Downstream synthetic route of 624734-17-4

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

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, Intermediate 5a; Commercially available 3-Methoxy-tetrahydro-pyran-4-one (1 g, 7.68 mmol), commercially available (R)-(+)-l-phenylethylamine (0.99 ml, 7.68 mmol) and Raney-Nickel (200 mg) in 10 ml of dry ethanol were stirred under a hydrogen atmosphere (5 bar) for 15 days. The reaction mixture was diluted with 20 ml of methanol and 20 ml of tetrahydroiurane, stirred for 15 minutes, filtered on a celite pad and concentrated under vacuum. The crude product was loaded on a SCX cartridge (50g). The cartridge was washed with methanol and the desired product was eluted with a 7 M solution of ammonia in methanol. The basic organic phase was concentrated under vacuum and the crude product was purified by flash chromatography (dichloromethane/methanol= 98/2%) to obtain 710 mg (3.02 mmol) of the desired product as single stereoisomer (diastereoisomeric purity confirmed and relative cis stereochemistry assigned by NMR). GC/MS (method 3B) Rt = 35.04 min

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; EBEL, Heiner; FRATTINI, Sara; GIOVANNINI, Riccardo; HOENKE, Christoph; MAZZAFERRO, Rocco; SCHEUERER, Stefan; WO2011/141477; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 624734-17-4

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

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

Step H ((3aS,5S,6aR)-5-((3-methoxytetrahydro-2H-pyran-4-yl)amino)hexahydro-2H- cyclopenta[b]furan-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-l,6-naphthyridin-6(5H)- yl)methanone To a solution of the product of Step G (119 mg, 0.33 mmol, 1 eq) in DCM at rt was 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 sodium triacetoxyborohydride (355 mg, 1.67 mmol, 5 eq). After stirring overnight, saturated NaHC03 was added, the solution extracted with DCM, the organics combined, dried over MgS04, and concentrated. Purification by chromatography (12 g) eluting with 4 to 8% methanol DCM with ammonia afforded the title compound of Example 1. 1H NMR (CHLOROFORM-d) delta: 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). Calculated for C23H30F3N3O4: 470.2 (M+l); found: 470.2.

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

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; WINTERS, Michael P.; BRANUM, Shawn; FAWZY, Nagy E.; KANG, Fu-An; REUMAN, Michael; RUSSELL, Ronald K.; SUI, Zhihua; TELEHA, Christopher A.; WO2013/152269; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 624734-17-4

The synthetic route of 624734-17-4 has been constantly updated, and we look forward to future research findings.

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, To a solution of INTERMEDIATE 23 (1.79 g, 6.01 mmol), INTERMEDIATE 9 (2.35 g, 18.0 mmol), and triethylamine (0.838 mL, 6.01 mmol) in 30 mL of DCM was added sodium triacetoxyborohydride (5.10 g, 24.0 mmol) and the resulting mixture was stirred for three days. The reaction mixture was diluted with DCM and washed with saturated NaHC03 solution, then brine, dried over anhydrous MgS04, filtered, and concentrated to give 2.61 g of crude product, which was primarily a mixture of two isomers (assumed from related work to be the two cis tetrahydropyran isomers). INTERMEDIATE 24 could be used crude as a mixture of two isomers or could be purified and separated into two single isomers (see INTERMEDIATES 25A and 25B) and then carried on. ESI-MS calc. for C22H33NO4 : 375; Found: 376 (M+H).

The synthetic route of 624734-17-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK & CO., INC.; MERCK SHARP & DOHME LIMITED; WO2003/93231; (2003); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 624734-17-4

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

624734-17-4,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.624734-17-4,3-Methoxydihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

3-Methoxy-tetrahydro-pyran-4-one (1 g, 7.68 mmol), commercially available (R)-(+)-l- phenylethylamine (0.99 ml, 7.68 mmol) and Raney-Nickel (200 mg) in 10 ml of dry ethanol were stirred under a hydrogen atmosphere (5 bar) for 15 days. The reaction mixture was diluted with 20 ml of methanol and 20 ml of tetrahydrofurane, stirred for 15 minutes, filtered on a celite pad and concentrated under vacuum. The crude product was loaded on a SCX cartridge (50g). The cartridge was washed with methanol and the desired product was eluted with a 7 M solution of ammonia in methanol. The basic organic phase was concentrated under vacuum and the crude product was purified by flash chromatography(dichloromethane/methano 1= 98/2%) to obtain 710 mg (3.02 mmol) of the desired product as single stereoisomer (diastereoisomeric purity confirmed and relative cis configuration assigned by NMR).GC/MS (method 3B) Rt = 35.04 min

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; EBEL, Heiner; FRATTINI, Sara; GERLACH, Kai; GIOVANNINI, Riccardo; HOENKE, Christoph; SANTAGOSTINO, Marco; SCHEUERER, Stefan; TRIESELMANN, Thomas; WO2011/73155; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 624734-17-4

The synthetic route of 624734-17-4 has been constantly updated, and we look forward to future research findings.

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

A mixture of the product from Step B (99.8 mg, 0.156 mmol), 3-methoxydihydro-2H-pyran-4(JH)-one (60.91 mg, 0.468 mmol), 4A molecular sieves (0.2 g) and TEA (0.065 lmL, 0.468 mmol) in DCM (2 mL) was stirred at rt for 2 h, followed by addition of sodium triacetoxyborohydride (66.13 mg, 0.312 mmol). The resulting mixture was stirred at rt overnight. The reaction was quenched by addition of saturated NaHC03 aqueous solution, extracted with DCM, and dried over Na2S04. After removal of the solvent, the residue was purified by column chromatography (eluent: 5% 7N NH3 in methanol in DCM) to give the product as a yellowish gel. 1H-NMR (400 MHz, CDC13): delta 1.52 – 1.95 (m, 4H), 2.34 (br. s., 1 H), 2.61 – 2.89 (m, 6 H), 3.03 – 3.61 (m, 11 H), 3.63 – 4.13 (m, 7 H), 4.27 (br. s., 1 H), 4.57 – 5.11 (m, 2 H), 7.69 (br. s., 1 H), 8.71 (br. s., 1 H); LC/MS: C25H34F3N504: m/z 526.2 (M+H).

The synthetic route of 624734-17-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; CAI, Chaozhong; MCCOMSEY, David F.; SUI, Zhihua; KANG, Fu An; WO2014/14901; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Some tips on 624734-17-4

624734-17-4 3-Methoxydihydro-2H-pyran-4(3H)-one 23533610, 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.624734-17-4,3-Methoxydihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

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.

624734-17-4 3-Methoxydihydro-2H-pyran-4(3H)-one 23533610, aTetrahydropyrans compound, is more and more widely used in various.

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

Some tips on 624734-17-4

624734-17-4 3-Methoxydihydro-2H-pyran-4(3H)-one 23533610, 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.624734-17-4,3-Methoxydihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

A slurry of 3-methoxy-tetrahydro-pyran-4-one (0.4 g, 3 mmol-described in WO03/093266(A1)), ammonium formate (1.9 g, 30 mmol), 10% palladium on charcoal (Ig) in water:MeOH (1:5, 6 ml) was stirred overnight after which time it was filtered through Hyflo, the mixture concentrated to remove the MeOH, the residue taken up in Et2O, dried (Na2SO4) and concentrated to afford the title product (0.2 g, 49%) as a yellow oil (contaminated by 10-20% of the trans isomer). 1H NMR (300 MHz, CDCl3) (cis isomer) delta 1.60-1.80 (2H, m), 2.95-3.00 (1H, m), 3.22-3.43 (5H, m). 3.82-3.95 (1H, m), 4.01-4.13 (1H, m).

624734-17-4 3-Methoxydihydro-2H-pyran-4(3H)-one 23533610, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Aebi, Johannes; Binggeli, Alfred; Green, Luke; Hartmann, Guido; Maerki, Hans P.; Mattei, Patrizio; Ricklin, Fabienne; Roche, Olivier; US2009/29963; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 624734-17-4

624734-17-4 3-Methoxydihydro-2H-pyran-4(3H)-one 23533610, aTetrahydropyrans compound, is more and more widely used in various.

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

Intermediate 46b3-Methoxy-tetrahydro-pyran-4-one (1 g, 7.68 mmol), (R)-(+)-l-phenylethylamine (0.99 ml, 7.68 mmol) and Raney-Nickel (200 mg) in 10 ml dry ethanol were stirred under a hydrogen atmosphere (5 bar) for 15 days. The reaction mixture was diluted with 20 ml of methanol and 20 ml of tetrahydrofurane, stirred for 15 minutes, filtered on a celite pad and concentrated under vacuum. The crude product was loaded on a SCX cartridge (5Og). The cartridge was washed with methanol and the desired product was eluted with a 7 M solution of ammonia in methanol. The basic organic phase was concentrated under vacuum and the crude product obtained was purified by flash chromatography (dichloromethane/methanol= 98/2%) to obtain 710 mg (3.02 mmol) of the desired product as single stereoisomer (diastereoisomeric purity confirmed and relative cis stereochemistry assigned by NMR).

624734-17-4 3-Methoxydihydro-2H-pyran-4(3H)-one 23533610, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; EBEL, Heiner; FRATTINI, Sara; GIOVANNINI, Riccardo; HOENKE, Christoph; TRIESELMANN, Thomas; TIELMANN, Patrick; SCHEUERER, Stefan; HOBBIE, Silke (Marie Katrin); WO2010/70032; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics