New learning discoveries about 53911-68-5

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

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.

A mixture of 3-(4-chlorophenyl)glutaric anhydride (0.5 g) and commercial 2-amino-4-chlorothiophenol (0.37 g) is dissolved in boiling dichloromethane (3 ml). The solution is stirred overnight at rt. The precipitate is isolated by suction filtration, washed with dichloromethane, and dried in vacuo. The crude product is recrystallised from acetone to give 0.3 g of 4-(5-chloro-2-benzothiazolyl)-3-(4-chlorophenyl)butanoic acid as colourless crystals.1H-NMR (500 MHz, DMSO-d6): delta (ppm)=2.08 (s, 3H), 2.65 (dd, J=16.0, 8.6 Hz, 1H), 2.79 (dd, J=16.0, 6.2 Hz, 1H), 3.45 (dd, J=14.8, 9.3 Hz, 1H), 3.53 (dd, J=14.8, 5.9 Hz, 1H), 3.63 (m, 1H), 7.29 (d, J=8.7 Hz, 2H), 7.33 (d, J=8.7 Hz, 2H), 7.42 (dd, J=8.6, 2.0 Hz, 1H), 7.99 (d, J=2.0 Hz, 1H), 8.02 (d, J=8.6 Hz, 1H), 12.17 (br s, 1H).13C-NMR and DEPT (125 MHz, DMSO-d6): delta (ppm)=39.27 (CH2), 40.02 (CH2), 41.17 (CH), 121.59 (CH), 123.42 (CH), 124.84 (CH), 128.11 (2CH), 129.54 (2CH), 130.70 (C), 131.12 (C), 133.35 (C), 141.45 (C), 153.38 (C), 171.82 (C), 172.42 (CO). MS (+ESI): m/z=366 (M+H).

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

New learning discoveries about 1228779-96-1

1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various.

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 13-4 was dissolved in dichloromethane, (3eq) EDCI, (0.3eq) 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 – 30:1 gave compound S13.

1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various.

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;,
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Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 101691-65-0

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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.

Step B: 7-Chloro-1-(tetrahydropyran-4-yl)methyl-1H-indole-3-carboxylic acid To a solution of 7-chloro-1H-indole-3-carboxylic acid (7.5 g, 38.0 mmol) in dimethyl-formamide (100 ml) at 10 C. under nitrogen was added sodium hydride (60% dispersion in mineral oil, 3.1 g, 76.0 mmol) portionwise over 10 mins, maintaining the temperature below 15 C. The cooling bath was removed and the suspension stirred for 90 mins. Toluene-4-sulfonic acid tetrahydropyran-4-ylmethylester (14.6 g, 53.0 mmol) was added. The mixture was heated at 50 C. with stirring for 6 h. Dimethylformamide was removed by evaporation and the residue was dissolved in water (500 ml). The emulsion was washed with dichloromethane (2*100 ml). The aqueous phase was acidified to pH 1 using 5 M hydrochloric acid and the precipitate filtered off, washed with water to neutrality and dried to afford 7-chloro-1-(tetrahydropyran-4-yl)methyl-1H-indole-3-carboxylic acid (15.0 g, 51.0 mmol) as a white solid.

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Reference£º
Patent; N.V. Organon; US2008/207598; (2008); A1;,
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Downstream synthetic route of 116131-44-3

116131-44-3 3-(Bromomethyl)tetrahydro-2H-pyran 22617257, aTetrahydropyrans compound, is more and more widely used in various.

116131-44-3, 3-(Bromomethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[00176] To a solution of 2 (100 mg, 0.452 mmol) in dry DMF (3 mL) was added NaH (60%, 27 mg, 0.678 mmol) in several portions under ice-water bath. Then the mixture was stirred at rt for 10 min and followed by addition of 15.2 (138 mg, 0.768 mmol) and then it was stirred at 50 C overnight. The mixture was diluted with water and extracted with EA for 3 times. The organic layer was combined and washed with brine for 3 times, dried over Na2S04, concentrated and then purified by prep-TLC (eluent: PE~PE/EA=2:1 ) to give the title compound (1 10 mg, 76%) as a yellow oil. 1H NMR (300 MHz, DMSO-cf6) delta ppm 7.99 (s, 1 H), 7.91 (s, 1 H), 7.87 (d, 1 H), 7.66 (d, 1 H), 4.22 (m, 2H), 3.74 (d, 1 H), 3.66 – 3.61 (m, 1 H), 3.35 (s, 1 H), 3.26 – 3.15 (m, 1 H), 2.11 (s, 1 H), 1 .64 (s, 2H), 1 .52 – 1 .39 (m, 1 H), 1 .38 – 1 .22 (m, 1 H). LC-MS: [M+H]+ = 318.92, 320.87.

116131-44-3 3-(Bromomethyl)tetrahydro-2H-pyran 22617257, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; NOVARTIS AG; HE, Feng; DU-CUNY, Lei; XIAO, Qitao; XUN, Guoliang; ZHENG, Qiangang; (152 pag.)WO2017/149463; (2017); A1;,
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Simple exploration of 25637-16-5

25637-16-5 4-Bromotetrahydropyran 13349654, aTetrahydropyrans compound, is more and more widely used in various.

25637-16-5, 4-Bromotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

10565] To 2.lh (18 mg, 0.047 mmol) was added DMF (Volume: 0.5 mE) and cesium carbonate (53.8 mg, 0.165 mmol). The reaction was stirred at room temperature for 5 minutes then 4-bromotetrahydro-2H-pyran (19.47 mg, 0.118 mmol) was added. The reaction was heated to 70 C. and stirred for 20 hours or until done by ECMS. The reaction was cooled, 0.5 ml of DMF was added, then filtered through a 0.45 nM in line filtet The DMF solution with the desired product 2.38a was used as is for the next step, assume quantitative yield. EC-MS (mlz): 466.5 [M+H], 0.79 mm.

25637-16-5 4-Bromotetrahydropyran 13349654, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Novartis AG; FU, Jiping; HAN, Wooseok; KARUR, Subramanian; LU, Peichao; PFISTER, Keith Bruce; YOUNG, Joseph Michael; (97 pag.)US2018/312507; (2018); A1;,
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Simple exploration of 2081-44-9

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

To a solution of tetrahydro-211-pyran-4-ol (5 g, 49.0 mmol) and triethylamine (5.94 g, 58.7 rnmol) in DCM (100 mL) was added mesyl chloride (16.8 g, 146.9 mmol) dropwise at 0 C under a nitrogen atmosphere. The mixture was stirred at room temperature for 5 h. Water (100 mL) was added and extracted with DCM (100 mL x 2). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the titlecompound (4 g, 45%) as a yellow solid. 1fl NMR (400 MHz, CDC13) 6 4.85 – 4.81 (m 11-I),3.90-3.87 (m, 211), 3.52 – 3.46 (m, 211), 2.99 (s, 3H), 2.01 – 1.97 (in, 2H), 1.83 – 1.80 (m,2H).

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

Reference£º
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ROMERO, F. Anthony; MAGNUSON, Steven; PASTOR, Richard; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy; CRAWFORD, Terry; ALBRECHT, Brian, K.; COTE, Alexandre; TAYLOR, Alexander, M.; LAI, Kwong Wah; CHEN, Kevin, X.; BRONNER, Sarah; ADLER, Marc; EGEN, Jackson; LIAO, Jiangpeng; WANG, Fei; CYR, Patrick; ZHU, Bing-Yan; KAUDER, Steven; (0 pag.)WO2016/86200; (2016); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 101691-65-0

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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.

To tert-butyl 3-(5-chloro-2-fluoropyridin-4-yl)phenylcarbamate (270 mg, 0.837 mmol) in DMF (3 rriL) was added slowly sodium hydride (60 wt.% in mineral oil, 40.1 mg) at 0 C. The ice bath was removed and the crude mixture was stirred for 20 min at room temperature. To the crude mixture was added (tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate (271 mg, 1.004 mmol) and stirring was continued at 40 C for 40 hrs. The reaction mixture was cooled to room temperature and diluted with EtOAc (150 mL). The mixture was washed saturated aqueous sodium bicarbonate solution (2x), water (2x) and brine (lx), dried with sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [silica gel, 24 g, EtO Ac/heptane = 0/100 to 30/70] providing [3-(5-chloro-2- fluoro-pyridin-4-yl)-phenyl]-(tetrahydro-pyran-4-ylmethyl)-carbamic acid tert-butyl ester (205 mg). LCMS (m/z): 421.2 [M+H]+; Retention time = 1.19 min.

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Reference£º
Patent; NOVARTIS AG; ANTONIOS-MCCREA, William R.; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; MARTIN, Eric J.; PAN, Yue; PFISTER, Keith B.; SENDZIK, Martin; SUTTON, James; WAN, Lifeng; WO2012/66065; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Analyzing the synthesis route of 4295-99-2

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4295-99-2,4-Cyanotetrahydro-4H-pyran,as a common compound, the synthetic route is as follows.

Preparation 46 1 -(tetrahydro-2H-pyran-4-yl)cyclopropanamine [0227] Combined tetrahydro-2H-pyran-4-carbonitrile (1.000 g, 9.00 mmol) and titanium (rV)isopropoxide (2.90 mL, 9.90 mmol) in ether (45.0 mL), then ethylmagnesium bromide (6.60 mL, 19.79 mmol) was added and the reaction was allowed to warm to room temperature for 1 hour. The reaction was stirred for an additional 30 minutes and boron trifluoride etherate (2.280 mL, 18.0 mmol) was added and the reaction was stirred for 2 hours. The reaction was then diluted with 10 mL water and 20 mL 1 N HC1 and extracted twice with 200 mL EtOAc. The organic layers were combined and concentrated to afford the title compound (850 mg, 53.5%) as a yellow oil.

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

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; DAVIS, Melinda; IVETAC, Anthony; JONES, Benjamin; KIRYANOV, Andre, A.; KUEHLER, Jon; LANIER, Marion; MIURA, Joanne; MURPHY, Sean; WANG, Xiaolun; WO2014/160810; (2014); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 101691-65-0

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

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

Reference Example 4: Synthesis of 7-[4-(tetrahydropyran-4-ylmethoxy)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylamine 7-(4-hydroxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylamine (the compound obtained in Reference Example 3; 295 mg) was dissolved in N,N-dimethylformamide (8 ml). Thereafter, tetrahydropyran-4-ylmethyl p-toluenesulfonate (460 mg) and cesium carbonate (556 mg) were added to the obtained solution, and the obtained mixture was stirred at 90C overnight. After the reaction solution was cooled to a room temperature, distilled water (18 ml) was added thereto. The generated precipitate was collected by filtration, and the obtained product was then washed by successive suspension in a 20% ethanol solution, ethanol, and acetone to obtain the captioned compound (310 mg).

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

Reference£º
Patent; NIPPON KAYAKU KABUSHIKI KAISHA; EP1630165; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 1194-16-7

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

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

A solution of 2,2-dimethyltetrahydropyran-4-one (133) (115 g, 0.9 mol, 1.0 eq.) in anhydrous THF (600 mL) was cooled to -78 C and to it was added LDA (2.0 M, 538 mL, 1.08 mol, 1.2 eq.) drop wise under N2 keeping the internal temperature below -65 C. The resulting solution was stirred at -78 C for 20 min. A solution of N-phenyl- bis(trifluoromethanesulfonimide) (353 g, 0.99 mol, 1.1 eq.) in anhydrous THF (1900 mL) was added to the above solution slowly keeping the internal temperature below -65 C. The reaction mixture was warmed to room temperature slowly and stirred overnight. The reaction was quenched with saturated aqueous sodium bicarbonate solution, and extracted with MTBE (2 L X 2). The combined organic layers was washed with 10% aqueous NaOH solution (1 L X 2), brine (500 mL X 2), dried over Na2S04, filtered and concentrated to give crude title triflate product mixture as dark brown oil. The crude product was extracted with hexanes (2 L X 5) and the combined hexanes extracts was purified by column chromatography (directly loaded onto silica gel, Hexanes? 15% ethyl acetate in hexanes, R/= 0.6, visualized with KMn04 stain) to give 200 g of the triflate product mixture (134) (a mixture of 2,2-dimethyl-3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate and 6,6-dimethyl-3 ,6-dihydro-2H-pyran-4-yltrifluoromethanesulfonate ratio = 80.6: 19.4 by GCMS) as a light yellow liquid (~ 90% purity by GC-MS and 1H NMR). This was taken to the next step without further purification.; A mixture of compound 2,2-dimethyl-3 ,6-dihydro-2H-pyran-4-yltrifluoromethanesulfonate and 6,6-dimethyl-3 ,6-dihydro-2H-pyran-4-yltrifluoromethanesulfonate (134) (200 g, 0.77 mol, 1.0 eq.), bis(pinacolato)diboron (135) (195 g, 0.77 mol, 1.0 eq.), and potassium acetate (151 g, 1.54 mol, 2.0 eq.) in dioxane (2 L) was degassed for 15 min, to it was added l,l ‘-bis(diphenylphosphino)ferrocene- palladium(II)dichloride dichloromethane complex (19 g, 0.023 mol, 0.03 eq.) and the reaction mixture was degassed again for 15 min. The reaction mixture was heated to 80 C overnight, cooled, filtered through a medium fritted funnel, and washed with MTBE (300 mL X 4). The organic extracts were combined and concentrated under reduced pressure. The crude product mixture (136) was cooled using an ice bath, stirred with an overhead stirrer and to it was added aqueous 2M NaOH solution (2 L) keeping the internal temperature below 15 C. The basic aqueous solution was extracted with MTBE (250 mL X 3), and the organic extracts were discarded. The aqueous phase was cooled using an ice bath and the pH was adjusted to 3 to 5 with concentrated HC1 keeping the internal temperature below 10 C. The heterogeneous solution (off-white solid precipitated out at pH 3~5) was extracted with EtOAc (3 L and 1.5 L). The combined organic layer was washed with water (1 L), brine (1 L), dried over Na2S04, filtered and concentrated. The crude product mixture (136) was purified by columnchromatography (Hexanes? 15% ethyl acetate in hexanes, R = 0.5, visualized on KMn04) to give 125 g of 2-(2,2-dimethyl-3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-l,3,2- dioxaborolane and 2-(6,6-dimethyl-3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-l,3,2- dioxaborolane mixture (136) as a white solid (58% overall yield, >97%> purity by GCMS and 1H NMR, The ratio of regioisomers was found to be 80.4: 19.6).GCMS: >97%1H NMR (300 MHz, CDC13) delta 6.46 – 6.43 (m, 1H), 4.06 (q, 2H, J=3.0 Hz), 1.96 – 1.94 (m, 2H),1.20 (s, 12H), 1.09 (s, 6H)GCMS: 239 (M+l); calcd for Ci3H23B03: 238.13

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

Reference£º
Patent; AMGEN INC.; ALLEN, Jennifer R.; CHEN, Jian J.; FROHN, Michael J.; HU, Essa; LIU, Qingyian; PICKRELL, Alexander J.; RUMFELT, Shannon; RZASA, Robert M.; ZHONG, Wenge; WO2011/143365; (2011); A1;,
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