Category: Tetrahydropyrans

1228779-96-1, 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1228779-96-1

General procedure: To a solution of appropriate crude acid (1 eq) in CH2Cl2 wereadded EDCI (3 eq), DMAP (0.3 eq) and DIPEA (3 eq). The solutionwas stirred at room temperature for 0.5 h and compound 23 [7] (0.8eq) was added. The resulting mixture was stirred for another 8 hand water was added. The layers were separated, and the aqueouslayer was extracted with CH2Cl2. The combined organic layer waswashed with brine, dried over anhydrous Na2SO4, filtered, andconcentrated under vacuo. The residue was prified by chromatography(CH2Cl2/CH3OH 40:1) to provide target compounds 27a-i,28a-d and 34a-c.

The synthetic route of 1228779-96-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Liu, Xiaohua; Zhang, Yu; Huang, Wenjing; Luo, Jia; Li, Yang; Tan, Wenfu; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 149 – 165;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1228779-96-1, 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1228779-96-1

To a solution of 2-(lH-pyrrolo[2,3-b]pyridine-5-yloxy)-4-(4-((2-4-chlorophenyl)-4,4- dimethylcyclohex-l-enyl)methyl)piperazin-l-yl)benzoic acid (100 g) in MDC (1500 ml) were added 3-nitro-4-((tetrahydro-2H-pyran-4yl)methylmaino)benzenesulfonamide (71.78 g),DMAP(6.4l g) and EDCI. HC1 (61.16 g) at room temperature and stirred till completion of reaction. After completion of reaction, water was added to the reaction mixture, stirred for 30 minutes and filtered at room temperature. The filtrate was stirred for 30 mins at room temperature and layers were separated. The organic layer (MDC) was distilled atmospherically below at 55 C to obtain residue (diamide content 5%). To residue methanol (1000 inL) was added and temperature was raised to 50-70C and solvent (100 mL) was distilled. To the reaction mass, sodium Hydroxide (10.50 g) solution in methanol was added at 55-60C and stirred for 2 hrs. Reaction mixture was cooled to 40-45C, stirred for 45 mins and filtered. Wet cake was washed with methanol (200 ml). Obtained compound was added to dimethylformamide (300 mL), heated at 50-60C and stirred for 30-50 mins to get clear solution. Methanol (300 mL) was added to the solution at 50-60C and stirred for 30-50 mins. Reaction mixture was cooled to 25- 35C and stirred for 8hrs.The reaction mixture was filtered and solid was washed with mixture of DML: Methanol (1 :3) (100 mL). Wet cake was dried at 25-35C for 1 hr in VTD to obtain sodium salt of Venetoclax (Form AL2 of Venetoclax) 80-90 g. (>53% yield) (diamide content > 0.3% ).1H NMR (300 MHz, Dimethyl sulfoxide d6) 11.53 (br s, 1H), 8.42(br s, 1H), 8.34(t, 1H), 7.95(d, 1H), 7.64(t, 2H), 7.27-7.4l(m, 4H), 6.62-6.78(dd, 2.02), 6.29-6.30(br s, 2H), 3.83-3.88(d, 2H), 3.42(br s, 4H), 3.l9-3.29(m, 6H), 3.0l(br s, 4H), 2.89(s, 1H), 2.74-2.72(m, 3H), 2.20(br s, 6 H), l.95-l.23(m, 9H), 0.92(s, 6H).13C NMR:-l70.89, 156.59, 153.06, 149.85, 146.21, 145.00, 142.54, 135.25, 134.99, 134.45, 133.52, 132.57, 131.26, 130.49, 129.66, 129.61, 128.51, 127.37, 125.48, 123.54, 120.02, 116.22, 113.97, 109.76, 106.55, 100.05, 67.13, 60.27, 52.80, 49.09, 48.31, 47.93, 46.78, 36.25, 35.32, 34.34, 31.24, 30.70, 29.33, 28.37.

The synthetic route of 1228779-96-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ALEMBIC PHARMACEUTICALS LIMITED; TVSK, Vittal; CHUDASAMA, Dinesh; DONTHUKURTHI, Saisuryanarayana; SHAH, Tejas; PATIL, Chetan; VELISOJU, Mahendar; SIRIPRAGADA, Mahender Rao; (28 pag.)WO2019/150253; (2019); 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.,1197-66-6

To a stirred suspension of zinc powder (0.54 g, 8.13 mmol) in THF (20 mL) was slowly added TIC) 4 (0.45 mL, 4.07 mmol) via syringe at room temperature under a nitrogen atmosphere. The mixture was heated at reflux for 2 h. A solution of (4- bromophenyl) (3-fluoro-4-hydroxyphenyl) methanone (82) (0.30 g, 1.02 mmol) and 2,2, 6, 6-tetramethyl tetrahydro-4H-pyran-4-one (0.49 g, 3.05 mmol) in THF (6 mL) was added to the mixture. The reaction mixture was heated at reflux with stirring under a nitrogen atmosphere for 1.5 h. The reaction mixture was allowed to cool to room temperature. To the reaction mixture was slowly added 10% aqueous K2CO3 (20 mL). The reaction mixture was filtered through a pad of Celite and the pad was washed with EtOAc (100 mL). The filtrate was transferred to a separatory funnel and the layers were separated. The aqueous layer was further extracted with EtOAc (25 mL). The combined organic phase was washed with brine, dried over NA2SO4, filtered, and the filtrate was concentrated to give the crude product as yellow oil. The crude product was purified by chromatography on a silica gel column eluted with a gradient from hexanes to 15% EtOAc: hexanes to give 0.40 g (94%) of compound 136 as a YELLOW FOAM. H NMR (400 MHz, CDCI3) : 8 1.20 (s, 6H), 1.22 (s, 6H), 2.18 (s, 2H), 2.23 (s, 2H), 5.04 (d, J = 4.0 Hz, 1 H), 6.80-6. 88 (m, 2H), 6.93 (t, J = 8.6 Hz, 1 H), 7.02 (d, J = 8.4 Hz, 2H), 7.42 (d, J = 8.3 Hz, 2H). LCMS (ES): m/z 417 (M-H)

The synthetic route of 1197-66-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/12220; (2005); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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;,
Tetrahydropyran – Wikipedia
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110238-91-0, Methyl tetrahydro-2H-pyran-4-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,110238-91-0

Production Example 2; Tetrahydro-2H-pyran-4-carboxamide; To methyl tetrahydro-2H-pyran-4-carboxylate (50 g, 347 mmol) was added concentrated ammonia water (50 mL), and the reaction mixture was stirred at room temperature for 43.5 hours. Thereafter, the reaction mixture was cooled in an ice water bath, and the precipitate was filtrated. Then, the precipitate was dried at 40¡ã C. under reduced pressure, to obtain 33.4 g of a title compound (yield: 74.6percent). 1H NMR (400 MHz, DMSO-d6) delta 1.45-1.62 (m, 4H), 2.28 (tt, J=11.1, 4.4 Hz, 1H) 3.26 (ddd, J=11.4, 11.4, 2.7 Hz, 2H), 3.82 (br d, J=11.4 Hz, 2H), 6.74 (br s, 1H), 7.21 (br s, 1H)

The synthetic route of 110238-91-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Negi, Shigeto; Shimizu, Toshikazu; Kuroda, Hiroshi; Shimomura, Naoyuki; Sasho, Manabu; Hoshino, Yorihisa; Kubota, Manabu; US2007/191613; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

110238-91-0, Methyl tetrahydro-2H-pyran-4-carboxylate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,110238-91-0

Ammonium hydroxide (1 L) was added to a solution of methyl tetrahydro-2//- pyran-4-carboxylate (20 tnL, 150 mmol) in methanol (500 mL), and the reaction was stirred overnight at ambient temperature. Additional ammonium hydroxide (500 mL) was added, and the reaction was stirred for four additional days. The methanol was removed under reduced pressure. Solid sodium chloride was added to the aqueous layer, which was extracted with chloroform (3 x 150 mL). The combined extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 1 1.4 g of tetrahydro- 2H-pyran-4-carboxamide as a white solid.

The synthetic route of 110238-91-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2007/75468; (2007); 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.10521-08-1,2H-Pyran-2,4,6(3H,5H)-trione,as a common compound, the synthetic route is as follows.,10521-08-1

To a 3 L flask with 53.6 g (0.41 mol) of 2,5-dimethoxydihydrofuran was added 1000 ml of 3N HCl solution.. The mixture was left to stand for 12 h at room temperature and then neutralized with ice-cold NaOH solution (equal moles) at 0 C. To this red solution, was added 41.3 g (0.62 mol) of methylamine hydrochloride in 300 ml H2O, the preformed methanol solution of the monomethylester (50 g (0.39 mol) of acetone dicarboxylic acid anhydride in 160 ml of methanol) and 50 g of sodium acetate in 200 ML of H2O. The mixture (PH 4.5) was stirred for 2 days and the acidity decreased to PH 4.9.. The red solution was extracted with hexane (450 ml*2) to remove nonpolar by-products.. The aqueous solution was basified first with NaOH (1N) to neutral PH, then with potassium carbonate.. sodium chloride (about 200 g) was added.. The saturated solution was extracted with CH2Cl2 (250 ml*8), then with a mixed solvent (t-butyl:1,2-dichloroethane, 37:63, 250 ml*8).. The CH2Cl2 extracted was dried over K2CO3 and solvent was removed to provide 19.6 g of a crude mixture which was separated by column chromatography (SiO2, 10% Et3N, 30-90% EtOAc in hexane and 10% methanol in EtOAc) to afford 7.5 g of 6(7)-methoxy-2-methoxycarbonyl-8-azabicyclo(3.2.1)octane-2-one as an oil and 7 g of 6(7)-hydroxy-2-methoxycarbonyl-8-azabicyclo-(3.2.1)octane-2-one as a crystalline solid.

The synthetic route of 10521-08-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Organix, Inc.; President and Fellows of Harvard College; US6353105; (2002); B1;,
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.101691-65-0,(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

EXAMPLE 85c; Preparation of intermediate 5-chloro-2-(tetrahydro-pyran-4-yl-methoxy)-benzaldehyde; A mixture of 5-chlorosalicylaldehyde (5.0 g, 32 mmol), toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester (8.6 g, 32 mmol) and K2CO3 (9.5 g, 68.8 mmol) in DMF (50 mL) was heated at 75 C. overnight. After cooled to room temperature, the mixture was poured into water. The aqueous phase was extracted with EtOAc twice. The combined organic phases were washed with water and brine, dried and concentrated. The residue was purified by column chromatography to give the title compound (7.0 g).

As the paragraph descriping shows that 101691-65-0 is playing an increasingly important role.

Reference£º
Patent; Chen, Li; Han, Xingchun; He, Yun; Yang, Song; Zhang, Zhuming; US2009/163512; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

185815-59-2, 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A 100 ml three-necked round-bottom flask, under nitrogen atmosphere, is added with 98% hydrazine hydrate (19.5 g, 0.382 mols), sodium hydroxide (12.4 g, 0.309 mol) in water (150 ml) and the solution is cooled to a temperature of -5C. 3-Isobutyl-glutaric anhydride (183.0 g, 1.075 mol) is dropped therein in about 1-2h, keeping the temperature below 0-5C and the mixture is reacted for about 1h. 35-37% Hydrochloric acid (450 ml) and toluene (400 ml) are added. Keeping a temperature of -5C, a solution of sodium nitrite (160.0 g, 2.026 mol) in water (320 ml) is added dropwise, keeping the temperature below 10-15C. After completion of the addition, the mixture is reacted for 15-20 minutes, afterwards the phases are separated and the aqueous phase is extracted with toluene (250 ml). The cooled combined organic phases are dropped into isopropanol (800 ml) under reflux in about 1 hour. The mixture is refluxed for about 30 minutes and the solution is concentrated to small volume. The resulting oil is taken up into hexane (500 ml) and left under strong stirring for 2-3 hours, the solid is filtered and dried at 50C for 16-18 hours. 205 g of a white solid are obtained, in a 78% yield. 1H-NMR (300 MHz, D2O, 28C): delta 7.00 (broad, 1H exchange with D2O); 4.70 (m, 1H); 3.00 (m, 1H); 2.80 (m, 1H); 2.10 (m, 2H); 1.95 (m, 1H); 1.60 (m, 1H); 1.20-1.00 (m, 8H); 0.80 (d, 6H).

185815-59-2 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione 11480690, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Dipharma Francis S.r.l.; EP2067768; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics