Analyzing the synthesis route of 4295-99-2

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.

a 4-[[4-(2-Hydroxyethyl)phenyl]methyl]tetrahydropyran-4-carbonitrile Obtained by operating as in example 87a, from 6.3 g (62.2 mmoles) of diisopropylamine in 104 ml of tetrahydrofuran, 38.7 ml (62.0 mmoles) of a 1.6M solution of n-butyllithium in hexane, 9.3 g of 1,3-dimethylimidazolidin-2-one, 8.8 g (56.7 mmoles) of 2,3,5,6-tetrahydro-4H-pyran-4-carbonitrile (prepared according to Gibson C. S. and Johnson J. D. A., J. Chem. Soc. (1930), 2525-30) in 93 ml tetrahydrofuran and 17.7 g (62 mmoles) of the compound prepared in example 26a. After purification by chromatography on a column of silica in a hexane-ethyl acetate (1:1) mixture, there is obtained 10.5 g (yield=75.5%) oil. I.R. (film): nu (OH)=3400 cm-1; (C N)=2220 cm-1. N.M.R. (CDCl3): delta=1.55 (1H,s, exchangeable with D2 O); 1.6-1.9 (4H,m); 2.8 (2H,s); 2.8 (2H,t, J=6.75 Hz); 3.4-4.2 (6H,m); 7.1 (4H,s).

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

Reference£º
Patent; Lipha Lyonnaise Industrielle Pharmaceutique; US5387709; (1995); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 4295-99-2

4295-99-2 4-Cyanotetrahydro-4H-pyran 11815837, aTetrahydropyrans compound, is more and more widely used in various fields.

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

Preparation of Starting Materials Required C-(4-Methyltetrahydropyran-4-yl)methylamine A mixture of tetrahydropyran-4-carbonitrile (5.00 g) and THF (50 ml) was admixed at 0 C. with lithium hexamethyldisilazide (1 M, 63 ml), and, after 90 minutes, methyl iodide (4.26 ml) was added dropwise with good cooling. After 12 hours, the reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. The residue was dissolved in THF (200 ml), and lithium aluminum hydride (3.79 g) was added. The mixture was boiled at reflux for 6 hours, Water (3.8 ml) and then sodium hydroxide solution (40%; 3.8 ml) were cautiously added dropwise to the cooled suspension. The precipitate was filtered off and the filtrate was concentrated. This afforded the product with the molecular weight of 129.20 (C7H15NO); MS (ESI): 130 (M+H+).

4295-99-2 4-Cyanotetrahydro-4H-pyran 11815837, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; SANOFI; US2012/15936; (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.

Ethyl tetrahydro-2H-pyran-4-carbimidate hydrochloride (1.646 g, 8.50 mmol) was suspended in DCM (21.25 mL) and cooled to 0 C. Pyridine (3.09 mL, 38.2 mmol) was added and the solution was stirred for 15 min. Ethyl chloroformate (1.384 g, 12.75 mmol) was added dropwise. The reaction mixture was allowed to warm to RT and stir overnight. The reaction mixture was diluted with 50 % hexane/EtOAc and the resulting suspension was filtered through a plug of diatomaceous earth. The filtrate was concentrated under reduced pressure and the residue dried under high vacuum for several hours to yield ethyl N-ethoxycarbonyltetrahydro-2H-pyran- 4-carbimidate (1.80 g, 92 %). H NMR (400 MHz, DMSO-d6): delta 4.12 (m, 2 H), 4.07 (m, 2 H), 3.85-3.83 (m, 2 H), 3.31-3.24 (m, 2 H), 2.69-2.68 (m, 1 H), 1.69-1.68 (m, 4 H), 1.23 (m, 6 H)., 4295-99-2

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

Reference£º
Patent; DECIPHERA PHARMACEUTICALS, LLC; BRANDT, Gary E. L.; TELIKEPALLI, Hanumaiah; CALDWELL, Timothy Malcolm; SAMARAKOON, Thiwanka; FLYNN, Daniel L.; KAUFMAN, Michael D.; WO2014/145023; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 4295-99-2

4295-99-2 4-Cyanotetrahydro-4H-pyran 11815837, aTetrahydropyrans compound, is more and more widely used in various fields.

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

In a 1 L glass flask equipped with a stirrer, a thermometer, a gas inlet tube and a reflux condenser,100.06 g (900.3 mmol) of 4-cyanotetrahydropyran, 28.83 g (899.8 mmol) of methanol and 327 g of methylene chloride were added,While blowing hydrogen chloride gas,The mixture was allowed to react at 0 to 7 C. for 7 hours with stirring. After completion of the reaction, the reaction solution was concentrated,421 g of tert-butyl methyl ether was added, and the mixture was stirred at 3 to 10 C. for 1 hour. The obtained crystals were filtered,The filtrate was dried to obtain 157.68 g of methyl tetrahydropyran-4-imidate hydrochloride (isolation yield: 98%).

4295-99-2 4-Cyanotetrahydro-4H-pyran 11815837, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; UBE INDUSTRIES LIMITED; NAKATANI, RYO; IWATA, TOMOCHIKA; FUKUHARA, YASUAKI; MOTOYAMA, TAKAHIRO; (34 pag.)JP6183053; (2017); B2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 4295-99-2

4295-99-2, As the paragraph descriping shows that 4295-99-2 is playing an increasingly important role.

4295-99-2, 4-Cyanotetrahydro-4H-pyran 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-carbonitrile (2 g, 18.00 mmol) in tetrahydrofuran (10 mL) at 0 – 5 C was added slowly LHMDS (21.59 mL, 21.59 mmol). The mixture was stirred for 1.5 hrs at 0 C. lodomethane (3.37 mL, 54.0 mmol) was added slowly and stirring was continued for 30 min at ~0 C and then for ~2 hrs at room temperature. The mixture was cooled to 0 C and carefully diluted with 1 N aqueous hydrochloride solution (30 mL) and EtOAc (5 mL) and concentrated under reduced pressure. The residue was taken up in diethylether and the separated organic layer was washed with brine, dried over sodium sulfate, filtered off and concentrated under reduced pressure providing crude 4-methyltetrahydro-2H-pyran-4-carbonitrile (1.8 g) as an orange oil, which was directly used in the next reaction without further purification. LCMS (m/z): 126.1 [M+H]+; Retention time = 0.44 min.

4295-99-2, As the paragraph descriping shows that 4295-99-2 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; ANTONIOS-MCCREA, William R.; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; LIN, Xiaodong; MARTIN, Eric J.; PAN, Yue; PFISTER, Keith B; RENHOWE, Paul A.; SENDZIK, Martin; SUTTON, James; WAN, Lifeng; WO2012/101065; (2012); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Some tips on 4295-99-2

4295-99-2 4-Cyanotetrahydro-4H-pyran 11815837, aTetrahydropyrans compound, is more and more widely used in various fields.

4295-99-2,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.

To a solution of tetrahydro-2H-pyran-4-carbonitrile (4.85 g, 43.6 mmcl) in dry THF (41 mL), cooled at -78 C a LDA solution (30.5 mL, 1.5 M in a mixture of THF/ethylbenzene/heptane, 45.8 mmcl) was added dropwise under a nitrogen atmosphere. The mixture was stirred at -50 C for 45 mm and then it was cooled at – 78 C. A solution of tert-butyl 4-oxopiperidmne-1-carboxylate (8.69 g, 43.6 mmol) in dry THE (5.2 mL) was added and the reaction mixture was stirred at -78 00 for 2 h. Then, NH4CI sat aqueous solution was added and the mixture was extracted with EtOAc.The organic phases were combined, dried over MgSO4, filtered and concentrated to dryness. The residue was purified by flash chromatography, silica gel, gradient DCM to MeOH:DCM (1:9) to give the title compound (7.11 g, 53% yield).HPLC-MS (Method C): Ret, 3.18 mm; ESI-MS m/z, 255 (M+H-56).

4295-99-2 4-Cyanotetrahydro-4H-pyran 11815837, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; GARCIA-LOPEZ, Monica; ALMANSA-ROSALES, Carmen; LLORENTE-FERNANDEZ, Ana Virginia; CHRISTMANN, Ute; RODRIGUEZ ESCRICH, Sergio; (355 pag.)WO2017/198339; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 4295-99-2

As the paragraph descriping shows that 4295-99-2 is playing an increasingly important role.

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

To a solution of tetrahydro-2H-pyran-4-carbonitrile (10 g, 90 mmol) in dry THF (100 mL) at 0 C. was added dropwise 1.0 M NaHDMS in THF (108 mL, 108 mmol). The mixture was stirred for 1.5 h at 0 C., then treated with CH3I (38 g, 270 mmol) slowly. The mixture was stirred at RT for 16 h, then cooled to 0 C. and treated with 1 M aq. HCl (150 mL) and extracted with EtOAc (300 mL). The organic layer was washed with sat. aq. NaCl (80 mL*3), dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound as a pale yellow liquid (10 g, 87%). 1H NMR (CDCl3) delta 3.98-3.92 (m, 2H), 3.74-3.65 (m, 2H), 1.89-1.82 (m, 2H), 1.66-1.56 (m, 2H), 1.42 (s, 3H).

As the paragraph descriping shows that 4295-99-2 is playing an increasingly important role.

Reference£º
Patent; Board of Regents, The University of Texas System; LE, Kang; SOTH, Michael J.; LIU, Gang; JONES, Philip; CROSS, Jason Bryant; MCAFOOS, Timothy Joseph; CARROLL, Christopher L.; LEWIS, Richard T.; (199 pag.)US2019/308978; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 4295-99-2

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

4295-99-2, 4-Cyanotetrahydro-4H-pyran 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-carbonitrile (2 g, 18.00 mmol) in tetrahydrofiiran (10 mL) at 0 – 5 C was added slowly LHMDS (21.59 mL, 21.59 mmol). The mixture was stirred for 1.5 hrs at 0 C. Iodomethane (3.37 mL, 54.0 mmol) was added slowly and stirring was continued for 30 min at ~0 C and then for ~2 hrs at room temperature. The mixture was cooled to 0 C and carefully diluted with IN aqueous hydrochloride solution (30 mL) and EtOAc (5 mL) and concentrated under reduced pressure. The residue was taken up in diethylether and the separated organic layer was washed with brine, dried over sodium sulfate, filtered off and concentrated under reduced pressure providing crude 4-methyltetrahydro-2H-pyran-4-carbonitrile (1.8 g) as an orange oil, which was directly used in the next reaction without further purification. LCMS (m/z): 126.1 [M+H]+; Rt = 0.44 min.

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

Reference£º
Patent; NOVARTIS AG; PFISTER, Keith B; SENDZIK, Martin; WO2011/26917; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 4295-99-2

4295-99-2 4-Cyanotetrahydro-4H-pyran 11815837, aTetrahydropyrans compound, is more and more widely used in various fields.

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

A solution of tetrahydro-2H-pyran-4-carbonitrile (3.80 g, 34.2 mmol) in tetrahydrofuran (10 ml) was added dropwise over 5 min to a cold (-78 C.) solution of lithium diisopropylamine (37.5 mmol) in tetrahydrofuran (50 ml). After 30 min, a solution of 2-chloroethyl chloromethyl ether (5.00 g, 38.7 mmol) in tetrahydrofuran (10 ml) was added dropwise over 5 min and the mixture stirred for 30 min. The cooling bath was then removed and the solution was allowed to warm up to 25 C. then stirred for 1.5 h. The reaction mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic fraction was dried over anhydrous magnesium sulfate and concentrated. Filtration of the residue on silica gel (elution toluene-ethyl acetate 8:2) followed by distillation in vacuo gave 6.33 g (91% yield) of the title nitrile as a clear oil: bp 90-100 C./0.2 torr (bulb to bulb distillation, air bath temperature). 1HNMR 400 MHz (CDCl3) delta (ppm): 1.74 (2H, m, CH2), 1.92 (2H, m, CH2), 3.58 (2H, s, CH2), 3.67 (2H, t, J=5.6 Hz, CH2), 3.74 (2H, dt, J=2.3 Hz and J=12.4 Hz, CH2), 3.83 (2H, t, J=5.6 Hz, CH2), 4.0 (2H, m, OCH2).

4295-99-2 4-Cyanotetrahydro-4H-pyran 11815837, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; US2007/111984; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 4295-99-2

As the paragraph descriping shows that 4295-99-2 is playing an increasingly important role.

4295-99-2,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.

To a stirred solution of 41 tetrahydro-2H-pyran-4-carbonitrile (100 g, 0.9 mol) in 15 ethanol (500 mL) and 18 water (500 mL) at rt, was added 44 hydroxylamine hydrochloride (144 g, 2.1 mol) followed by 105 K2CO3 (136.7 g, 1.0 mol) and the mixture was heated to 70 C. for 16 h. The mixture was cooled to rt and the solvent was removed by evaporation under reduced pressure. The residue was dissolved in 10% 183 MeOH in 68 DCM and filtered. The solvent was removed by evaporation under reduced pressure to afford the 45 title compound (91 g, 70%) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) delta 1.56-1.63 (m, 4H), 2.23 (m, 1H), 3.24-3.32 (m, 2H), 3.81-3.97 (m, 2H), 5.40 (br s, 2H), 8.82 (s, 1H). [M+H]=145.3.

As the paragraph descriping shows that 4295-99-2 is playing an increasingly important role.

Reference£º
Patent; Dart NeuroScience, LLC; Bookser, Brett; Botrous, Iriny; Branstetter, Bryan; Dyck, Brian; Weinhouse, Michael; US2019/177327; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics