Heterocyclic Building Blocks-Tetrahydropyrans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1194-16-7,2,2-Dimethyltetrahydropyran-4-one,as a common compound, the synthetic route is as follows.

To a stirred solution of 2,2-dimethyltetrahydro-4H-pyran-4-one (2 g, 20 mmol) in MeOH (40 mL) and H2O (5 mL) was added ammonium formate (10.33 g, 160 mmol) and pallidum on carbon (0.5 g). The reaction was stirred under atmospheric hydrogen atmosphere for 5 h. The reaction mixture was filtered through bed of celite and washed with methanol. The resulting filtrate was concentrated under reduced pressure to afford 2,2-dimethyltetrahydro-2H-pyran-4-amine (2.5 g, 85%) as a colourless gummy material. (1S,4S)-4-((2-((2,2-Dimethyltetrahydro-2H-pyran-4-ylamino)-5-nitropyrimidin-4-yl)amino)cyclohexane-1-carboxamide.

1194-16-7, As the paragraph descriping shows that 1194-16-7 is playing an increasingly important role.

Reference£º
Patent; Celgene Corporation; CANAN, Stacie S.; HAWRYLUK, Natalie Anne; WITTY, Michael John; (74 pag.)US2017/348315; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

103260-44-2, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of sodium hydroxide (15.9 g, 44.06 mmol) in water (150 ml) was added dropwise to a solution of ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (15 g, 8.81 mmol) in methanol (150 ml) at a temperature of 0 ¡ãC or below, and the mixture was stirred at room temperature for 15 hr. The solvent of the reaction mixture was removed by distillation under reduced pressure, and the water layer was adjusted to pH 3 by the addition of 1 M hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate, and the filtrate was concentrated under reduced pressure to give a corresponding acid as a colorless solid (12.0 g, 94percent). This compound was used in the next step without further purification. Benzyl bromide (14.3 g, 83.33 mmol) was added dropwise to a suspension of this compound (10.0 g, 69.44 mmol) and anhydrous potassium carbonate (28.8 g, 208.3 mmol) in acetonitrile (100 ml) at room temperature, and the mixture was refluxed for 48 hr. The solvent of the mixture was removed by distillation under reduced pressure, the residue was diluted with water and was extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on silica gel column (hexane:ethyl acetate = 9:1) to give the tile compound as an oil (12.0 g, yield 75percent). 1H-NMR (400 MHz, CDCl3): delta (ppm) 7.39-7.34 (m, 5H), 5.12 (s, 2H), 3.95-3.92 (m, 2H), 3.42-3.36 (m, 2H), 2.30 (d, J = 7.2 Hz, 2H), 2.09-1.99 (m, 1H) 1.64-1.61 (m, 2H), 1.39-1.29 (m, 2H); MS (ESI): m/z 234 (M+).

103260-44-2, 103260-44-2 Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate 2773412, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Meiji Seika Pharma Co., Ltd.; MORINAKA, Akihiro; MAEBASHI, Kazunori; IDA, Takashi; HIKIDA, Muneo; YAMADA, Mototsugu; ABE, Takao; EP2737900; (2014); 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.344329-76-6,Tetrahydro-2H-pyran-4-carboxamide,as a common compound, the synthetic route is as follows.

Preparation 111; C- (Tetrahvdro-pyran)-metvlamine; In a 2L flask, charge tetrahydro-pyran-4-carboxylic acid amide (51g, 0. 395mol) and THF (1. 3L) and cool the reaction in an ice-bath. Add LAH (30g, 0.791) portion-wise. Stir the reaction at 10¡ãC for 16 hours and quench by the drop-wise addition of DI water (30ml), 15percent NaOH (30ml), and DI water (90mol). Stir the reaction at ambient temperature for 16 hours. Filter the salts and concentrate the filtrate under vacuum to give 36.79g clear oil of the title compound.

344329-76-6, The synthetic route of 344329-76-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2005/66126; (2005); 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.

A mixture of methyl tetrahydro-2/-/-pyran-4-carboxylate (7 g , 48.6 mmol) and 30percent aqueous ammonia (20 mL) was stirred in a closed bottle at r.t. for 18 h. The ammonia excess was removed under reduced pressure and the residue was crystallized from ethanol affording 5.6 g (89percent) of tetrahydro-2/-/-pyran-4-carboxamide. 1H NMR (401 MHz, DMSO-d6) delta ppm 7.21 (br. s., 1 H), 6.73 (br. s., 1 H), 3.90 – 3.80 (m, 2 H), 3.30 -3.23 (m, 2H), 2.36 – 2.24 (m, 1 H), 1.66 – 1.47 (m, 4 H), 110238-91-0

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

Reference£º
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; PULICI, Maurizio; TRAQUANDI, Gabriella; MARCHIONNI, Chiara; SCOLARO, Alessandra; COLOMBO, Nicoletta; WO2012/113774; (2012); 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.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.

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.

1228779-96-1, 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 fields.

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

1245724-46-2, (S)-Tetrahydro-2H-pyran-3-amine hydrochloride is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a dry 200 mL RBF was added di(2-pyridyl) thionocarbonate (1.69 g, 7.27 mmol, commerically available from Sigma Aldrich) and (3 S)-oxan-3 -amine hydrochloride (1.00 g, 7.27 mmol, commerically available from Accela ChemBio mc) in DCM (24 mL). N-Ethyl-Nisopropylpropan-2-amine (1.33 mL, 7.63 mmol, commerically available from Sigma Aldrich) in DCM (20 mL) was then added dropwise via a addition funnel over 20 mm at RT with stirring. The reaction mixture was stirred at RT for 15 h. The reaction mixture was concentrated in vacuo. The material thus obtained was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (24 g), eluting with a gradient of 0% to 50% EtOAc in heptane, to provide (S)-3-isothiocyanatotetrahydro-2H-pyran (0.99 g, 6.91 mmol, 95 % yield) as a colorless oil. 1H NMR (400 MHz, CDC13) oe 3.81-3.85 (m, 1H), 3.55-3.72 (m, 4H), 2.04-2.11 (m, 1H), 1.81-1.89 (m, 2H), 1.56-1.64 (m, 1H)., 1245724-46-2

1245724-46-2 (S)-Tetrahydro-2H-pyran-3-amine hydrochloride 60145922, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

61363-56-2, 2H-Pyran-3,5(4H,6H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

61363-56-2, A solution of 2-{[2-amino-5-(trifluoromethoxy)phenyl]disulfanyl}-4-(trifluoromethoxy)aniline (llb-2) (0.456 g, 1 .10 mmol) and oxane-3,5-dione (III- 5) (0.250 g, 2.19 mmol) in ethanol (7 ml) and triethylamine (0.5 ml) was refluxed for 16 hours. After completion of the reaction the mixture was concentrated to dryness under reduced pressure. The yield after flash chromatography (100-200 mesh size silica gel, 25-30% ethyl acetate in hexane) was 18 mg.

As the paragraph descriping shows that 61363-56-2 is playing an increasingly important role.

Reference£º
Patent; MEDEIA THERAPEUTICS LTD; RATILAINEN, Jari; GOLDSTEINS, Gundars; WO2014/191632; (2014); 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.85064-61-5,Tetrahydropyranyl-4-acetic acid,as a common compound, the synthetic route is as follows.,85064-61-5

General procedure: To (1 S, 1 ‘S)-l , 1 ‘-(5,5’-([ 1, 1 ‘-biphenyl]-4,4’-diyl)bis(lH-imidazole-5,2- diyl))bis(2,2-dimethylpropan- 1 -amine) tetrahydrochloride (75 mg, 0.124 mmol) was added 3-hydroxy-2,2,3-trimethylbutanoic acid (38.2 mg, 0.261 mmol) in DMF (3 mL) followed by DIPEA (0.174 mL, 0.996 mmol) at 0 ¡ãC. Then HATU (97 mg, 0.255 mmol) was added and stirred from 0 ¡ãC to RT for 6 h. The crude was dissolved in EtOAc (50 mL), washed with saturated NH4C1 (25 mL), 10percent NaHC03(25 mL), brine (25 mL), dried over Na2S04and concentrated under reduced pressure. The crude material was purified by reverse phase HPLC (ACN/water/TFA) to getTFA salt of Example B-69 (30 mg) as a white solid. HPLC (Condition B-1 and B-2): > 97percent homogeneity index. LC/MS (Condition B-12): Rt= 2.13 min.XH NMR (MeOD, 5 = 3.34 ppm, 400 MHz): delta 7.92-7.85 (m, 10 H), 4.94 (s, 2 H), 1.28 (s, 18 H), 1.16 (s, 12 H), 1.15 (s, 12 H). LC/MS: Anal. Calcd. for [M+H]+C42H61N604: 713.47; found 713.3

85064-61-5 Tetrahydropyranyl-4-acetic acid 2773575, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); 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.4295-99-2,4-Cyanotetrahydro-4H-pyran,as a common compound, the synthetic route is as follows.,4295-99-2

C-(4-Methyltetrahydropyran-4-yl)methylamine A mixture of tetrahydropyran-4-carbonitrile (5.00 g) and THF (50 ml) was admixed at 0 C. with lithium hexamethyldisilazide (1 M, 63 ml) and, after 90 minutes, methyl iodide (4.26 ml) was added dropwise with good cooling. After 12 hours, the reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. The residue was dissolved in THF (200 ml), and lithium aluminum hydride (3.79 g) was added. The mixture was boiled at reflux for 6 hours. Water (3.8 ml) and then sodium hydroxide solution (40%; 3.8 ml) were cautiously added dropwise to the cooled suspension. The precipitate was filtered off and the filtrate was concentrated. This afforded the product with the molecular weight of 129.20 (C7H15NO); MS (ESI): 130 (M+H+).

As the paragraph descriping shows that 4295-99-2 is playing an increasingly important role.

Reference£º
Patent; SANOFI; US2012/22039; (2012); 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.5631-96-9,2-(2-Chloroethoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.

5631-96-9, 2-(2-Chloroethoxy)tetrahydro-2H-pyran (148 g, 0.9 mol) was added to a mixture of aqueous sodium hydroxide solution (50 %, 888 ml), tetra-n-butylammonium hydrogen sulfate (305 g, 0.90 mol) and benzene (1480 ml) and the mixture was stirred at 600 C. After approx. 6 h, there was no more conversion (there was always starting material left). Diethyl ether (2 I) and water (2 I) were added and the phases were separated. The organic layer was washed with water (1 I) and the combined aqueous phases were extracted once with diethyl ether (1 I). The combined ethereal layers were dried over magnesium sulfate, and distilled with a vigreux column, first at normal pressure (most of the solvent – diethyl ether and benzene – was distilled off), then under reduced pressure, affording three fractions containing 2-(vinyloxy)tetrahydro-2/-/-pyran: F1 : 16 g (60mbar, 65 0C, 65 % product (+ benzene, 1H NMR) F2: 56 g (60mbar, 95 0C, 90 % product (+ tributylamine, 1H NMR) F3: 19 g (60-40mbar, 95 0C, 80 % product (+ tributylamine, 1H NMR)

As the paragraph descriping shows that 5631-96-9 is playing an increasingly important role.

Reference£º
Patent; NYCOMED GMBH; WO2008/95912; (2008); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics