Day: September 23, 2020

1768-64-5, 4-Chlorotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A stirred mixture of (S)-(+)-prolinol (0.4 14 g, 3.99 mmol), NiC12-glyme (0.449 g, 1.99 mmol), phenyl boronic acid (3.04 g, 24.98 mmol) and KHMDS (6.6 g, 33.3 mmol) was submitted to few cycles of vacuumlargon flow. i-PrOH (40 mL) was added and the resulting mixture was stirred at r.t. for 10 mm, then 4-chlorotetrahydropyran (1.75 mL, 16.6 mmol) wasadded dropwise. The resulting yellowish mixture was heated at 65 C for 50 h, then cooled at r.t., diluted with EtOAc (200 mL) and washed with 10% HC1 solution (30 mL), sat. NaHCO3 solution (30 mL x 2) and brine (40 mL). The organic layer was dried over Na2504, filtered and concentrated to dryness to afford a solid crude (2.5 g). Purification by typical silica gel flash chromatography using a Teledyne ISCO apparatus (Cy/TBME from 100:0 to 80:20) afforded thepure title compound (1.29 g, 48%), as a liquid. R= 2.36 mm. ?H NMR (CDC13): oe 7.40-7.28 (m,2H), 7.24-7.19 (m, 3H), 4.20-4.07 (m, 2H), 3.57 (td, 2H, J= 11.5, 2.5 Hz), 2.80 (tt, 1H, J= 11.5,4.2 Hz), 1.94-1.75 (m, 4H)., 1768-64-5

As the paragraph descriping shows that 1768-64-5 is playing an increasingly important role.

Reference£º
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; PIOMELLI, Daniele; BANDIERA, Tiziano; BERTOZZI, Fabio; NUZZI, Andrea; FIASELLA, Annalisa; PONZANO, Stefano; PAGLIUCA, Chiara; REGGIANI, Angelo Mario; WO2014/144836; (2014); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

624734-17-4, 3-Methoxydihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

624734-17-4, General procedure: Toa solution of ((3aS,5S,6aR)-5-aminohexahydro-2H-cyclopenta[b]furan-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone (119 mg, 0.33 mmol, 1 eq) in DCM at rtwas added acetic acid (0.01 mL, 0.17 mmol, 0.5 eq),3-methoxytetrahydro-4H-pyran-4-one (131 mg, 1.0 mmol, 3 eq) and sodiumtriacetoxyborohydride (355 mg, 1.67 mmol, 5 eq). After stirring overnight, saturated NaHCO3was added, the solution extracted with DCM, the organics combined, dried overMgSO4, and concentrated.Purification by chromatography (12 g) eluting with 4 to 8% methanol/DCMwith ammonia afforded compound 2a ((3aS,5S,6aR)-5-((3-methoxytetrahydro-2H-pyran-4-yl)amino)hexahydro-2H-cyclopenta[b]furan-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone(83 mg, 50%). 1H NMR (CHLOROFORM-d)d: 8.72 (br. s., 1H), 7.70 (br. s., 1H), 4.98 -5.14 (m, 1H), 4.70 – 4.89 (m, 2H),3.80 – 4.18 (m, 5H), 3.25 – 3.75 (m, 8H), 3.07 – 3.24 (m, 2H), 2.53 – 2.89 (m,1H), 2.01 – 2.48 (m, 4H), 1.39 – 1.88 (m, 5H).ESI-MS (m/z): Calculated for C23H30F3N3O4:470.2 (M+1); found: 470.2.

As the paragraph descriping shows that 624734-17-4 is playing an increasingly important role.

Reference£º
Article; Winters, Michael P.; Teleha, Christopher A.; Kang, Fu-An; McComsey, David; O’Neill, John C.; Hou, Cuifen; Kirchner, Thomas; Wang, Ping; Johnson, Dana; Sui, Zhihua; Bioorganic and Medicinal Chemistry Letters; vol. 24; 9; (2014); p. 2137 – 2140;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

125995-03-1, Atorvastatin lactone is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,125995-03-1

An authentic sample of Lactone (530mg) was dissolved in anhydrous DMF (5ML), followed by imidazole (174mg), then TBDMS chloride (371 mg). The mixture was stirred at room temperature. After 6 hours, the reaction was worked up by addition of ET20 (30ML) and water (30ML). The separated organic phase was further washed with water (2 x 20MOI), dried, and concentrated in vacuo to afford silylated lactone as a white powder (470mg, 73%). The silylated lactone (233mg) was dissolved in anhydrous dichloromethane (5ML), then COOLED TO-78C under Nitrogen. DIBAL (0. 31 ml, 1 M in toluene) was added dropwise and the mixture stirred for 10 minutes AT-78C. The mixture was then quenched by addition of 1 ml of 10% aqueous Rochelle’s salt and allowed to warm to room temperature. After addition of further DICHLOROMETHANE (10ML) and water (10MOI), the phases were separated and the organic phase dried and concentrated in vacuo. The residual oil was purified by column chromatography (50% ET20 in hexane). FTIR : 1668 CM~ (amide). Stretch at 1735CM (Lactone) no longer present. The silylated lactol (100mg) was dissolved in anhydrous THF. HF. pyridine was added (0. 1ML) at 0C and allowed to warm to room temperature. The mass was quenched with ether/and sodium bicarbonate solution. The phases separated and the aqueous phase back extracted with ether. The organic phases were combined, dried and evaporated to produce and oil (75mg). M/z 542,524, 506;’H nmr CDC13 1.3 (d, 6H), 1.6- 1.9 (m, 6H), 3.45 (2H), 3.6 (m, 2H), 3.8 (m, 1H), 5.0 (m, 1H), 6.8 (br. s 1H), 7.1 (m, 14H); 3C nmr CDCI3 91.6ppm (Lactol C); FTIR : 1652CM (Amide)

As the paragraph descriping shows that 125995-03-1 is playing an increasingly important role.

Reference£º
Patent; AVECIA LIMITED; WO2005/12246; (2005); 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.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

To a mixed solution of 62 (7.25 g, 32.5 mmol) and L12CUCI4 (16.2 mL, 0.1 M solution in THF, 1.62 mmol, 5 mol %) in THF (50 mL) at 0C was slowly added Grignard reagent ((cyclobutylmethyl)magnesium bromide) that5 was made from (bromomethyl)cyclobutane (9.69 g, 65.0 mmol) and grinded magnesium turnings (3.16 g, 130 mmol) in Et20 (50 mL). After the addition completed, stirred at 0C for 30 min and then at RT for 18 hr. The reaction was quenched by NH4Cl at 0C and stirred at RT for 20 min. Then the mixture was treated with hexanes and water. Organic phase was washed by brine, dried over Na2S04, and concentrated to give 63 (6.9 g, 100%) as a colorless oil. ‘H NMR (400 MHz, Chloroform-ri) d 4.57 (dd, J= 4.5, 2.7 Hz, 1H), 3.87 (ddd, .7= 11.1, 7.4, 3.4 Hz, 1H), 3.72 (dt, J = 9.6, 6.9 Hz, 1H), 3.56 – 3.45 (m, 1H), 3.37 (dt, J= 9.6, 6.7 Hz, 1H), 2.24 (dq, J= 15.5, 7.8 Hz, 1H), 2.10 – 1.93 (m,3H), 1.91 – 1.64 (m, 4H), 1.62 – 1.45 (m, 7H), 1.39 (q, J= 7.4 Hz, 2H), 1.25 (tdd, J= 10.0, 7.2, 3.9 Hz, 2H). 13C NMR (101 MHz, Chloroform-ri) d 98.78, 67.65, 62.28,36.79, 36.06, 30.73, 29.70, 28.32 (2C), 25.46, 23.77, 19.66, 18.43.

33821-94-2, 33821-94-2 2-(3-Bromopropoxy)tetrahydro-2H-pyran 2777988, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; TSRL, INC.; LIPKA, Elke D.; SIMON, Eric; WHITE, Andy, D.; HUTCHINGS, Kim, M.; GAN, Xinmin; (0 pag.)WO2020/6050; (2020); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1240390-36-6, tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1240390-36-6, Step 2 {(3R,4R)-4-[7-(5-Methyl-4,5-dihydro-pyridin-2-yl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester To a solution of 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (5-methyl-4,5-dihydro-pyridin-2-yl)-amide (0.071 g, 0.233 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (0.0756 g, 0.350 mmol) in dioxane (3 mL) was added diisopropylethylamine (0.122 mL, 0.699 mmol). The reaction mixture was heated at 120 C. overnight. The reaction mixture was cooled and then diluted with dichloromethane, washed with aqueous sodium carbonate, then brine, dried over anhydrous Na2SO4, filtered and concentrated. Purification by chromatography (silica, 40 g, 0 to 50% ethyl acetate in hexanes) gave {(3R,4R)-4-[7-(5-methyl-4,5-dihydro-pyridin-2-yl)-thieno[3,2-d]pyrimidin-2-ylamino]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (0.047 g, 0.097 mmol, 41.6%) as a yellow solid. LCMS m/z [M+H]=485.

As the paragraph descriping shows that 1240390-36-6 is playing an increasingly important role.

Reference£º
Patent; Hoffmann-La Roche Inc.; Chen, Shaoqing; Hermann, Johannes Cornelius; Le, Nam T.; Lucas, Matthew C.; Padilla, Fernando; US2013/178460; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1172623-99-2, tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Ruthenium chloride (45 mg) was added to a solution oftert-butyl[(2R,3S)-5-hydroxy-2-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate (15.0 g; Formula IX;Example 10) and acetic acid (15.0 mL) in acetonitrile (45.0 mL) and water (7.5 mL) at0C. Sodium bromate (4.0 g) was added slowly to the reaction mixture at 0C to 5C overS hours, and then the mixture was stirred for 16 hours at -5C to 5C. After completion ofthe reaction, IPA (15 mL) was added over 25 minutes at 0C to 5C, and then the mixture was stirred for 15 minutes. Water (180 mL) was slowly added to the reaction mixture, and then the mixture was stirred for 5 hours at 0C to 5C. The reaction mixture was filtered, and then dried under reduced pressure at 45C to 50C to obtain the title compound.Yield: 80%, 1172623-99-2

The synthetic route of 1172623-99-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SUN PHARMACEUTICAL INDUSTRIES LIMITED; PANDYA, Bhargav; THAKUR, Mandeep; SURADKAR, Swapnil; ANGADI, Surender; (42 pag.)WO2017/81590; (2017); 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.1197-66-6,2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one,as a common compound, the synthetic route is as follows.

A. 2,2,6,6-Tetramethyl-tetrahydro-2H-pyran-4-ol, 10a (0297) (0298) A solution of 2,2,6,6-tetramethyloxan-4-one (190 mg, 1.22 mmol) and NaBH4 (93 mg, 2.5 mmol) in THF (4 mL) and methanol (2 mL) was stirred for 1 h at RT. The reaction was then quenched by the addition of 0.1 mL of water. The resulting mixture was concentrated. The residue obtained was purified by column chromatography on silica gel (EtOAc/petroleum ether (1:5-1:3 v/v)) to give the compound 10a. 1H-NMR (300 MHz, CDCl3) delta (ppm): 3.88-3.97 (m, 1H), 1.71-1.77 (m, 2H), 1.36-1.37 (m, 1H), 1.20-1.25 (m, 1H), 0.97-1.05 (m, 6H), 0.89-0.95 (m, 6H)., 1197-66-6

As the paragraph descriping shows that 1197-66-6 is playing an increasingly important role.

Reference£º
Patent; Janssen Pharmaceutica NV; Meegalla, Sanath; Huang, Hui; Player, Mark R.; (53 pag.)US2016/9662; (2016); 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.127956-11-0,Methyl 4-oxotetrahydro-2H-pyran-3-carboxylate,as a common compound, the synthetic route is as follows.

To a suspension ofguanidine hydrochloride (906 mg, 9.48 mmol) in ethanol (30 mL) was added sodium ethoxide (4.03 mL, 9.48 mmol) and the resulting mixture was stirred at room temperature for 10 mm before addition of methyl 4-oxotetrahydro-2H-pyran-3- carboxylate (1 .00 g, 6.32 mmol) in ethanol (35 mL). The reaction mixture was heatedat 80 00 overnight then concentrated to dryness, the residue was diluted with water and the pH was adjusted to 4 with HCI (iN, aq.). The resulting mixture was stirred at room temperature for 2 hours. The precipitated solids were isolated by filtration, washed with water and dried in vacuo to give the titled compound as a light yellow solid (860 mg, 81%).1H NMR (400 MHz, DMSO-d6) 6 ppm 2.36 (t, J = 5.56 Hz, 2 H),3.77 (t, J = 5.56 Hz, 2 H), 4.24 (s, 2 H), 6.34 (s, 2 H), 10.78 (s, 1 H)., 127956-11-0

As the paragraph descriping shows that 127956-11-0 is playing an increasingly important role.

Reference£º
Patent; JANSSEN SCIENCES IRELAND UC; JONCKERS, Tim, Hugo, Maria; RABOISSON, Pierre, Jean-Marie, Bernard; GUILLEMONT, Jerome, Emile, Georges; MC GOWAN, David, Craig; EMBRECHTS, Werner, Constant, Johan; COOYMANS, Ludwig, Paul; CALMUS, Laurent; (18 pag.)WO2018/2319; (2018); 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.141095-78-5,2-Bromo-1-(tetrahydro-2H-pyran-4-yl)ethanone,as a common compound, the synthetic route is as follows.

General procedure: Caution alpha-Azido ketones are potentially explosive compounds and should be handled with care. A mixture of alpha-bromo ketone 1a-g (1 equiv) and sodium azide (1.1-1.2 equiv) in MeOH or Me2CO (2.5 ml/mmol) was stirred for 2-17 h and then the solvent was evaporated. The residue was partitioned between water and EtOAc, the organic layer was washed with water, brine, dried over Na2SO4,and evaporated. alpha-Azido ketones 2d,15 2e,16 and 2f17 have been previously reported in literature. alpha-Azido ketones 2a-c, g do not ionize under ESI LCMS mode conditions and are too unstable to obtain elemental analysis., 141095-78-5

141095-78-5 2-Bromo-1-(tetrahydro-2H-pyran-4-yl)ethanone 13197225, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Bobi?eva, Olga; Lo?a, Ein?rs; Chemistry of Heterocyclic Compounds; vol. 54; 11; (2018); p. 1070 – 1074; Khim. Geterotsikl. Soedin.; vol. 54; 11; (2018); p. 1070 – 1074,5;,
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.2081-44-9,Tetrahydro-2H-pyran-4-ol,as a common compound, the synthetic route is as follows.

General procedure: In the following Reaction Scheme A-2 Butyl 4-hydroxypiperidine-1-carboxylate (1 eq.) Or tetrahydro-2H-p yr-4-ol (1 eq.),Methanesulfonyl chloride (MsCl, 1 eq.),Triethylamine (Et3N, 1 eq.) And 4-dimethylaminopyridine (DMAP, 0.4 eq.) Were dissolved in dichloromethane at 0 C and stirred at room temperature for 12 hours.Water was added to the reaction solution at 0 C and extracted three times with dichloromethane.The combined organic solvent layers were dried with magnesium sulfate and concentrated.This was purified by column chromatography to obtain a compound substituted with methanesulfonate.Subsequently, 4-iodo-1H-pyrazole (1 eq.) Was dissolved in DMF, cooled to 0 C, 60% sodium hydride (NaH, 1.2 eq.) Was added to the solution and the mixture was stirred at room temperature for 1 hour.The previously obtained compound (1.1 eq) was added to the reaction solution, and the mixture was heated and stirred at 100 C.Water was added to the reaction solution at 0 C, extracted three times with ethyl acetate, and the combined organic solvent layer was dried over magnesium sulfate.The obtained organic solvent layer was concentrated and purified by column chromatography to obtain an intermediate.

2081-44-9, The synthetic route of 2081-44-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Institute for Basic Science; KAIST; Hong Seung-u; Ma Sin-mi; Hong Sun-seon; Jeong Hoe-yun; (71 pag.)KR2019/23557; (2019); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics