2 H, m), 1.85 – 2.02 (1 H, m), 2.45 (3 H, s), 3.28 – 3.39 (2 H, m), 3.86 (2H, d, J=6.60 Hz), 3.93 (2 H, dd, J=11.37, 4.52 Hz), 7.35 (2 H, d, J=9.29 Hz), 7.78 (2 H, d, J=8.31 Hz), 14774-37-9

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; ZINDELL, Renee, M.; ERMANN, Monika; WO2011/109324; (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.14774-36-8,(Tetrahydropyran-3-yl)methanol,as a common compound, the synthetic route is as follows.

Intermediate 13: 3-(Bromomethyl)tetrahvdro-2H-pyranTo tetrahydro-2H-pyran-3-ylmethanol (1g) in dry dichloromethane (28 ml) at 0C and under nitrogen, was added triethylamine (2.7 ml) in one go, followed by methanesulphonyl chloride (0.87 ml) dropwise over 1 minute. The reaction was allowed to warm to room temperature and left at this temperature overnight. The reaction mixture was diluted with dichloromethane (20 ml) and washed with saturated aqueous sodium bicarbonate (20 ml). The organic layer was passed through a hydrophobic frit to dry and concentrated in vacuo to yield a yellow oil., 14774-36-8

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

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/101867; (2008); 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

Add Intermediate V4 (36.2g, 47mmol, 1.0eq) to the 1000mL reaction flask,Intermediate VM4 (22.3g, 71mmol, 1.5eq) and 600mL dichloromethane,Stir to dissolve, then add DCC (17.4g, 85mmol, 1.8eq) and 3.6g DMAP, warm to 30-35 reaction, TLC monitor the reaction.After the reaction was completed, 400 mL of 10% acetic acid aqueous solution was added and stirred for 30 min to separate the organic phase. The organic phase was washed with saturated aqueous sodium bicarbonate solution (300 mL ¡Á 1), saturated aqueous sodium chloride solution (300 mL ¡Á 1) and dried over anhydrous sodium sulfate. Filter with suction and concentrate the filtrate under reduced pressure to obtain a crude solid. This crude product was recrystallized with 500 mL of ethyl acetate and n-hexane (1: 1) to obtain 44.1 g of solid product V5. Yield: 89%., 1228779-96-1

The synthetic route of 1228779-96-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Nantong Changyou Pharmaceutical Technology Co., Ltd.; Li Zebiao; Chen Dan; Wu Hongdang; Xu Xiaohong; Lin Yanfeng; (9 pag.)CN110878098; (2020); A;,
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.

Compound 9-3 was dissolved in dichloromethane,Add (3 eq) EDCI, (0.3 eq) DMAP,After stirring at room temperature for half an hour, compound 1-5 (0.8 eq) was added.It is then reacted at room temperature for 6-8 hours. After the reaction is completed, the reaction is quenched with water.Extract three times with dichloromethane, and combine the organic phases with saturated brine.After drying anhydrous sodium sulfate, mix the sample on the column.CH2Cl2: MeOH = 100:1 to 25:1 gave compound S9.

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

Reference£º
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhang Ao; Tan Wenfu; Liu Xiaohua; Huang Wenjing; Zhang Yu; Yang Jun; (37 pag.)CN110143974; (2019); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics