Category: 219823-47-9

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.219823-47-9,(R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

1-chloro-4-(beta-D-glucopyranos-1-yl)-2-[4-((S)-tetrahydrofuran-3-yloxy)-benzyl]-benzene 0.19 g (R)-3-(4-methylphenylsulfonyloxy)-tetrahydrofuran are added to a mixture of 0.20 g 1-chloro-4-(beta-D-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene and 0.29 g cesium carbonate in 2.5 ml dimethylformamide. The mixture is stirred at 75 C. for 4 h, before another 0.29 g caesium carbonate and 0.19 g (R)-3-(4-methylphenyl-sulfonyloxy)-tetrahydrofuran are added. After an additional 14 h stirring at 75 C. the mixture is cooled to ambient temperature and brine is added. The resulting mixture is extracted with ethyl acetate, the combined organic extracts are dried over sodium sulfate, and the solvent is removed. The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0?5:1). Yield: 0.12 g (49% of theory) Mass spectrum (ESI+): m/z=451/453 (Cl) [M+H]+, 219823-47-9

As the paragraph descriping shows that 219823-47-9 is playing an increasingly important role.

Reference£º
Patent; Boehringer Ingelheim International GmbH; US2007/249544; (2007); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.219823-47-9,(R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

(mixture of stereoisomers) (4-fluoro-2-hydroxyphenyl)-9-{[2-(trifluoromethoxy)phenyl]acetyl}-1,3,9-triazaspiro[5.5]- undecan-2-one (100 mg, 208 pmol, Intermediate 15), (3R)-oxolan-3-yl 4-methylbenzene-1 – sulfonate (75.5 mg, 312 pmol) and potassium carbonate (1 15 mg, 0.831 mmol) were mixed in dimethylformamide (1.2 ml_) and heated to 100 13 for 5 hours. The reaction was cooled down to room temperature, filtered and purified by preperative HPLC (Method 1 1) to give the title compound 65.0 mg (52 % yield). LC-MS (Method 4): Rt = 1.09 min; MS (ESIpos): m/z = 552 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) d [ppm]: 1.153 (0.98), 1.201 (1.22), 1.237 (2.54), 1.267 (2.20), 1.359 (2.88), 1.382 (2.54), 1.533 (1.66), 1.565 (1.46), 1.598 (1.56), 1.631 (1.32), 1.833 (0.83), 1.849 (1.12), 1.866 (1.37), 1.883 (1.17), 1.898 (1.07), 1.916 (1.12), 1.935 (1.37), 1.951 (1.71), 1.967 (1.80), 1.996 (0.88), 2.026 (0.78), 2.041 (0.73), 2.047 (1.32), 2.062 (1.71), 2.068 (0.73), 2.076 (0.59), 2.083 (1.46), 2.097 (0.98), 2.103 (0.59), 2.1 18 (0.54), 2.187 (1.41), 2.202 (2.00), 2.220 (2.29), 2.238 (1.90), 2.428 (16.00), 2.518 (11.56), 2.522 (7.02), 2.673 (2.05), 2.947 (1.22), 2.967 (1.17), 3.1 19 (0.88), 3.154 (1.61), 3.183 (2.29), 3.212 (1.27), 3.285 (3.37), 3.343 (7.22), 3.375 (4.00), 3.489 (0.68), 3.521 (1.71), 3.544 (3.41), 3.553 (4.15), 3.583 (4.10), 3.594 (3.85), 3.636 (2.88), 3.646 (7.37), 3.652 (10.29), 3.663 (5.66), 3.667 (3.46), 3.673 (5.02), 3.677 (3.27), 3.681 (4.10), 3.684 (4.73), 3.688 (4.10), 3.714 (3.80), 3.719 (4.24), 3.728 (3.32), 3.740 (4.59), 3.757 (8.05), 3.761 (6.34), 3.778 (8.00), 3.793 (6.98), 3.834 (3.46), 3.844 (3.76), 3.859 (1.85), 3.877 (2.34), 3.886 (2.29), 3.903 (1.90), 3.915 (1.66), 3.946 (1.71), 3.987 (2.05), 4.023 (0.88), 5.063 (2.39), 5.101 (2.29), 5.106 (2.15), 5.1 1 1 (2.29), 5.1 16 (2.15), 5.121 (1.41), 5.125 (1.12), 6.440 (6.15), 6.665 (5.66), 6.732 (1.46), 6.738 (1.80), 6.752 (3.85), 6.759 (3.66), 6.766 (2.93), 6.773 (3.80), 6.780 (2.20), 6.787 (1.61), 6.794 (1.51), 6.886 (3.12), 6.891 (3.17), 6.898 (2.88), 6.908 (2.63), 6.915 (3.22), 6.920 (3.22), 6.927 (2.63), 7.207 (6.10), 7.215 (12.34), 7.226 (9.85), 7.253 (10.68), 7.259 (8.68), 7.279 (3.66), 7.331 (2.00), 7.339 (4.00), 7.345 (4.00), 7.354 (3.56), 7.363 (3.95), 7.376 (1.76), 7.382 (1.22), 7.481 (3.61), 7.483 (4.20), 7.502 (4.68), 7.799 (5.95), 7.804 (1.80), 7.816 (1.76), 7.820 (5.32).

219823-47-9, As the paragraph descriping shows that 219823-47-9 is playing an increasingly important role.

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; GRAHAM, Keith; AIGUABELLA FONT, Nuria; HEINRICH, Tobias; BRAeUER, Nico; LANGE, Martin; BADER, Benjamin; PRECHTL, Stefan; LIENAU, Philip; NOWAK-REPPEL, Katrin; POTZE, Lisette; STEUBER, Holger; NIU, Haitao; WANG, Qiuwen; (248 pag.)WO2020/48827; (2020); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.219823-47-9,(R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

To a solution of toluene-4-sulfonic acid (R)-(tetrahydro-furan-3-yl) ester (1.5 g, 6.2 mmol) and Cs2C03 (1 .83 g, 5.6 mmol) in DMF (20 mL) was added 1 H-pyrazole-4-carboxylic acid ethyl ester (789 mg, 5.6 mol). The mixture was kept at 80C for 14 h. The volatiles were removed in vacuo and the residue was extracted with EtOAc (50 mL). The combined organic layers were washed with H20, dried over Na2S04 and evaporated to dryness. Flash chromatography (silica, petroleum ether: EtOAc 3:1 ) gave reagent 2 as a solid (1.07 g, 91 %). 1H NMR (CDCI3) delta 7.97 (s, 1 H), 7.90 (s, 1 H), 4.95-5.00 (m, 1 H), 4.27 (q, J = 6.4 Hz, 2 H), 4.01 -4.15 (m, 3 H), 3.90-3.96 (m, 1 H), 2.43-2.52 (m, 1 H), 2.27-2.34 (m, 1 H), 1.33 (t, J = 6.4 Hz, 3 H)., 219823-47-9

219823-47-9 (R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate 13837325, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; H. LUNDBECK A/S; ESKILDSEN, J¡ãrgen; WO2014/49133; (2014); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

219823-47-9, (R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-(3-(6-Hydroxypyridin-3-yl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile 10c (100 mg, 0.24 mmol) was placed in a reaction flask, followed by addition of (R)-tetrahydrofuran-3-yl-4-methylbenzenesulfonate 2a (116 mg, 0.48 mmol), cesium carbonate (235 mg, 0.72 mmol), and 3 mL of N,N-dimethylacetamide, successively. The reaction solution was warmed up to 60 C. and stirred for 2 hours. The reaction solution was cooled down to room temperature, mixed with 10 mL of saturated sodium chloride solution, and extracted with ethyl acetate (20 mL*3). The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by thin layer chromatography with elution system A to obtain the title compound (S)-4-(4,4-dimethyl-5-oxo-3-(6-((tetrahydrofuran-3-yl)oxy)pyridin-3-yl)-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile 24 (60 mg, yield 52.6%) as a white solid. MS m/z (ESI): 477.2 [M+1]; 1H NMR (400 MHz, CDCl3): delta 8.09-8.08 (m, 1H), 8.00-7.96 (m, 2H), 7.86-7.84 (m, 1H), 7.54-7.51 (m, 1H), 6.92-6.90 (m, 1H), 5.63-5.60 (m, 1H), 4.14-3.91 (m, 4H), 2.35-2.16 (m, 2H), 1.60 (s, 6H).

219823-47-9, The synthetic route of 219823-47-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Shanghai Hengrui Pharmaceutical Co., Ltd.; Jiangsu Hengrui Medicine Co., Ltd.; Lu, Hejun; Sun, Piaoyang; Fei, Hongbo; Jiang, Hongjian; Wang, Haowei; Dong, Qing; US2015/225381; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.219823-47-9,(R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

A microwave vessel was charged with 1-[8-fluoro-6-methoxy-4-methyl- 3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl]-trans-2-methylpiperidin-4-amine (Int- 236-4, 58 mg, 0.15 mmol), (3R)-oxolan-3-yl 4-methylbenzene-1-sulfonate (Int-172-11, 146 mg, 0.56 mmol), DIPEA (0.105 mL, 0.56 mmol) and CH3CN (0.9 mL). The mixture was heated for 12 hours at 120oC in a microwave reactor. The mixture was partitioned between EtOAc and an aqueous Na2CO3 solution, drying the organic fraction over sodium sulfate, and concentrating to 170 mg of an orange oil. The crude product was purified by column chromatography eluting with a gradient of 0-60% EtOAc/hexanes, followed by a gradient of 0-10% MeOH/DCM to give the mixture of diastereomers as a yellow solid (38 mg, 56% yield). The mixture can be separated to give the individual diasteromers using a phenomenex Lux 5mu cellulose-4 column (250mmx4.6mm, hexane:ethanol:DEA (73:27:0.1), 1 mL/min, retention time: 7.2 min, 8.9 min. LCMS: (M+1) m/z = 356.1., 219823-47-9

219823-47-9 (R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate 13837325, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; THE SCRIPPS RESEARCH INSTITUTE; BLACKTHORN THERAPEUTICS, INC.; ROBERTS, Edward; GUERRERO, Miguel A.; URBANO, Mariangela; ROSEN, Hugh; JONES, Rob; LAXAMANA, Candace Mae; ZHAO, Xianrui; TURTLE, Eric Douglas; (331 pag.)WO2018/170492; (2018); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.219823-47-9,(R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

N-alpha-Methyl-lH-pyrazol-S-ylVS-rrphenylmethvDoxyi-S-Cbeta^-tetrahvdrofuran-S- yloxylbenzamide EPO A suspension of 3-hydroxy-N-(l-methyl-lH-pyrazol-3-yl)-5- [(phenylmethyl)oxy]benzamide (450 mg, 1.39 mmol), (3i?)-tetrahydrofuran-3-yl 4- methylbenzenesulfonate (507 mg, 2.09 mmol) and potassium carbonate (481 mg, 3.48 mmol) in acetonitrile (5 mL) was stirred in a Smith Creator microwave at 160C for 3 hours. The solvent was removed in vacuo and ethyl acetate added. The organics were washed with water (40 mL), brine (40 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give a yellow foam which was chromatographed on silica, eluting with a gradient of 0-100% ethyl acetate in isohexane, to give the title compound as a white foam (452 mg). 1R NuMR delta (CDCl3): 2.09 – 2.14 (1Eta, m), 2.14 – 2.24 (1Eta, m), 3.68 (3Eta, s), 3.86 – 3.91 (IH, m), 3.94 – 3.98 (3H, m), 4.89 (IH, s), 5.03 (2H, s), 6.64 (IH, t), 6.85 (IH, s), 6.96 (IH, d), 7.07 (IH, t), 7.27 (IH, m), 7.33 – 7.41 (5H, m), 9.31 (IH, s); m/z 394 (M+H)+.

219823-47-9 (R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate 13837325, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/7040; (2007); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

219823-47-9, (R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of tri-tert-butyl hydrazine-1,1,2-tricarboxylate (58.5 g, 0.95 eq., prepared as per Angew. Chem. Tnt. Ed. 1996, 35, No. 22, 2626-2627) in dimethylsulfoxide (180 ml), was added cesium carbonate (90.77 g, 1.5 eq.), followed by stirring for 30 minutes at 20 to 30C. (R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate (45.0 g, 1.0 eq.) was added into the reaction mass, followed by increase of temperature to 50 to 55C. The resulting reaction mass was stirred at 50 to 55C till tri-tert-butyl hydrazine-1,1,2-tricarboxylate is less than 0.25% monitored by HPLC area %. After completion of the reaction, the reaction mass was cooled to 20 to 25C, followed by addition of water (225 ml) and methyl tert-butyl ether (450 ml). The resulting biphasic mixture was stirred for 10 minutes followed by layer separation. The resulting organic layer was washed with an aqueous sodium chloride solution (225m1) followed by solvent evaporation under reduced pressure to give crude (5)-tri-tert-butyl 2-(tetrahydrofuran-3-yl)hydrazine- 1,1 ,2-tricarboxylate (68.34 g). The crude material was recrystallized using a mixture of methyl tert-butyl ether and n-heptane (22.5 ml:112.50 ml) to give pure (5)-tri-tert-butyl2-(tetrahydrofuran-3-yl)hydrazine- 1,1 ,2-tricarboxylate (57.96 g , 77.53%).Mass [M+Hj: 402.80Purity by HPLC: 99.59% areaSpecific Optical Rotation (C=1, Methanol): -8.553Melting point (DSC method): 62.7 1C

As the paragraph descriping shows that 219823-47-9 is playing an increasingly important role.

Reference£º
Patent; EISAI R&D MANAGEMENT CO., LTD.; KHILE, Anil Shahaji; NAYAK, Ranjeeta; DIXIT, Girish; (30 pag.)WO2016/21192; (2016); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

219823-47-9, (R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Under the protection of argon gas, the 6 – (4-hydroxy -1,2-dihydro-furo [3,2-f] quinoline-9-yloxy)-N-methyl-1-naphthalene carboxamide 1p (20 mg, 0 . 052mmol), (R)-tetrahydrofuran-3-yl tosylates 13a (under WO2007007886 relates to the method of preparing) (63 mg, 0 . 26mmol), cesium carbonate (127 mg, 0 . 39mmol) and 2 ml in dimethyl acetamide is put into the reaction bottle, for 60 C reaction under 30 minutes. Cooling, adding 2 ml water and 5 ml ethyl acetate, separating, the aqueous phase is extracted with ethyl acetate (3 ml ¡Á 2), combined with the phase, saturated sodium chloride solution used for washing, drying by anhydrous magnesium sulphate, filtered, filtrate concentrated under reduced pressure, in order to thin-layer chromatography for purification of the resulting product A developing agent system, to obtain the title product (S) – 6 – ((4 – ((tetrahydrofuran-3-yl) oxy) – 1,2-dihydro-furo [3,2-f] quinolin-9-yl) oxy)-N-methyl-1-naphthalene carboxamide 13 (40 mg, pale yellow solid), yield: 67.0%.

As the paragraph descriping shows that 219823-47-9 is playing an increasingly important role.

Reference£º
Patent; Shanghai Hengrui Pharmaceutical Co., Ltd.; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Lv Hejun; Chen Yiqian; Wang Shenglan; Hu Qiyue; Zheng Suxin; (73 pag.)CN103382206; (2016); B;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem