Category: 1768-64-5

Brief introduction of 1768-64-5

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

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

Example 8 Preparation of ethyl 1-(4-tetrahydropyranyl)eth-1-ene-2 -carboxylate 9.6 g (400 mmol) of magnesium turnings are covered with tetrahydrofuran, about 2 ml of bromomethane are added, and the mixture is warmed to reflux. 38.45 g (300 mmol) of 4-chlorotetrahydropyran, dissolved in 100 ml of tetrahydrofuran, are added dropwise. The mixture is subsequently stirred for a further 30 minutes and cooled to 10 C., 42.9 g (300 mmol) of ethyl 1-(dimethylamino)eth-1-ene-2-carboxylate are added dropwise, and the mixture is stirred for a further 12 hours. Customary work-up gives 31.4 g (60%) of ethyl 1-(4-tetrahydropyranyl)eth-1-ene-2-carboxylate of boiling point 120 to 140 C./10 mmHg.

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

Reference£º
Patent; BASF Aktiengesellschaft; US5221753; (1993); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 1768-64-5

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

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

To a suspension of Mg (1.37 g, 56.5 mmol) and I2(10 mg) in THF (2 mL) was added a solution of 4-chlorotetrahydro-2H-pyran (2.72 g, 22.6 mmol) in THF (8 mL) at 60C drop wise. The mixture was stirred at 60C for 2 h. The mixture was diluted with THF (10 mL) and used directly. The Grignard reagent was added to a solution of G-6 (0.55 g, 1.28 mmol) in THF (5 mL) at 0C. The mixture was stirred at 0C for 1 h and treated with NH4C1 (10 mL, sat. aq.). The mixture was extracted with EtOAc (3 x 20 mL). The organic layer was separated, concentrated in vacuum, purified by silica gel column (PE/EtOAc=20/l to 5/1) to give a crude product, which was re-crystallized from CH3CN (10 mL) to give Compound 9 (180 mg, 27%) as a solid.1H NMR (400 MHz, CDC13) delta 4.05-3.97 (m, 2H), 3.41-3.25 (m, 3H), 2.10-1.91 (m, 3H), 1.88- 1.57 (m, 7H), 1.55-1.33 (m, 11H), 1.33-0.96 (m, 12H), 0.96-0.86 (m, 4H), 0.85 (s, 3H), 0.72- 0.63 (m, 4H).HPLC Rt = 4.73 min in 8.0 min chromatography, 50-100 AB.MS ESI calcd. for C30H48F3O2[M+H-H20]+497, found 497., 1768-64-5

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

Reference£º
Patent; SAGE THERAPEUTICS, INC.; SALITURO, Francesco G.; ROBICHAUD, Albert J.; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd L.; GRIFFIN, Andrew; LA, Daniel; (387 pag.)WO2018/75699; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Analyzing the synthesis route of 1768-64-5

1768-64-5, As the paragraph descriping shows that 1768-64-5 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.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.

4- (Pheyiylmethyl) morpholin-2-ylj (tetrahydro-2H-pyran-4-yl) methanone (8b); An inerted 6L reactor is charged with THF (242.5 mL), magnesium (54.47 g, 2240mmol) and 5% of the total amount of 4-chlorotetrahydropyran (12.28 mL, 112 mmol). Then, a small amount of methyl iodide (0.5 mL) and one iodine crystal is added. The reaction mixture is stirred and heated up to 64-66C. After initiation, the remaining 4- chlorotetrahydropyran (233.22 mL, 2127 mmol) diluted in THF (890 mL) is slowly added over 135 mins. The mixture is heated up for 30 additional minutes before being cooled to 0C. Then, the Weinreb amide 2b (370 g, 1400 mmol) diluted in THF (2777 mL) is added over 180 mins between 0-4C and the mixture is stirred for a further 60 mins. Then, acetic acid (48 mL, 0.83 mmol) is added to the mixture followed by a 55/45 : v/v : saturated NH4Cl/Ha0 mixture (2590 mL) keeping the temperature below 9C. The organic layer is washed with a 60/40: v/v: saturated NH4CI/H20 mixture (500 mL) and, after separation, toluene (1800 mL) and water (1800 mL) is added to the organic solution. Then after extraction, water (1100 mL) is added to the toluene mixture which is basified with 3.68 M Na2CO3aq (148 mL). The organic layer is dried over MgS04, filtered and concentrated under reduced pressure to dryness to yield compound 8b as the free base (400. 8 g, 98. 6% yield).

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

Reference£º
Patent; ELI LILLY AND COMPANY; WO2005/47272; (2005); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 1768-64-5

1768-64-5 4-Chlorotetrahydropyran 137202, aTetrahydropyrans compound, is more and more widely used in various.

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

70 mg (1.76mmol, l . leq.) of NaH was added into the solution of 455 mg (1.4mmol, leq.) 2 in DMF, and stirred for 1 hr at rt. 211mg (1.76mmol, l .leq.) of 4-chloro-2H-tetrahydropyran was then added and stirred overnight. After the reaction was complete, water was added, and then all the solvent was removed by filtration and the product was purified by column chromatography to obtain 942 mg of 3, with a yield of 60%., 1768-64-5

1768-64-5 4-Chlorotetrahydropyran 137202, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; ZHEJIANG BETA PHARMA INC.; KANG, Xinshan; LONG, Wei; MA, Cunbo; WANG, Yanping; SHEN, Xiaoyan; HU, Yunyan; TAN, Fenlai; WANG, Yinxiang; WO2012/62210; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Some tips on 1768-64-5

The synthetic route of 1768-64-5 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.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.

440 mg (12.7 mmol, 1.1 eq.) of NaH was added into the solution of 2 g (11.5 mmol, 1 eq.) 2-chloro-5-nitrophenol in DMF, and stirred for 1 hr at rt. And then, 1.5 g (12.7 mmol, 1.1 eq) of 4-chloro-2H-tetrahydropyran was added and stirred overnight. After the reaction was complete, water was added and filtered to remove solvent. The product was purified by column chromatography to obtain 1.7 g of 1, with a yield of 70%.

The synthetic route of 1768-64-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Zhejiang Beta Pharma Incorporation; Fujian Haixi Pharmaceuticals, Inc.; Kang, Xinshan; Long, Wei; Ma, Cunbo; Wang, Yanping; Shen, Xiaoyan; Hu, Yunyan; Tan, Fenlai; Wang, Yinxiang; US2013/225587; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 1768-64-5

The synthetic route of 1768-64-5 has been constantly updated, and we look forward to future research findings.

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

[00314] (Tetrahydro-2H-pyran-4-yl)magnesium chloride^o^ . To a vigorously stirred suspension of Mg (0.500 g, 20.57 mmol) turnings and iodine (0.019 g, 0.075 mmol) in THF (5 mL) under N2 (g) was added 1,2-dibromoethane (0.10 mL, 1.160 mmol) and 10% of a solution of 4-chlorotetrahydro-2H-pyran (1.00 mL, 9.24 mmol) in THF (5 mL). The mixture was heated to 60 C and as the reaction mixture turned clear and Grignard initiation took place, the remainder of the solution of 4-chlorotetrahydro-2H-pyran (1.00 mL, 9.24 mmol) in THF was added slowly over 30 min. The reaction mixture was stirred at 65 C for 2 h to deliver a solution of (tetrahydro-2H-pyran-4-yl)magnesium chloride in THF. The Grignard solution was used without any further purification.

The synthetic route of 1768-64-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian K.; AUDIA, James Edmund; COTE, Alexandre; GEHLING, Victor S.; HARMANGE, Jean-christophe; HEWITT, Michael C.; LEBLANC, Yves; NAVESCHUK, Christopher G.; TAYLOR, Alexander M.; VASWANI, Rishi G.; WO2012/75383; (2012); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Some tips on 1768-64-5

The synthetic route of 1768-64-5 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.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.

A solution of 4-chlorotetrahydro-2H-pyran (1.2 g, 10 mmol) in THF (5 mL) was added dropwise to a mixture of Mg (486 mg, 20 mmol) and I2 (1 mg) at 70oC. The mixture was stirred at 50oC for 0.5 h, diluted with THF (5 mL) and used directly. To a solution of (tetrahydro-2H- pyran-4-yl)magnesium chloride (4.14 mL, 1 M in THF) was added N-8-7_1 (500 mg, 1.38 mmol) in THF (5 mL) at 0C under N2. Then the mixture was stirred at 15oC for another 18 hrs. The reaction mixture was quenched with sat. NH4Cl (5 mL), and the resulting mixture was extracted with EtOAc (2 x 10 mL). The combined organic layer was washed with brine (5 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash column (0-15% EtOAc in PE) to give N-8-17_1 (350 mg, 57%) as a solid. 1H NMR (400 MHz, CDCl3) delta 4.08-3.91 (m, 2H), 3.43-3.31 (m, 2H), 3.31-3.25 (m, 1H), 1.98- 1.91 (m, 2H), 1.91-1.80 (m, 1H),1.70-1.50 (m, 10H), 1.50-1.41 (m, 2H), 1.41-1.32 (m, 5H), 1.32-1.15 (m, 9H), 1.15-0.92 (m, 6H), 0.92-0.83 (m, 7H), 0.65 (s, 3H) .

The synthetic route of 1768-64-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SAGE THERAPEUTICS, INC.; SALITURO, Francesco, G.; ROBICHAUD, Albert, J.; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd, L.; GRIFFIN, Andrew; LA, Daniel; (299 pag.)WO2018/75698; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 1768-64-5

The synthetic route of 1768-64-5 has been constantly updated, and we look forward to future research findings.

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

STEP A: Preparation of (2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-(tetrahydro-pyran-4-yl)-methanol To a suspension of magnesium in THF was added iodine followed by 4-chlorotetrahydropyran in THF at 65 C. Small amount of methylmagnesium bromide (3 drops) was added to initiate the reaction. The mixture was stirred at 65 C. for 1.5 hours, cooled to room temperature. 2-{[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-benzaldehyde in THF was treated with trimethylsilyl chloride and stirred at room temperature for 1 hour. The Grignard was then added to the aldehyde in THF at 0 C. via syringe. The mixture was stirred at 0 C. for 1.5 hours, quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. Combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by chromatography over 25+S Biotage silica column (eluted with 0-50% ethyl acetate in hexanes) to afford the title compound as a pale yellow foam (91.6 mg, 52%). 1H NMR (400 MHz, CDCl3) delta ppm 1.07 (d, J=13.28 Hz, 1H) 1.27-1.37 (m, 1H) 1.40-1.52 (m, 1H) 1.77-1.89 (m, 2H) 2.51 (s, 1H) 3.19-3.34 (m, 2H) 3.86 (dd, J=11.14, 3.53 Hz, 1H) 3.99 (dd, J=11.62, 3.73 Hz, 1H) 4.18 (s, 3H) 4.68-4.83 (m, 4H) 4.88 (d, J=15.35 Hz, 1H) 7.34 (s, 1H) 7.55 (s, 2H) 7.64 (s, 2H) 7.77 (s, 1H). MS (ES+) Calc: 597.2, Found: 598.4 (M+1). The racemic alcohol mixture was separated by chiral chromatography using preparative HPLC (Column: Chiralcel OJ; Dimension: 5 cm*50 cm; Mobile phase: 95/5 heptane/ethanol with 0.1% DEA, Flow rate: 120 mL/minutes). The expected preparative retention times for the two enantiomers are 26 minutes (Enantiomer 1) and 36 minutes (Enantiomer 2). Enantiomer 1: MS Calc: 597.2, Found: 598.4; 100% ee. Enantiomer 2: MS Calc: 597.2, Found: 598.4; 100% ee

The synthetic route of 1768-64-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Pfizer Inc; US2007/213371; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics