Heterocyclic Building Blocks-Tetrahydropyrans

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, N-tert-Butyloxycarbonyl-N-[(tetrahydropyranyl)oxy] ethyl-O-benzylhydroxylamine (30) To a stirred solution of N-tert-butyloxycarbonyl-O-benzylhydroxylamine 28 (5.79 g, 25.96 mmol) in dry DMF (50 ml) was added NaH (60%, 1.2 g, 30 mmol) slowly during 15 min period under argon atmosphere at 0 C. The reaction was allowed to stir at 0 C. for 30 min and at room temperature for 1 h. 1-Chloro-2-(tetrahydropyranyl)oxy-ethane 29 (4.95 g, 30 mmol) was added and the reaction mixture was heated at 80 C. for 12 h. The reaction was cooled and evaporated to dryness. The residue was suspended in water (50 ml), pH of the solution adjusted to 7 and extracted in EtOAc (150 ml). The EtOAc extract was washed with water and brine, dried and evaporated to dryness. The residue was purified by flash chromatography over silica gel using hexane?CH2 Cl2 as the eluent. The required fractions were collected and evaporated to give 6.0 g (66%) of an oily product. 1 H-NMR (CDCl3): delta1.48 (s, 9H, Boc), 1.49-1.84 (m, 6H, 3.CH2), 3.48-3.70 (m, 4H, 2.CH2), 3.86 (m, 2H, CH2), 4.60 (t, 1H, CH), 4.84 (s, 2H, CH2 Ph) and 7.32-7.42 (m, 5H, Ph).

The synthetic route of 5631-96-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ICN Pharmaceuticals, Inc.; US5969135; (1999); A;,
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.83-87-4,(3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate,as a common compound, the synthetic route is as follows.

83-87-4, 1,2,3,4,6-tetraacetylglucose (5.5 g, 7.1 mmoles) and hydrazine acetate (0.8 g, 1.2 eq) were dissolved in 20 mL of DMF. After 1 hour, DMF was removed under reduced pressure, the crude product was dissolved in 50 mL of ethyl acetate and washed twice with 20 mL of water. The organic layer was dried over sodium sulfate. 2 g of product was obtained after chromatography (cyclohexane/AcOEt 6/4) (yield: 65%). The characterization data were consistent with the chemical structure.

The synthetic route of 83-87-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Grinstaff, Mark W.; Barthelemy, Philippe; Prata, Carla; Moreau, Louis; US2006/241071; (2006); 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.53911-68-5,4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.,53911-68-5

Prepared by dissolving an equimolar mixture of 3-(4-chlorophenyl)glutaric anhydride and commercial 5-chloro-2-hydroxyaniline in boiling dichloromethane. Upon cooling to rt product precipitates and yields after isolation 87% of N-(2-hydroxy-5-chlorophenyl)-3-(4-chlorophenyl)glutaramic acid as colourless crystals

53911-68-5 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione 104639, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
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,40191-32-0

Into a 8-mL vial, were placed methyl (R)-3-(trifluoromethyl)-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine-8-carboxylate (25 mg, 0.09 mmol, 1 equiv), CH2Cl2 (1.5 mL), Et3N (28 mg, 0.28 mmol, 3 equiv) and tetrahydro-2H-pyran-4-carbonyl chloride (16 mg, 0.11 mmol, 1.2 equiv). The resulting solution was stirred for 16 h at room temperature. The crude product was purified by Prep-TLC (EtOAc/pet. ether, 1:1) to afford the title compound as yellow oil (35 mg, 99% yield). MS: (ES, m/z): 388 [M+H]+.

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

Reference£º
Patent; Forma Therapeutics, Inc.; Zheng, Xiaozhang; Ng, Pui Yee; Han, Bingsong; Thomason, Jennifer R.; Zablocki, Mary-Margaret; Liu, Cuixian; Davis, Heather; Rudnitskaya, Aleksandra; Lancia, JR., David; Bair, Kenneth W.; Millan, David S.; Martin, Matthew W.; (190 pag.)US2016/222028; (2016); 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.951127-25-6,tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

55c (1.09 g, 1.78 mmol) was dissolved in N, N-dimethylacetamide (15 mL)Intermediate 1 (0.64 g, 1.95 mmol) was added to the reaction system at room temperature for 30 minutes. The reaction system was cooled to 0 C and sodium borohydrogen triacetate (0.65 g, 3.47 mmol) was added. The reaction was continued for 30 minutes and 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 compound was dissolved in dichloromethane and treated with dichloromethane ¡Á 3), the organic phase was combined, washed with saturated brine solution (50 mL x 1), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated and purified by column chromatography (dichloromethane / methanol (v / v) = 20 : 1) to give a yellow solid 55d (0.68 g, yield 70%)., 951127-25-6

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.951127-25-6,tert-Butyl ((2R,3S)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

951127-25-6, Compound 3(200 mg, 0.611 mmol) and HSCH2CH2SH (0.11 mL, 1.53 mmol) were dissolved in DCM (10 mL) and treated with BF3 etherate (0.077 mL, 0.611 mmol) at RT. The resulting solution was stirred at RT for 1 h, and quenched with sat. aq. NaHCO3 solution. The organic phase was separated andextracted with DCM for several times. Combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 60 – 90 oC PE:EtOAc =10:1) to yield the product 8 (white solid, 212 mg, 0.525 mmol, 86%). M.p. 156.6 – 159.0 (dichloromethane); Rf 0.2 (10 : 1, petroleum ether : EtOAc); [alpha]D -7.88 (c 0.165, CHCl3) ; HPLC tR 3.6min; 1H NMR (600 MHz, CDCl3) delta 7.28 (s, 1H, ArH), 6.95 (s, 2H, ArH), 4.45 (d, J = 9.0 Hz, 1H, NHBoc),4.42 (d, J = 9.9 Hz, 1H, H-1), 4.00 (dd, J = 12.0 Hz, 1.8 Hz, 1H, H-5), 3.86 (d, J = 9.0 Hz, 1H, H-2), 3.74(d, J = 11.6 Hz, 1H, H-5?), 3.34 (ddd, J = 22.8, 12.0, 5.8 Hz, 4H, Dithiolane-CH2), 2.63 (d, J = 12.9 Hz, 1H,H-3), 2.19 – 2.01 (m, 1H, H-3?), 1.27 (s, 9H, C(CH3)3); 13C NMR (151 MHz, CDCl3) delta 159.10 (d, J C-F =243.0 Hz, ArC), 156.29 (d, J C-F = 240.6 Hz, ArC), 154.55 (C=O), 128.00 (dd, J C-C-F = 15.5, 7.9 Hz, ArC),116.40 – 116.13 (m, ArC), 116.13 – 115.81 (m, ArC), 115.34 – 115.07 (m, ArC), 79.75 (C(CH3)3), 77.84(C-5), 76.01 (C-1), 64.88 (C-4), 52.80 (C-2), 46.52 (C-3), 38.96 (Dithiolane-CH2), 38.78(Dithiolane-CH2), 28.24 (C(CH3)3); HRMS (ESI+) calcd. For C18H23F2NNaO3S2+426.0980, found426.0968.

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

Reference£º
Article; Li, You; Liu, Tongchao; Li, Chungang; Xiong, Bing; Zhao, Dongmei; Cheng, Maosheng; Chen, Guohua; Shen, Jingkang; Chen, Yue-Lei; Synthetic Communications; vol. 47; 4; (2017); p. 357 – 363;,
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

15a (342 mg, 0.656 mmol) and Intermediate 1 (236 mg, 0.722 mmol) were dissolved in N, N-dimethylacetamide (5 mL) and stirred at room temperature for 0.5 hour, A solution of sodium tris (acetoxy) borohydride (375.3 mg, 1.771 mmoL) was added to the ice bath,Stir at room temperature for 2 hours. To the reaction solution was added concentrated aqueous ammonia (10 mL) and saturated sodium chloride solution (30 mL)And the mixture was stirred for 0.5 hour. The filtrate was extracted with dichloromethane (30 mL x 3). The filter cake was dissolved with the combined organic phase, dried over anhydrous sodium sulfate, filtered and dried by rotary separation. The residue was purified by silica gel column chromatography (Dichloromethane / methanol (v / v) = 30: 1 to 20: 1, a small amount of aqueous ammonia was added) to give a yellow solid as a yellow solid 15b (200 mg, yield 59%).

951127-25-6, 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

65412-03-5, 4-(2-Aminoethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

65412-03-5, 2-(tetrahydro-2H-pyran-4-yl)ethan-1-amine (0.5 mmol) and methyl 2-(2-(chloromethyl)phenyl)acetate (0.5 mmol) were mixed in 5ml of DMF; DIPEA (0.75 mmol) was added. The mixture was heated at 80 C for 5 h, cooled; solvent was removed by evaporation and residue was purified by HPLC. Yield: 41%. 1H NMR (400 MHz, Chloroform-d) d 7.62 (ddt, J = 16.3, 11.9, 5.3 Hz, 3H), 4.87 (s, 2H), 4.27 – 4.18 (m, 2H), 3.88 (d, J = 8.7 Hz, 4H), 3.66 (td, J = 11.7, 2.0 Hz, 2H), 3.56 (s, 2H), 2.91 (dd, J = 3.8, 1.9 Hz, 1H), 2.05 (d, J = 12.9 Hz, 2H), 1.88 (t, J = 6.4 Hz, 3H), 1.68 – 1.57 (m, 2H). m/z=260.2

65412-03-5 4-(2-Aminoethyl)tetrahydro-2H-pyran 2773198, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; KAHNE, Daniel, E.; BAIDIN, Vadim; (331 pag.)WO2019/140265; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

220641-87-2, N-Methyltetrahydro-2H-pyran-4-amine is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

N-Methyl-N-(tetrahydro-2H-pyran-4-yl)carbamoyl chloride (No. III.10) 248 g (2.5 mol) of phosgene, 96 g (0.83 mol) of N-methyl-N-(tetrahydro-2H-pyran-4-yl)amine and 84 g (0.83 mol) of triethylamine were reacted by the method of the process described in Intermediate 1.2. Yield 108 g. 1H NMR (250 MHz, in CDCl3): delta=1.60-1.95 (m, 4H), 2.94 and 3.01 (2 s, together 3H), 3.35-3.55 (rm, 2H), 3.95-4.10 (m, 2H), 4.27-4.46 (m, 1H).

220641-87-2, 220641-87-2 N-Methyltetrahydro-2H-pyran-4-amine 6991950, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BASF Aktiengesellschaft; US6277790; (2001); 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.

The quantity of reagents and materials used in the following procedure were based on the quantity of N-(l-Methyl-l-phenylethyl)-lH-indazole-3-carboxamide obtained in the preceding step, as indicated. A solution of N-(l -methyl- l-phenylethyl)-lH-indazole-3-carboxamide (1.0 molar eq.) in anhydrous DMF (5 volumes) was mixed with anhydrous potassium carbonate (5.84 molar eq.). (Tetrahydro-2H-pyran-4-yl) methyl 4-methylbenzenesulfonate (1 molar eq.) was added portion wise over a period of 5 minutes at ambient temperature to the reaction mixture. The resulting reaction mixture was heated to 70C for at least 15 hours using an oil bath. The reaction mixture was evaporated at a 40C bath temperature under reduced pressure to remove the DMF. The evaporated residue was mixed with ethyl acetate (5 volumes) and then poured into ice (5 weight equivalents). The mixture was stirred until the ice melted. The bilayer was separated and the aqueous layer extracted with ethyl acetate (4 x 3 volumes). The combined extracts were washed with 50% saturated sodium carbonate solution (4 x 1 volume), then dried over sodium sulfate and filtered. The filtrate was evaporated at a 40 bath temperature and co-evaporated with ethyl acetate (3 x 2.5 volumes). The resultant residue was redissolved and hot ethyl acetate (4 volumes) and filtered through 60 angstrom silica (2.5 volumes) topped with a layer of anhydrous sodium sulphate. The filter bed was washed with hot ethyl acetate (2 volumes per fraction) until all of the product was released. Product containing fractions were evaporated with a bath temperature of 40C. The crude product was triturated with methyl tert-butyl ether (MTBE)(2 volumes) at room temperature of the 2 hours, and then in an ice bath for one hour. The suspension was filtered, then rinsed with cold MTBE (4 x 1 volume). The resulting white solid was then dried under vacuum to constant weight, mp 112.7 ¡À 0.5 . IR vmax/cm_1 3328, 1664 (amide). lU NMR (400 MHz, DMSO-d6) delta 8.03 (1H, d, HI), 7.97 (1H, s, H5), 7.82 (1H, d, H4), 7.41-7.44 (3H, m, H2, H3), 7.33 (2H, dt, H8), 7.20 (2H, dd, H7), 4.41 (2H, d, H10), 3.84 (2H, d, H13), 3.25 (2H, m, H14), 2.23 (1H, m, H15), 1.74 (6H , s, H6), and 1.39 (4H, m, Hl l, H12). MS (ESI+) m/z 378 (MH+). Anal. Calcd for C23H27N3O2: C, 73.18; H, 7.21; N, 11.13. Found: C, 73.44; H, 7.22; N, 11.23. 1 13 H and i3C NMR scans for SGT-42 are provided in Figures 1 and 2, respectivley., 101691-65-0

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

Reference£º
Patent; BOWDEN, Matthew James; WILLIAMSON, James Peter Bernard; WO2014/167530; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics