Heterocyclic Building Blocks-Tetrahydropyrans

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

(3R,4R)-4-(6-Carbamoyl-5-(6-isopropoxypyridin-2-ylamino)pyridazin-3-ylamino)tetrahydro-2H-pyran-3-ylcarbamate [0524] [0525] To a solution of 6-chloro-4-(6-isopropoxypyridin-2-ylamino)pyridazine-3-carboxamide (270 mg, 877 mumol, Eq: 1.00) in NMP (3.51 mL) was added tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (190 mg, 877 mumol, Eq: 1.00) and the mixture heated to 140 C. Over the next 36 hrs three additional portions of amine were added at 12 h intervals. At 48 hrs the mixture was cooled, diluted with EtOAc, and washed with water and brine (2¡Á). The organic layer was concentrated onto silica and purified by chromatography (70% to 100% EtOAc/hexanes) to (3R,4R)-4-(6-carbamoyl-5-(6-isopropoxypyridin-2-ylamino)pyridazin-3-ylamino)tetrahydro-2H-pyran-3-ylcarbamate (190 mg, 44.4%). 1H NMR (400 MHz, CHLOROFORM-d6) delta ppm 11.37 (s, 1H), 8.06 (s, 1H), 7.92 (s, 1H), 7.49 (t, J=7.5 Hz, 1H), 6.44 (d, J=8.0 Hz, 1H), 6.31 (d, J=8.2 Hz, 1H), 5.91 (s, 1H), 5.67 (s, 1H), 5.38 (d, J=8.5 Hz, 1H), 5.15 (m, 1H), 4.30 (m, 1H), 4.05 (s, 1H), 4.00 (d, J=12.5 Hz, 1H), 3.90 (d, J=12.3 Hz, 1H), 3.68 (d, J=11.3 Hz, 1H), 3.61 (t, J=10.8 Hz, 1H), 2.27 (s, 1H), 1.79 (m, 1H), 1.44 (m, 15H).

1240390-36-6 tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate 68077633, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Hoffman-La Roche Inc.; Hermann, Johannes Cornelius; Kennedy-Smith, Joshua; Lucas, Matthew C.; Padilla, Fernando; Soth, Michael; US2013/178478; (2013); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

EXAMPLE IG 4- {4-[(4′-chloro- 1 , 1 ‘-biphenyl-2-yl)methyl]piperazin-l -yl} -N-( {3-nitro-4-[(tetrahydro-2H- pyran-4-ylmethyl)amino]phenyl}sulfonyl)-2-phenoxybenzamide; EXAMPLE IE (90 mg), EXAMPLE IF (45 mg), l-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (65 mg), and 4-dimethylaminopyridine (22 mg) were stirred in CH2Cl2 (4 mL) for 24 hours. The reaction was cooled and chromatographed on silica gel with 20- 100% ethyl acetate/hexanes. H NMR (300MHz, dimethylsulfoxide-d6) delta 11.55 (brs, IH), 8.63 (t, IH), 8.47 (d, IH), 7.75 (d, IH), 7.46 (m, 6H), 7.35 (m, 2H), 7.24 (m, 3H), 7.15 (d, IH), 6.99 (dd, IH), 6.82 (d, 2H), 6.75 (d, IH), 6.38 (d, IH), 3.86 (br d, 2H), 3.49 (m, 2H), 3.37 (br s, 2H), 3.15 (br s, 4H), 2.34 (br s, 4H), 1.91 (br s, 4H), 1.64 (br d, 2H), 1.29 (m, 3H).

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

Reference£º
Patent; ABBOTT LABORATORIES; BRUNCKO, Milan; DING, Hong; DOHERTY, George, A.; ELMORE, Steven, W.; HASVOLD, Lisa; HEXAMER, Laura; KUNZER, Aaron, R.; MANTEI, Robert, A.; MCCLELLAN, William, J.; PARK, Chang, H.; PARK, Cheol-min; PETROS, Andrew, M.; SONG, Xiaohong; SOUERS, Andrew, J.; SULLIVAN, Gerard, M.; TAO, Zhi-fu; WANG, Gary, T.; WANG, Le; WANG, Xilu; WENDT, Michael, D.; WO2010/65865; (2010); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5631-96-9,2-(2-Chloroethoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

A reaction vessel is charged with tert-butyl 3,6,8-trioxo-2-(4-(prop-2-yn-1-yloxy)phenyl)- 2,7-diazaspiro[4.5]decane-7-carboxylate (1 equiv.), potassium carbonate (2 equiv.) and DMF (0.5 M).2-(2-Chloroethoxy)tetrahydro-2H-pyran (1.1 equiv.) is added and the reaction is heated at 110 C for 12 hours. The reaction is then cooled to ambient temperature and concentrated. The residue is taken up in water and ethyl acetate and the layers separated. The aqueous layer is extracted with ethyl acetate (2x). The combined organic layer is washed with brine, dried over sodium sulfate, filtered and concentrated. The crude residue is used directly in the following reaction.

5631-96-9 2-(2-Chloroethoxy)tetrahydro-2H-pyran 254951, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; LAZARSKI, Kiel; MICHAEL, Ryan, E.; (771 pag.)WO2017/197036; (2017); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.108-55-4,Dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.

To a stirred suspension of aluminum chloride (205.85g, 1. 54MOL) in dichloromethane(500ML) was added a solution of glutaric anhydride (80g, 0. 7MOL) indichloromethane (125ML) at 0C. The reaction mass was stirred for30minutes and fluorobenzene (67.36g, 0. 7MOL) was added to the reactionmass slowly. The reaction was monitored for completion by TLC and thenpoured into ice cold water (2000ML) under stirring and the separatedsolids were collected by filtration. The solids were dissolved in 3%aqueous sodium hydroxide solution (1100ML) and washed withdichloromethane (300ML). The aqueous layer was acidified to give aprecipitate. The solids were filtered and washed with water andvacuum-dried to yield the title product (125g, yield: 85%). LHNMR(CDC13) 8 : 8.027-7. 98 (M, 2H), 7.17-7. 11 (M, 2H), 3.067 (t, 2H), 2.52(t, 2H), 2.14-2. 04 (M, 2H).

As the paragraph descriping shows that 108-55-4 is playing an increasingly important role.

Reference£º
Patent; RANBAXY LABORATORIES LIMITED; WO2004/99132; (2004); A2;,
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Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29943-42-8,Dihydro-2H-pyran-4(3H)-one,as a common compound, the synthetic route is as follows.

To a solution of 8a (5.Og, 50mmol) in THF (25mL) cooled to O0C, was added a suspension Of LiAlH4 (3.8g, O.lmol) in THF (5OmL) slowly. The resulting mixture was stirred at O0C for 30min, then was added water (3.8mL), followed by aqueous 15% NaOH (3.8mL) and water (1 1.4mL). The mixture was filtered and the solid was washed with ethyl ester (70mLchi2). The combined filtrate was evaporated to afford 8b (5.09g, 99%).

As the paragraph descriping shows that 29943-42-8 is playing an increasingly important role.

Reference£º
Patent; XCOVERY, INC.; WO2008/88881; (2008); 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.14774-37-9,Tetrahydropyran-4-methanol,as a common compound, the synthetic route is as follows.

To a solution of 57 (8.12g, 10mmol) and N-bromobutanimide (NBS) (13.71g, 248mmol) in 130 DCM (400mL) was added PPh3 (20.17g, 248mmol) at 0C. The reaction mixture was stirred at room temperature for 1-2h. The resulting mixture was washed with water (20mL) and brine (3¡Á20mL). The organic layer was concentrated and the residue was purified by silica gel flash chromatography (eluting with ethyl acetate in petroleum ether 2-5%) to give the product58 as a colorless oil (6.2g, yield=49%). 1H NMR (400MHz, CDCl3) delta 3.98 (dd, J=11.2Hz, 4.4Hz, 2H), 3.37 (td, J=12.0Hz, 1.6Hz, 2H), 3.28 (d, J=6.4Hz, 2H), 1.91-1.84 (m, 1H), 1.76 (d, J=13.2Hz, 2H), 1.35 (qd, J=12.4Hz, 4.4Hz, 2H); LC/MS (ESI, m/z) 179.01 [M+H]

The synthetic route of 14774-37-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wang, Beilei; Wu, Jiaxin; Wu, Yun; Chen, Cheng; Zou, Fengming; Wang, Aoli; Wu, Hong; Hu, Zhenquan; Jiang, Zongru; Liu, Qingwang; Wang, Wei; Zhang, Yicong; Liu, Feiyang; Zhao, Ming; Hu, Jie; Huang, Tao; Ge, Juan; Wang, Li; Ren, Tao; Wang, Yuxin; Liu, Jing; Liu, Qingsong; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 896 – 916;,
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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

Compound 26 (0.10 g, 0.18 mmol), Compound 3 (0.055 g, 0.18 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 0.052 g, 0.27 mmol) and 4-dimethylaminopyridine (DMAP, 0.044 mg, 0.36 mmol) were added to It was stirred at room temperature for 10 h in dichloromethane (20 ml). The reaction was quenched with water (10 mL). Dry over anhydrous sodium sulfate, remove the solvent, The concentrate was subjected to column separation (eluent: ethyl acetate/methanol (v/v) = 30:1), Obtained 90 mg of a yellow solid, The yield was 59%.

1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Liu Zhiqiang; (35 pag.)CN108658983; (2018); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

951127-25-6, tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

70 f (1.78 g, 3.2 mmol) was dissolved in N,N-dimethylacetamide (10 mL)Intermediate 1 (1.15 g, 3.52 mmol) was added and reacted at room temperature for 30 min.The reaction system was cooled to 0 C, Sodium borohydrophosphate (1.37 g, 6.24 mmol) was added, reacted for 30 minutes, The reaction was continued at room temperature for 2 hours. The reaction solution was cooled to 0 C, water (40 mL) was added in that order, aqueous ammonia (5 mL) was added to adjust the pH to 9, and the solid was washed with water (50 mL x 3). The solid was dissolved in dichloromethane, dichloromethane ), The organic phase was combined, washed with saturated brine solution (50 mL), dried over anhydrous sodium sulfate, filtered, the filtrate was concentrated, and purified by silica gel column chromatography (dichloromethane / methanol (v / v) = 20: 1) ,A 70 g (1.15 g, yield 85%) of a white solid was obtained.

The synthetic route of 951127-25-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sichuan Haisco Pharmaceutical Co.,Ltd.; FAN, JIANG; ZHANG, CHEN; PENG, FEI; WU, YE; FENG, JIANCHUAN; WANG, JIANMIN; ZHENG, SUXIN; WEI, YONGGANG; YE, FEI; (350 pag.)TW2017/8220; (2017); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

108-55-4, Dihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a suspension of 48.6 mmol of the proper phenyl derivative and 71.3 mmol of AlCl3 in 60 mL of dry DCM, cooled at 0C, a solution of 32.4 mmol of the proper anhydride in 30 mL of dry DCM was added. The reaction was stirred at rt for 12 h except for the synthesis of 10, which needed only 1 h to proceed to completion. The mixture was then quenched with water and concentrated sulfuric acid; the organic phase was separated from the aqueous one and the solvent evaporated under vacuum. The residue was dissolved in EtOAc, extracted with a 10% NaOH aqueous solution, then acidified with a 1N HCl aqueous solution and re-extracted with EtOAc. Finally the organic phase was dried over MgSO4, filtered and concentrated in vacuo to afford pure compounds 11-13. 5-(3,4-dimethoxyphenyl)-5-oxopentanoic acid (11) 92% yield. 1H NMR (300 MHz, CDCl3): delta = 7.51-7.54 (m, 1H), 7.47 (s, 1H), 6.82 (d, 1H, J = 9.1 Hz), 3.88 (s, 3H), 3.87 (s, 3H), 2.97 (t, 2H, J = 7.8 Hz), 2.44 (t, 2H, J = 7.8 Hz), 2.02 (m, 2H) ppm.

As the paragraph descriping shows that 108-55-4 is playing an increasingly important role.

Reference£º
Article; Guariento, Sara; Karawajczyk, Anna; Bull, James A.; Marchini, Gessica; Bielska, Martyna; Iwanowa, Xenia; Bruno, Olga; Fossa, Paola; Giordanetto, Fabrizio; Bioorganic and Medicinal Chemistry Letters; vol. 27; 1; (2017); p. 24 – 29;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

62071-40-3, 4-(Tetrahydropyran-4-yl)phenylamine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

29 mg of 6-chloro-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide (the compound of Example 20) and 35 mg of 4-(tetrahydro-2H-pyran-4-yl)aniline were dissolved in 0.35 mL of 1,4-dioxane, to which 8.0 mg of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane, 17 mg of 1,1′-bis (diphenylphosphino)ferrocene and 12 mg of sodium tert-butoxide were added, and stirred using a microwave reaction apparatus under an argon atmosphere at 100 C. for 1 hour. After cooling, the solvent was evaporated and the residue was purified by silica gel thin layer chromatography (chloroform:methanol=20:1) to obtain 7 mg (16%) of the title compound as a white crystalline powder.m.p. 228-237 C.1H-NMR (400 MHz, CDCl3) delta: 1.55-1.70 (4H, m), 3.35-3.46 (3H, m), 3.90-3.97 (2H, m), 4.42 (2H, d, J=5.8 Hz), 5.74 (1H, s), 7.00 (2H, d, J=6.4 Hz), 7.06 (2H, d, J=8.5 Hz), 7.15 (1H, t, J=9.5 Hz), 7.30 (2H, d, J=8.5 Hz), 8.37 (1H, s), 8.79 (1H, s), 9.05 (1H, t, J=5.6 Hz).

62071-40-3 4-(Tetrahydropyran-4-yl)phenylamine 20365472, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Kitamura, Takahiro; Yamada, Hajime; Takemura, Shunji; Ashikawa, Masanori; Ishikawa, Tetsuya; Miyake, Yoshiharu; Kouketsu, Akiyasu; Sato, Seiichi; Ishiwata, Hiroyuki; Tabunoki, Yuichiro; Shibasaki, Manabu; Ozawa, Takatoshi; Shigemi, Ryota; Doi, Takeshi; Tamura, Masahiro; US2011/237590; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics