Brief introduction of 1194-16-7

1194-16-7, As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

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

In a 50 mL round bottomed flask, 2,2-dimethyldihydro-2/-/-pyran-4(3/7)-one (0.3 g, 2.3 mmol) was dissolved in water (15 mL) along with sodium metabisulfite (0.22 g, 1.17 mmol). The mixture was allowed to stir at rt for 1 h and N1-benzyl-N1-isopentyl-N2-methylethane-1,2-diamine dihydrochloride (0.72 g, 2.3 mmol) and DIPEA (1.6 mL, 9.4 mmol) were added. The mixture was stirred for 2 h and potassium cyanide (0.243 g, 3.7 mmol) was added to the reaction mixture. The reaction was stirred at rt until full conversion was achieved (12 days). The colourless solution was extracted with ethyl acetate and the combined organic phases were washed with NaHCC>3, dried over MgSC>4, filtered and concentrated to dryness to give the title compound as yellow oil (0.65 g, yield 75%). 1H NMR (400 MHz, CDCl3) delta ppm: 7.41 – 7.13 (m, 5H), 3.83 – 3.77 (m, 2H), 3.58 (s, 2H), 2.61 – 2.41 (m, 4H), 2.23 (s, 3H), 2.02 – 1.93 (m, 2H), 1.69 – 1.51 (m, 5H), 1.49 – 1.39 (m, 2H), 1.38 (s, 3H), 1.23 (s, 3H), 0.86 (d, J = 6.6 Hz, 6H)

1194-16-7, As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; ALMANSA-ROSALES, Carmen; GARCIA-LOPEZ, Monica; RODRIGUEZ ESCRICH, Sergio; (158 pag.)WO2018/153546; (2018); A1;,
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Analyzing the synthesis route of 1194-16-7

1194-16-7, As the paragraph descriping shows that 1194-16-7 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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

To a stirred solution of 2,2-dimethyltetrahydro-4H-pyran-4-one (2 g, 20 mmol) in MeOH (40 mL) and H2O (5 mL) was added ammonium formate (10.33 g, 160 mmol) and pallidum on carbon (0.5 g). The reaction was stirred under atmospheric hydrogen atmosphere for 5 h. The reaction mixture was filtered through bed of celite and washed with methanol. The resulting filtrate was concentrated under reduced pressure to afford 2,2-dimethyltetrahydro-2H-pyran-4-amine (2.5 g, 85%) as a colourless gummy material. (1S,4S)-4-((2-((2,2-Dimethyltetrahydro-2H-pyran-4-ylamino)-5-nitropyrimidin-4-yl)amino)cyclohexane-1-carboxamide.

1194-16-7, As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

Reference£º
Patent; Celgene Corporation; CANAN, Stacie S.; HAWRYLUK, Natalie Anne; WITTY, Michael John; (74 pag.)US2017/348315; (2017); A1;,
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Some tips on 1194-16-7

The synthetic route of 1194-16-7 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.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

[00660] Synthesis of compound 112.2. Into a 100-mL 3-necked round-bottom flask under nitrogen were added compound 112.1 (3 g, 23.41 mmol, 1.00 equiv), ethyl 2-cyanoacetate (2.9 g, 25.64 mmol, 1.10 equiv), S (3.0 g) and morpholine (0.75 g) in 50 mL of dry ethanol. The resulting mixture was stirred overnight at 50 C. Upon completion of the reaction solvent was removed under vacuum and crude was purified via flash column chromatography to afford 5.6 g (94%) of compound 112.2 as a yellow solid., 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; NIMBUS IRIS, INC.; CHAUDHARY, Divya; KAPELLER-LIBERMANN, Rosana; WO2014/194242; (2014); A2;,
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Downstream synthetic route of 1194-16-7

1194-16-7, 1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various.

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

2,2-Dimethyltetrahydropyran-4-one (5.Og, 32.0 mmol, see Preparation 3) is solved in methanol (4.7 ml) and carbon disulfide (4.7 ml, 48.8 mmol) is added in one portion. Malononitrile (2.6g, 39.0 mmol) is added portionwise and, finally, triethylamine (1.95 ml). The reaction mixture is stirred at room temperature for 48h. An orange precipitate is formed, which is filtered (3.9Og) and is consistent with the desired compound. From the liquid phase, 0.89g more of 6-amino-3,3-dimethyl-8-thioxo-4,8- dihydro-1H,3H-thiopyrano[3,4-c]pyran-5-carbonitrile were isolated by flash chromatography, eluting first with CH2CI2 and next with the mixture of solvents CH2CI2: MeOH 98:2. Yield= 48%. 1H NMR (200 MHz, CDCI3) delta ppm 1.30 (s, 6 H), 2.62 (s, 2 H), 4.66 (s, 2 H), 7.91 (s, 2 H)

1194-16-7, 1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; ALMIRALL PRODESFARMA, S.A.; WO2006/58723; (2006); A1;,
Tetrahydropyran – Wikipedia
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Simple exploration of 1194-16-7

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

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;,
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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,1194-16-7

To a solution of 2,2-dimethyltetrahydro- 4H-pyran-4-one (1.0 g, 7.8 mmol, 1.0 eq) in toluene (10 mL) was added morpholine (1.0 g,11.7 mmol, 1.0 mL, 1.5 eq) and PTSA (134 mg, 780 imol, 0.1 eq). The mixture was stirred at110C for 12 hours. The reaction mixture was concentrated under reduced pressure to remove solvent to give 1.3 g of cmde compound I-i as a yellow oil, which was used in the next step without further purification.

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

Reference£º
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (2018); A1;,
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Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 1194-16-7

1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various.

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

(0127) To a suspension of hexane-washed NaH (0.72 g, 60% in mineral oil) in tetrahydrofuran (30 ml) was added a solution of 2,2-dimethyldihydro-2H-pyran-4(3H)-one (2.0 g) in tetrahydrofuran (20 ml). The suspension was stirred at room temperature for 30 minutes. The dimethylcarbonate (6.31 ml) was added dropwise by syringe. The mixture was heated to reflux for 4 h. LC/MS showed the expected product as the major product. The mixture was acidified with 5% HCl and extracted with dichloromethane (100 ml¡Á3) and washed with water, brine and dried over Na2SO4. After evaporation, the crude product was loaded on a column and eluted with 10% ethyl acetate in hexane to give the product.

1194-16-7 2,2-Dimethyltetrahydropyran-4-one 1738159, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; AbbVie Inc.; Catron, Nathaniel; Lindley, David; Miller, Jonathan M.; Schmitt, Eric A.; Tong, Ping; US10213433; (2019); B2;,
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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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Tetrahydropyran – an overview | ScienceDirect Topics