Category: 85064-61-5

Chemistry is an experimental science, and the best way to enjoy it and learn about it is performing experiments.Introducing a new discovery about 85064-61-5, Name is Tetrahydropyranyl-4-acetic acid, 85064-61-5.

Synthesis and activity of putative small-molecule inhibitors of the F-box protein SKP2

The tetrahydropyran 4-(((3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-4-phenylbutyl)amino)methyl)-N,N-dimethylaniline was reported to disrupt the SCFSKP2 E3 ligase complex. Efficient syntheses of this tetrahydropyran derivative and analogues, including the des-dimethyl derivative 4-(((3-(tetrahydro-2H-pyran-4-yl)-4-phenylbutyl)amino)methyl)-N,N-dimethylaniline, are described. The enantiomers of the des-dimethyl compound were obtained using Evans’ chiral auxiliaries. Structure-activity relationships for these tetrahydropyrans and analogues have been determined by measurement of growth-inhibitory activities in HeLa cells, which indicated a non-specific mechanism of action that correlates with inhibitor lipophilicity. However, preliminary data with (R)-and (S)-4-(((3-(tetrahydro-2H-pyran-4-yl)-4-phenylbutyl)amino)methyl)-N,N-dimethylaniline showed enantioselective inhibition of the degradation of p27 in a cell-based assay that acts as a reporter of SKP2 activity.

85064-61-5, A reaction mechanism is the microscopic path by which reactants are transformed into products. Each step is an elementary reaction. In my other articles, you can also check out more blogs about 85064-61-5

Reference£º
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: N,N-Diisopropylethylamine (132 mL), 4-hydroxycyclohexane-1-carboxylic acid (33 mg) and propylphosphonicanhydride (1.6 mol/L N,N-dimethylformamide solution, 238 mL) were added to a solution of the compound (50 mg)obtained in Reference Example 14-1 in N,N-dimethylformamide (2 mL), and the mixture was stirred at room temperatureovernight. The mixture was purified by preparative LC-MS to give the title compound (Example 3-2) (25 mg) which wasa trans isomer as a highly polar compound, as a colorless amorphous substance.1H NMR (500 MHz, DMSO-d6) delta ppm 1.09 – 2.03 (m, 14.5 H) 2.85 – 2.98 (m, 0.5 H) 3.00 – 3.20 (m, 1.5 H) 3.21 – 3.40(m, 1 H) 3.78 – 4.08 (m, 3.5 H) 4.35 – 4.45 (m, 0.5 H) 4.48 – 4.58 (m, 1 H) 6.73 (s, 1 H) 7.36 – 7.96 (m, 3 H) 8.23 – 8.33 (m, 1 H).MS ESI/APCI Multi posi: 385 [M+H]+. The title compound (Example 3-3) (23.7 mg) which was a cis isomer as a less polar compound was obtainedas a colorless amorphous substance.1H NMR (600 MHz, DMSO-d6) delta ppm 1.13 – 2.02 (m, 12 H) 2.45 – 2.63 (m, 1.5 H) 2.84 – 2.95 (m, 0.5 H) 2.99 – 3.17 (m,1 H) 3.26 – 3.37 (m, 1 H) 3.71 – 4.09 (m, 4.5 H) 4.19 – 4.30 (m, 1 H) 4.38 – 4.46 (m, 0.5 H) 6.73 (br s, 1 H) 7.38 – 7.93(m, 3 H) 8.24 – 8.35 (m, 1 H). MS ESI/APCI Multi posi: 385 [M+H]+.

As the paragraph descriping shows that 85064-61-5 is playing an increasingly important role.

Reference£º
Patent; Taisho Pharmaceutical Co., Ltd.; TANAKA, Hiroaki; BOHNO, Ayako; HAMADA, Makoto; ITO, Yuji; KOBASHI, Yohei; KAWAMURA, Madoka; (235 pag.)EP3418276; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

85064-61-5, Tetrahydropyranyl-4-acetic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

85064-61-5, Example 13 To a mixture of tetrahydro-2H-pyran-4-ylacetic acid (89 mg), N,N-dimethyl formamide (1 muL), and dichloromethane (1 mL) was added oxalylchloride (54 muL), and the mixture was stirred at room temperature for 2 hours. The reaction liquid was concentrated under reduced pressure, and then toluene (1 mL) was added thereto, followed by further concentration under reduced pressure, to obtain crude tetrahydro-2H-pyran-4-yl acetyl chloride.

As the paragraph descriping shows that 85064-61-5 is playing an increasingly important role.

Reference£º
Patent; Astellas Pharma Inc.; US2011/53912; (2011); 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, To the solution of 3-[1 -(azetidin-3 -ylsulfonyl)-4-piperidyl] furo [3 ,2-b]pyridine (30.0 mg, 1 equiv.), 2-tetrahydropyran-4-ylacetic acid (12.6 mg, 1.2 equiv.) and EDCxHC1 (26.8 mg, 1.5 equiv.) in DMF (0.5 mL), HOBt (21.4 mg, 1.5 equiv.) and DIPEA (47 tL, 3.0 equiv.) were added and the resulting mixture was stirred at RT. After 2 hours, reaction mixture was diluted with EtOAc (10 mL) and washed with NaHCO3 sat. solution (3 x 10 mL) andbrine (15 mL). The organic layer was dried over Na2SO4, filtered and solvent was removed in vacuo. The obtained residue was purified by preparative LC-MS (ES mode, high pH method) to afford the expected product (17.4 mg). LCMS: MW (calcd): 447.55; MS (ES, m/z): 448.2 [M+H].

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

Reference£º
Patent; E-THERAPEUTICS PLC; RO?CIC, Maja; KOLUND?IC, Filip; ?IHER, Dinko; POLJAK, Tanja; VADLAMUDI, Srinivasamurthy; STUBBERFIELD, Colin; (503 pag.)WO2018/78360; (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.85064-61-5,Tetrahydropyranyl-4-acetic acid,as a common compound, the synthetic route is as follows.

85064-61-5, Oxalyl chloride (5 ml) and DMF (1 drop) were added to a solution of (TETRAHYDROPYRAN-4-YL) acetic acid (10 g) in DCM. The mixture was stirred for 3 h, then EVAPORATED IN VACUO and thoroughly azeotroped with toluene. The residue was dissolved in THF and added dropwise to a solution of (R)- BENZYLOXAZOLIDINONE (12.1 g) and nBuLi (2.5M in hexanes, 30 ml) in THF (200 ml) AT-78¡ãC. The solution was stirred for 2 h, then quenched with saturated aqueous ammonium chloride and evaporated in vacuo. The mixture was extracted with ethyl acetate, solvent washed with water and brine, dried and evaporated to give the title compound as a colourless solid (14 g). MS 304 (M + H).

As the paragraph descriping shows that 85064-61-5 is playing an increasingly important role.

Reference£º
Patent; CELLTECH R & D LIMITED; WO2004/113312; (2004); 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, Oxalyl chloride (5 mi) and DMF (1 drop) were added to a solution of Intermediate 28 (10 g) in DCM (100 ML). The mixture was stirred for 3 h, then EVAPORATED IN VACUO and thoroughly azeotroped with toluene. The residue was dissolved in THF (30 ml) and added dropwise to a solution of (R)- BENZYLOXAZOLIDINONE (12.1 g) and nBuLi (2.5M in hexanes, 30 ml) in THF (200 mi) AT-78C. The solution was stirred for 2 h, then quenched with saturated aqueous ammonium chloride (100 ml) and evaporated in vacuo. The mixture was extracted with EtOAc (100 ML), solvent washed with water (100 ML) and brine, dried (MGS04) and evaporated to give the title compound as a colourless solid (14 g). MS 304 (M + H)

As the paragraph descriping shows that 85064-61-5 is playing an increasingly important role.

Reference£º
Patent; CELLTECH R & D LIMITED; WO2004/113298; (2004); 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, To a solution of the compound prepared in Example 3 (183 mg) in dimethylformamide (3 mL) were added 4-tetrahydropyranylacetic acid (70 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (105 mg) and dimethylaminopyridine (155 mg) and the solution was stirred over night. After finishing the reaction, water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (methylene chloride: methanol=25:1). 4N hydrogen chloride/ethyl acetate solution was added to the reaction mixture, which was concentrated to give the compound of the present invention (79 mg) having the following physical data. TLC:Rf 0.49(chloroform:methanol=10:1); NMR (CD3OD): delta 0.98 (t, J=7.0 Hz, 3H), 1.24-1.69 (m, 8H), 1.87-2.40 (m, 7H), 2.95 (s, 3H), 3.02-3.48 (m, 6H), 3.49-3.61 (m, 2H), 3.87-3.95 (m, 2H), 4.12 (m, 1H), 4.27-4.30 (m, 2H), 7.03 (d, J=9.0 Hz, 2H), 7.06 (d, J=8.5 Hz, 2H), 7.29 (d, J=9.0 Hz, 2H), 7.49 (d, J=8.5 Hz, 2H).

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

Reference£º
Patent; ONO PHARMACEUTICAL CO., LTD.; EP1604981; (2005); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

85064-61-5, Tetrahydropyranyl-4-acetic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

85064-61-5, General procedure: Step 5a: The mixture of the crude compound 11a (1.0 eq) orcompound 11b (1.0 eq), HATU (1.5 eq), different acid (1.1 eq) andDIPEA (3.0 eq) in DCM was stirred at room temperature overnightunder N2 atmosphere. When the starting material wasconsumed completely, the mixture was washed with saturatedNaHCO3 solution and water, dried over anhydrous sodium sulfate,filtered and the filtrate was concentrated under reducedpressure to afford the crude product, which was purified bycolumn chromatography to afford the target compounds (2a, 2d,3a-3d,4a-4d, 5a, 5b, 5e-5h and 6a-6f). Enantiomers (S)-5c and(R)-5d were obtained by chiral HPLC separation of 5b.

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

Reference£º
Article; Tian, Jinlong; Sun, Nannan; Yu, Mingcheng; Gu, Xianfeng; Xie, Qiong; Shao, Liming; Liu, Jin; Liu, Li; Wang, Yonghui; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 37 – 48;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

85064-61-5,85064-61-5, Tetrahydropyranyl-4-acetic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 4 1 -(4-(4-(2-((2,6-difluorobenzyl)oxy)- 1,1,1 ,3 ,3 ,3-hexafluoropropan-2-yl)phenyl)-4-((4- fluorophenyl)sulfonyl)piperidin-l-yl)-2-(tetrahydro-2H-pyran-4-yl)ethanone Hunig’s base (8.57 mu, 0.049 mmol) was added to a mixture of 4-(4-(2-((2,6- difluorobenzyl)oxy)- 1,1,1 ,3 ,3 ,3 -hexafluoropropan-2-yl)phenyl)-4-((4- fluorophenyl)sulfonyl)piperidine (10 mg, 0.016 mmol), 2-(tetrahydro-2H-pyran-4- yl)acetic acid (2.83 mg, 0.020 mmol) and (benzotriazol-1- yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (8.68 mg, 0.020 mmol) in acetonitrile (0.5 mL) at room temperature. After 1 h at room temperature, LCMS analysis showed that the reaction was complete. The crude material was purified via preparative LC/MS with the following conditions: Column: Waters XBridge C18, 19 x 250 mm, 5- muiotaeta particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: 30- 100percent B over 20 minutes, then a 5-minute hold at 100percent B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give Example 4 (7.7 mg, 62percent yield). LC/MS (M+l): 738.2; LC retention time: 2.30 min (analytical HPLC Method B); IH NMR (500MHz, 1 : 1 mixture of CDCI3-CD3OD) delta ppm 7.64 (d, J=8.3 Hz, 2H), 7.47 – 7.39 (m, 3H), 7.30 – 7.22 (m, 2H), 7.06 – 6.96 (m, 4H), 4.71 (s, 2H), 4.25 (s, IH), 4.05 (d, J=13.9 Hz, IH), 3.96 – 3.85 (m, 2H), 3.46 – 3.37 (m, 2H), 3.04 (t, J=12.1 Hz, IH), 2.73 (d, J=12.2 Hz, IH), 2.67 – 2.55 (m, 2H), 2.52 – 2.24 (m, 4H), 2.06 – 1.93 (m, IH), 1.72 – 1.59 (m, 2H), 1.39 – 1.24 (m, 2H).

As the paragraph descriping shows that 85064-61-5 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; DUAN, Jingwu; DHAR, T.G. Murali; JIANG, Bin; KARMAKAR, Ananta; GUPTA, Arun Kumar; LU, Zhonghui; WO2015/103510; (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.85064-61-5,Tetrahydropyranyl-4-acetic acid,as a common compound, the synthetic route is as follows.,85064-61-5

S nthesis of Compound D6Step 1: Synthesis of Compound D2To a suspension of 0.55 g of LiAlH4 (13.9 mmol) in THF (10 mL) is added dropwise a solution of 2 g (13.9 mmol) of compound Dl in THF (10 mL) under nitrogen atmosphere (CAUTION: highly exothermic reaction.). Upon complete addition, the reaction is stirred at room temperature for 18 h. The reaction is cooled in an ice-bath and quenched with addition of 1M aqueous NH4C1 solution (2 mL). The resulting precipitate is removed by filtration through Celite and is rinsed with ethyl acetate (3 x 100 mL). The filtrate is dried over Na2S04, filtered and concentrated under reduced pressure to afford 1.63 g of compound D2 as a colorless oil. Yield: 90%; ES-MS m/z 131 [M+H]; 1H-NMR (500 MHz, CHLOROFORM-d) 5 ppm l.29 (2 H, qd, 7=12.08, 4.04 Hz), 1.50 (2 H, qd, 7=6.71, 1.37 Hz), 1.55 – 1.73 (3 H, m), 1.95 – 2.07 (1 H,m), 3.37 (2 H, t, 7=11.83 Hz), 3.66 (2 H, t, 7=6.03 Hz), 3.92 (2 H, dd, 7=11.44, 4.12 Hz)

As the paragraph descriping shows that 85064-61-5 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; RIETHER, Doris; ZINDELL, Renee, M.; ERMANN, Monika; WO2011/109324; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics