Heterocyclic Building Blocks-Tetrahydropyrans

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 suspension of aluminum chloride (205.85 g, 1.54 mol) in dichloromethane (500 mL) was added a solution of glutaric anhydride (80 g, 0.7 mol) in dichloromethane (125 mL) at 0 C. The reaction mixture was stirred for 30 minutes. Fluorobenzene (67.36 g, 0.7 mol) was then added slowly. The progress of the reaction was monitored by TLC. Upon completion, the reaction mixture was poured into ice water (2000 mL) to precipitate a crude solid product, which was collected by filtration. The crude was re-dissolved in a 3% aqueous sodium hydroxide solution (1100 mL). After being washed with dichloromethane (300 mL), the aqueous solution was acidified to obtain a solid product. The product was filtered, washed with water, and vacuum dried to yield compound 3 (125 g). H NMR of compound 3 (CDCl3, 300M Hz): delta=2.10 (q, J=7.2 Hz, 2H), 2.51 (t, J=7.2 Hz, 2H), 3.65 (t, J=7.2 Hz, 2H), 7.13 (t, J=7.4 Hz, 2H), 7.98 (q, J=5.4 Hz, 2H)

108-55-4, 108-55-4 Dihydro-2H-pyran-2,6(3H)-dione 7940, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Heading (Nanjing) Pharmaceutical Technologies Co., Ltd.; Li, Wensen; Liu, Laiyue; Tang, Aichen; Wang, Yanmin; Wang, Hailong; Yu, Wansong; US2015/18565; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

10521-08-1, 2H-Pyran-2,4,6(3H,5H)-trione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a flask containing 50 g (0.39 mol) of acetonedicarboxylic acid anhydride was added 160 ml of cold dry MeOH. The monomethylester solution was allowed to stand for 1 h and filtered.. The filtrate of acetonedicarboxylic acid monomethyl ester was used directly in the following condensation reaction.

10521-08-1, 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

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,951127-25-6

At room temperature, 32e (0.338 g, 0.88 mmol) was dissolved in N, N-dimethylacetamide (6 mL) at room temperature, Intermediate 1 (0.317 g, 0.97 mmol) was added and the mixture was stirred at room temperature for 60 minutes. A solution of sodium tris(acetoxy)borohydride (0.371 g, 1.76 mmol) was added to the reaction solution at 0 C, and the mixture was gradually added to the reaction at room temperature for 3 hours. The reaction solution was cooled to 0 C, adjusted to pH 8 with water (20 mL) and aqueous ammonia (10 mL), extracted with dichloromethane (50 mL x 3). The organic phases were combined and washed with saturated brine solution (50 mL x 1) Dried over anhydrous magnesium sulfate, filtered, the filtrate was spin dried, and the column chromatography (dichloromethane / methanol (v / v) = 40: 1)A yellow solid 32f (0.292 g, yield 61%) was obtained.

951127-25-6 tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate 44193925, aTetrahydropyrans compound, is more and more widely used in various fields.

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

40191-32-0, Tetrahydro-2H-pyran-4-carbonyl chloride is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 3: ((S)-3-Hydroxy-pyrrolidin-1 -yl)-(tetrahydro-pyran-4-yl)-methanone The (S)-pyrrolidin-3-ol hydrochloride (3.69g, 29.9 mmol) and triethylamine (6.65 g, 9.16 mL, 65.7 mmol) were put in CH2CI2 (15 mL). The suspension was cooled at ~3C. To this mixture, a solution of tetrahydro-pyran-4-carbonyl chloride (4.67g, 29.9 mmol) in CH2CI2 (15 mL) was added slowly. Then the resulting reaction mixture was stirred for 1.5h at 3-10C. The reaction mixture was then concentrated to give a powder. To this powder, addition of EtOAc (100 mL). The solid was filtered and washed with EtOAc. The recovered filtrate was then concentrated to give ((S)-3-hydroxy-pyrrolidin-1-yl)-(tetrahydro-pyran-4-yl)-methanone as beige powder. (6.77 g, 98% yield). 1 H-NMR (400 MHz, Methanol-d4, 298 K): delta ppm 1.59-2.15 (m, 6H) 2.69-2.86 (m, 1 H) 3.43-3.75 (m, 6H) 3.94-4.00 (m, 2H) 4.37-4.48 (m, 1 H). LCMS: [M+H]+= 199.9, Rt(6)= 0.86 min

40191-32-0, 40191-32-0 Tetrahydro-2H-pyran-4-carbonyl chloride 2795505, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; NOVARTIS AG; FERNANDES GOMES DOS SANTOS, Paulo Antonio; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; SOLDERMANN, Nicolas; STOWASSER, Frank; TUFILLI, Nicola; ZECRI, Frederic; WO2013/1445; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

25850-22-0, 2,2-Dimethyltetrahydro-2H-pyran-4-amine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The 4-chloro-3-nitroquinoline-6-carbonitrile (4.74 g, 17.55 mmol) was suspended in MeCN (50 mL) then 2,2-dimethyltetrahydro-2H-pyran-4-amine (2.49 g, 19.3 mmol) was added, after the DIEA (4.54 g, 35.1 mmol) was added the mixture was stirred at 20C for 2h, turning brown to tan. LCMS indicated complete conversion to the desired product. The mixture was concentrated under vacuum, the residue was purified by silica gel column chromatography (PE/EtOAc = 1/1) to give the desired product (4.88 g, 85% yield) as yellow solid. The purity and structure of the product were confirmed by LCMS and 1HNMR. LCMS: RT 0.73 mm, MS 327.0) 1H NMR (400 MHz, DMSO-d6) O 9.09 (5,1H), 9.02 (5, 1H), 8.42 (d, J= 8.4 Hz, 1H), 8.15(dd, J= 8.6, 1.6 Hz, 1H), 8.01 (d, J= 8.6Hz, 1H), 3.98 (m, 1H), 3.76-3.66 (m, 1H), 3.60 (td, J = 12.2, 2.3 Hz, 1H), 2.01 (ddd, J =12.6, 4.6, 2.6 Hz, 1H), 1.93-1.82 (m, 1H), 1.67 (m, 1H), 1.56 (t, J = 12.3 Hz, 1H), 1.19(d, J = 7.7 Hz, 6H)., 25850-22-0

25850-22-0 2,2-Dimethyltetrahydro-2H-pyran-4-amine 3809203, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; PFIZER INC.; CHAPPIE, Thomas Allen; GALATSIS, Paul; GARNSEY, Michelle Renee; HELAL, Christopher John; HENDERSON, Jaclyn Louise; KORMOS, Bethany Lyn; KURUMBAIL, Ravi G.; MARTINEZ-ALSINA, Luis Angel; PETTERSSON, Martin Youngjin; STEPAN, Antonia Friederike; WAGER, Travis T.; (149 pag.)WO2018/163030; (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.101691-65-0,(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

Step B: 1-(Tetrahydropyran-4-yl)methyl-7-chloro-1H-indole-3-carboxylic acid To a solution of 7-chloro-1H-indole-3-carboxylic acid (7.5 g, 38.0 mmol) in dimethylformamide (100 ml) at 10 C. under nitrogen was added sodium hydride (60% dispersion in mineral oil, 3.1 g, 76.0 mmol) portionwise over 10 mins, maintaining the temperature below 15 C. The cooling bath was removed and the suspension stirred for 90 mins. Toluene-4-sulfonic acid tetrahydopyran-4-ylmethylester (14.6 g, 53.0 mmol) was added. The mixture was heated at 50 C. with stirring for 6 h. Dimethylformamide was removed by evaporation and the residue was dissolved in water (500 ml). The emulsion was washed with dichloromethane (2*100 ml). The aqueous phase was acidified to pH 1 using 5 M hydrochloric acid and the precipitate filtered off, washed with water to neutrality and dried to afford 1-(tetrahydropyran-4-yl)methyl-7-chloro-1H-indole-3-carboxylic acid (15.0 g, 51.0 mmol) as a white solid., 101691-65-0

The synthetic route of 101691-65-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AKZO NOBLE N.V.; US2007/82931; (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.110238-91-0,Methyl tetrahydro-2H-pyran-4-carboxylate,as a common compound, the synthetic route is as follows.

To 250 mL of LiAIH4 (2.3 M solution in THF, 0.58 mol) in THF (200 mL) is added dropwise a solution of 130 mL (0.974 mol) of tetrahydro-pyran-4-carboxylic acid methyl ester in THF (900 mL) under nitrogen atmosphere. The temperature is kept at 40-45 C with an ice-bath. Upon complete addition, the reaction is stirred at RT for 1 .5 h. The reaction is cooled in an ice-bath and quenched with addition of water (22 mL), 15% aq. NaOH solution (21 mL) and water (66 mL). The resulting precipitate is removed by filtration through Celite and is rinsed with THF (300 mL). The filtrate is concentrated under reduced pressure to afford 102.5 g of (tetrahydro- pyran-4-yl)-methanol. Yield: 91 %, 110238-91-0

110238-91-0 Methyl tetrahydro-2H-pyran-4-carboxylate 2773520, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; BINDER, Florian; DOODS, Henri; MUELLER, Stephan, Georg; NICHOLSON, Janet, Rachel; SAUER, Achim; WO2014/184327; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

23462-75-1, Dihydro-2H-pyran-3(4H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 23: 3-methyl-8-(tetrahydro-2H-pyran-3-vn-4-((4-r3-(trifluoromethyl)phenvnpiperazin-1-yl)carbonyl)-1-oxa-8-azaspiror4.51dec-3-en-2-one Triethylamine (0.08 mL, 0.65 mmol) and dihydro-pyran-3-one (108 mg 1.08 mmol) were added into a solution of 3-methyl-4-({4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}carbonyl)-1-oxa-8- azaspiro[4.5]dec-3-en-2-one dihydrochloride (Example 1 , 100 mg, 0.20 mmol) in anhydrous dichloroethane (5 mL) cooled at 0C. Sodium triacetoxyborohydride (137 mg, 0.65 mmol) and trimethylorthoformate (120 mg, 1.08 mmol) were added and the resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with dichloromethane (20 mL) and washed with water (20 mL) and brine (20 mL). The organic layer was dried (MgS04) and concentrated under vacuum. After purification by flash chromatography (silica), the title compound was obtained as a white solid. 1H NMR (CDCI3, 400 MHz): delta 7.45-7.42 (m, 1 H), 7.24 (d, J = 9.0 Hz, 1 H), 7.20 (s, 1 H), 7.11 (d, J = 7.6 Hz, 1 H), 3.81-3.80 (m, 2H), 3.71-3.69 (m, 2H), 3.55 (s, 2H), 3.15 (s, 4H), 2.81-2.80 (m, 2H), 2.32-2.31 (m, 4H), 2.17 (s, 2H), 1.89-1.88 (m, 2H), 1 .75 (s, 3H), 1.69-1.61 (m, 2H), 1.48-1.38 (m, 3H). LCMS (Method D): Mass found (M+ 508.3), Rt (min): 3.88, Area (%): 93.6 (Max. Chrom.), 94.5 (254 nm). HPLC (Method A): Rt (min): 3.89, Area (%): 93.6 (Max. Chrom.), 94.4 (254 nm).

23462-75-1, The synthetic route of 23462-75-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARES TRADING S.A.; JORAND-LEBRUN, Catherine; SWINNEN, Dominique; GERBER, Patrick; KULKARNI, Santosh; WO2012/130915; (2012); A1;,
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

951127-25-6, At room temperature, 6a(0.327 g, 1.10 mmol) was dissolved in Nu, Nu-dimethylacetamide(4 mL) was added intermediate 1 (0.356 g, 1.10 mmol) and stirred at 0 C for 1 hour. Sodium tris (acetoxy) borohydride (0.303 g, 1.43 mmol) was added to the reaction solution and allowed to warm to room temperature for 16 hours. The reaction solution was cooled to C, followed by adding water and aqueous ammonia to adjust the pH to 8 to precipitate a white solid. The filter cake was washed successively with water (5 mL chi 3) and petroleum ether (10 mL chi 1). The residue was dried and the cake was dried to give a white solid 6b (0.367 g, 63.7% yield).

951127-25-6 tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate 44193925, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; SICHUAN HAISCO PHARMACEUTICAL CO., LTD; FAN, JIANG; FENG, JIAN-CHUAN; PENG, FEI; CHEN, QING-PING; (89 pag.)TW2017/8224; (2017); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1197-66-6, 2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Zinc powder (520mg, 8mmol) was added 20mL of tetrahydrofuran, was added titanium tetrachloride (0.44mL, 4mmol), the reaction was refluxed for 2 hours, cooled to 0 deg.] C, was added lithium tetrahydroaluminate (76mg, 2mmol), with stirring under ice 10 minutes, triethylamine (0.28 mL, 2 mmol) was added and the reaction was refluxed for 1 hour. Prefabricated 5 mL(4-bromophenyl) (1- (tetrahydro-2H-pyran-2-yl) -1H-indazol-5-yl) methanone1c (193mg, 0.5mmol) and 2,2,6,6-tetramethyl-dihydro -2H- pyran -4 (3H) – tetrahydrofuran-one (200mg, 1.28mmol), the reaction was refluxed for 1 hour. After completion of the reaction, the reaction was quenched with 10mL water and extracted with ethyl acetate (10mL ¡Á 3), the organic phase was concentrated under reduced pressure, purified by silica gel column chromatography with eluent systems resulting residue was purified B to give the title product5 – ((4-bromophenyl) (2,2,6,6-tetramethyldihydro-2H-pyran-4 (3H) -ylidene) methyl) -1- (tetrahydro-2H-pyran-2-yl) -1H-indazole10a (190 mg, white solid) in 74.5% yield.

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

Reference£º
Patent; Yang, Fanglong; Wang, Chunfei; Wang, Yang; He, Mingxun; Hu, Qiyue; He, Feng; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; (53 pag.)CN106518768; (2017); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics