Category: 219823-47-9

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

A suspension of 3-hydroxy-N-(l-rnethyl-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 1600C 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 zso-hexane, to give the title compound as a white foam (452 mg). 1H NMR delta (CDCl3): 2.09 – 2.14 (IH, m), 2.14 – 2.24 (IH, m), 3.68 (3H, 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

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

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/7041; (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

In a round bottom flask, 1.2 g compound of Formula (II), 1.2 g cesium carbonate, 0.81 (R)-tetrahydrofuran-3-yl-4-methylbenzenesulfonate and 18 mL DMF or DMSO were added at 25 C. to 35 C. The reaction mixture was heated to 35 to 40 C. and stirred for 24-36 hrs. The reaction mixture then cooled to 25 C. to 35 C. 40 mL water and 20 ml toluene were added stirred for 15-20 minutes. Layers were separated. The aqueous layer was extracted with dichloromethane, dried over sodium sulfate. The solvent was distilled out under vacuum. 10 mL ethanol was added and stirred for 30 minutes. The reaction mixture was stirred at 0-5 C. for an hour. The product was filtered and washed with pre-cooled ethanol and dried to obtain empagliflozin., 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; CADILA HEALTHCARE LIMITED; DESAI, Sanjay Jagdish; PARIHAR, Jayprakash Ajitsingh; RUPAPARA, Mahesh Laljibhai; GANGWAR, Pranav Jitendra; GHODASARA, Hardik Bhikhubhai; (30 pag.)US2017/247356; (2017); 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.

Step 2: Synthesis of 4-Bromo-1 -[(3S)-tetrahydrofuran-3-yl]pyrazole 3.6A mixture of 650 mg [(3R)-tetrahydrofuran-3-yl] 4-methylbenzenesulfonate, 400 mg 4-bromo- 1 H-pyrazole and 1 .40 g cesium carbonate in 10 mL Nu,Nu-dimethylformamide (DMF) was stirred at 65 C for 6 h. Additional 20 mg 4-bromo-1 H-pyrazole were added and the reaction mixture was stirred at 65 C overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (cyclohexane/ethyl acetate 9:1 ->1 :1 ) to yield 476 mg of 4-bromo-1 -[(3S)-tetrahydrofuran-3- yl]pyrazole 3J3 as solid.Analysis: MS: M+H = 217 / 219

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; DAHMANN, Georg; HOFFMANN, Matthias; KLICIC, Jasna; LAMB, David James; MCCARTHY, Clive; NAPIER, Spencer; PARRISH, Karen; SCOTT, John; SWANTEK FITZGERALD, Jennifer L.; WALKER, Edward; WO2015/140054; (2015); 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

Intermediates E-I and E-II 4-Bwmo-l-(S)- tetrahydro-furan-3-yll-lH-pyridin-2-one and 4-bromo-2-[(S)-tetrahydro- furan-3 -yloxyl -pyridine A mixture of 4-bromo-lH-pyridin-2-one (0.50 g), (i?)-toluene-4 -sulfonic acid tetrahydro- furan-3-yl ester (0.40 g), and potassium carbonate (0.80 g) in dimethylsulfoxide (5 mL) was stirred at 80 0C overnight. After cooling to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO/O, and concentrated. The residue was purified by HPLC on reversed phase (acetonitrile/water) to afford the title compounds in separate fractions.4-Bromo-l-[(S)- tetrahydro-furan-3-yl]-lH-pyridin-2-one: Yield: 0.11 g (16% of theory); Mass spectrum (ESI+): m/z = 244/246 (Br) [M+H]+.4-Bromo-2-[(S)-tetrahydro-furan-3-yloxy]-pyridine: Yield: 0.36 g (56% of theory); Mass spectrum (ESI+): m/z = 244/246 (Br) [M+H]+.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; HIMMELSBACH, Frank; WO2010/89303; (2010); 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 mixture of 1.93 g (7.97 mmol) of (3R)-tetrabydrofuran-3-yl 4- methylbenzenesulfonate (WO 2016/91776 A1 (16.06.2016) EVOTEC AG), 2.46 mL (15.9 mmol) of ethyl piperidine-4-carboxyiate, 39 mL of acetonitrile and 4.4 g (31.9 mmol) of K2CO3 was stirred at 70C for 24 h, then cooled to room temperature and diluted with ethyl acetate. The so obtained mixture was washed with water and this water phase was discarded. The organic layer was washed with 1 M HCI solution and this acidic water phase was alkaiified with 10% K2CO3 solution, extracted with ethyl acetate, the combined organic layers were dried over Na2S04, filtered and concentrated. The residue was purified by flash column chromatography using dichloromethane : methanol = 91 :9 as eluent to yield 603 mg (27%) of the title compound. GC-MS (El) m/z 227., 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; RICHTER GEDEON NYRT.; BASKA, Ferenc; BOZO, Eva; BATA, Imre; SZONDINE KORDAS, Krisztina; VUKICS, Krisztina; (293 pag.)WO2019/116324; (2019); 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.

Intermediate 84-Bromo-1 -[(SHetrahvdro-furan-3-nuPi-Iota H-pyridin-2-one; A mixture of 4-bromo-1 H-pyridin-2-one (0.50 g), (/:?)-toluene-4-sulfonic acid tetrahydrofuran-3- yl ester (0.40 g), potassium carbonate (0.80 g), and dimethylsulfoxide (5 mL) was stirred at 80 ‘C overnight. After cooling to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgS04), and concentrated. The residue was purified by HPLC on reversed phase (acetonitrile/water) to afford the title compound [besides, 4-bromo-2-[(S)-tetrahydro- furan-3-yloxy]-pyridine was isolated in 0.36 g (56% of theory)]. Yield: 0.1 1 g (1 6% of theory); LC (method 3): tR = 2.18 min; Mass spectrum (ESI+): m/z = 244/246 (Br) [M+H]+.

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

Reference£º
Patent; VITAE PHARMACEUTICALS, INC.; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LEFTHERIS, Katerina; ZHUANG, Linghang; TICE, Colin, M.; SINGH, Suresh, B.; YE, Yuanjie; XU, Zhenrong; HIMMELSBACH, Frank; ECKHARDT, Matthias; WO2011/159760; (2011); 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 (1 R,4R)-5-(6-(6-(3-azabicyclo[3. 1 .0]hexan-6-yl)-5-methyl-1 H-indazol-1 -yl)-2- methylpyrimidin-4-yl)-2-oxa-5-azabicyclo[2.2. 1 ]heptane (150 mg, 0.37 mmol) in MeCN (20 mL) was added (R)-tetrahydrofuran-3-yl 4-methylbenzenesulfonate (271 mg, 1.12 mmcl) and K2C03 (154 mg, 1.12 mmcl) at ii under N2. The reaction mixture was stirred at 110 C for 24h. The mixture was purified by silica gel chromatography eluted with EtOAc and flash columnto give the product as a white solid (35 mg, yield: 19%).IH NMR (400 MHz, CDCI3) oe 8.52 (s, 1H), 8.03 (s, IH), 7.46 (s, 1H), 6.66 (s, 1 H), 5.25 (m,0.65H), 4.73 (s, 1H), 3.97-3.93 (m, 1H), 3.92-3.90 (m, 2H), 3.88-3.83 (m, 2H), 3.79-3.77 (m,1H), 3.65-3.52 (m, 2H), 3.29-3.27 (m, 1H), 3.18-3.16 (m, IH), 3.07-3.03 (m, 1H), 2.61-2.50(m, 5H), 2.42 (s, 3H), 2.41-2.40 (m, 1H), 2.06-1.91 (m, 4H), 1.88 (m, 2H).LC-MS [mobile phase: from 90% water (0.1% FA) and 10% MeCN (0.1% FA) to 5% water (0.1% FA) and 95% MeCN (0.1% FA) in 2.6 mm]: Rt 1.12 mm; MS Calcd: 472.26, MS Found: 473.5 [M + H]., 219823-47-9

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

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; DING, Xiao; REN, Feng; SANG, Yingxia; XING, Weiqiang; ZHAN, Yang; ZHAO, Baowei; (357 pag.)WO2018/137593; (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.

A 10-necked flask was charged with 10 (54.90 g, 100 mmol) and acetonitrile (275 mL)Add potassium carbonate(27.64 g, 200 mmol) and(3R) -tetrahydrofuran-3-p-toluenesulfonate(29.07 g, 120 mmol),Room temperature reaction overnight. The reaction was terminated by removing part of the acetonitrile, adding water (275 mL) andEthyl acetate (275 mL) and the aqueous phase was extracted again with ethyl acetate (137 mL)Combined with organic saturated brine washed twice (137mL), dried over sodium sulfate,After concentration, the crude key intermediate compound 11 (53.86 g, 87%) was re-crystallized with petroleum ether ethyl acetate.

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

Reference£º
Patent; Hangzhou Kechao Biological Technology Co., Ltd.; Zheng Xuchun; Zhang Yiping; Wu Yihua; (18 pag.)CN107163092; (2017); A;,
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.

4-(3-(3-Fluoro-4-hydroxyphenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2 -(trifluoromethyl)benzonitrile 1e (80 mg, 0.19 mmol) was placed in a reaction flask, followed by addition of (R)-tetrahydrofuran-3-yl-4-methylbenzenesulfonate 2a (92 mg, 0.38 mmol, prepared by a well known method “Journal of Medicinal Chemistry, 2011, 54 (12), 4092-4108”), cesium carbonate (186 mg, 0.57 mmol) and 3 mL of N,N-dimethylacetamide successively. The reaction solution was warmed up to 60C. After reacting for 2 hours, the reaction solution was cooled down to room temperature, mixed with 15 mL of water and extracted with ethyl acetate (25 mL ¡Á 3). The organic phases were combined, washed with saturated sodium chloride solution (10 mL¡Á3), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under the reduced pressure and the residue was purified by thin layer chromatography with elution system B to obtain the title compound (S)-4-(3-(3-fluoro-4-((tetrahydrofuran-3-yl)oxy) phenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile 2 (73 mg, yield 77.9%) as a pale yellow solid. MS m/z (ESI): 494.4 [M+1] 1H NMR (400 MHz, CDCl3): delta 8.00-7.06 (m, 2H), 7.84 (q, 1H), 7.08 (d, 1H), 7.04-7.03 (m, 2H), 5.04-5.02 (m, 1H), 4.07-3.94 (m, 4H), 2.29-2.24 (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; EP2894151; (2015); 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 solution of Acetic acid (5S,6S,7R,8S)-7,8-diacetoxy-5-[4-chloro-3-(4-hydroxy-benzyl)-phenyl]-4-oxa-spiro[2.5]oct-6-yl ester (120 mg, 0.22 mmole) in DMF (3 mL), cesium carbonate (85 mg, 0.27 mmole), Toluene-4-sulfonic acid (R)-(tetrahydro-furan-3-yl)ester (65 mg, 0.27 mmole) was added at room temperature and heated at 60 C. for 6 hours. The reaction mixture was diluted with water (20 mL), and extracted with dichloromethane (2¡Á50 mL). Crude (5S,6S,7R,8S)-5-(4-chloro-3-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)phenyl)-4-oxaspiro[2.5]octane-6,7,8-triyl triacetate obtained after the removal of solvent used for next step without purification., 219823-47-9

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

Reference£º
Patent; NOVARTIS AG; US2012/196813; (2012); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem