Heterocyclic Building Blocks-Tetrahydrofuran

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5061-21-2,2-Bromo-4-butanolide,as a common compound, the synthetic route is as follows.

5061-21-2, Example I: Synthesis of 3- (4-nitrophenvnsulfanyl1dihvdrofuran-2(3H)-oneTo a solution of p-nitro thiophenol (10.0 g, 0.0645 mol) in dichloromethane (75 mL) under argon atmosphere at about 0C, was added triethyl amine (19.4 g, 0.1935 mol) and then added a solution of bromolactone (11.1 g, 0.067 mol) in dichloromethane (75 mL) drop wise. The reaction mixture was stirred for about 30 minutes. Subsequently, the crude compound was obtained by adding water to the reaction mixture and extracting in dichloromethane. The organic layer was dried with sodium sulphate and concentrated, purified by silica gel column, using 30% ethyl acetate/hexane as eluent to obtain the title compound.Yield: 11 gSynthetic procedure for Scheme I:

5061-21-2 2-Bromo-4-butanolide 95463, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; RANBAXY LABORATORIES LIMITED; KHERA, Manoj Kumar; SONI, Ajay; SATTIGERI, Jitendra; SATTIGERI, Viswajanani; DAS, Biswajit; CLIFFE, Ian A.; BHATNAGAR, Pradip Kumar; RAUF, Abdul Rehman Abdul; MUSIB, Arpita; SAHA, Subham; YADAV, Neeraj Kumar; AHAMMED, Sabir; REDDY, Ranadheer R.; RAY, Abhijit; SRIVASTAVA, Punit; DASTIDAR, Sunanda Ghosh; WO2012/38942; (2012); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17347-61-4,2,2-Dimethylsuccinicanhydride,as a common compound, the synthetic route is as follows.

A stirring solution of compound 24-1 (55 mg, 0.10 mmol), DMAP (14.8 mg, 0.12 mmol) and 2,2-dimethylsuccinic anhydride (38.7 mg, 0.30 mmol) in dry pyridine (1.0 mL) is heated at 1200C for 4 hours. Another 0.30 mmol of 2,2-dimethylsuccinic anhydride is added and heating at 12O0C is continued for 24 hours. The mixture is cooled down to room temperature and concentrated to dryness. The residue is diluted in ethyl acetate, washed twice with HCl 1 N, water and brine, dried over sodium sulfate and concentrated to dryness. The residue is purified by flash column chromatography on silica gel (methanol/ DCM 0percent to 10percent) to yield the title compound 19-2 as a white solid (48 mg, 71percent). 1H NMR (400 MHz, CDCl3): delta [ppm] 7.71 (m, 2H), 7.50 (m, 1 H), 7.42 (m, 2H), 6.11 (s, 1 H), 4.48 (d x d, 1 H), 3.17 (m, 1 H), 2.90 (d, 1 H), 2.83 (d, 1 H), 2.66 (d, 1 H), 2.55 (d, 1 H), 2.41 (d, 1 H), 2.36 (d, 1 H), 1.95 (m, 3H), 1.76 – 1.16 (m, 26H), 1.13 (s, 3H), 0.97 (s, 3H), 0.87 (s, 3H), 0.83 (s, 3H), 0.79 (s, 3H). LC/MS: m/z = 674.70 (M+H+).

17347-61-4, As the paragraph descriping shows that 17347-61-4 is playing an increasingly important role.

Reference£º
Patent; VIROCHEM PHARMA INC.; WO2009/82819; (2009); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.89364-31-8,Tetrahydrofuran-3-carboxylic acid,as a common compound, the synthetic route is as follows.,89364-31-8

To a solution of tetrahydrofuran-3-carboxylic acid (0.247 mL, 2.58 mmol) in THF (13 mL) at 0 ¡ãC was added slowly lithium aluminium hydride (1 .0 M in THF, 5.2 mL, 5.16 mmol), stirred for 10 minutes then allowed to attain room temperature and stirred for a further 3 hours. The reaction mixture was cooled to 0 ¡ãC and diluted with diethyl ether (15 mL), then treated sequentially with water (0.2 mL), NaOH (15percent solution, 0.2 mL) and water (0.6 mL) and stirred for 30 minutes. The white suspension was then treated with sodium sulfate, stirred for a further 20 minutes, filtered over celite, washed with diethyl ether (2x 20 mL) and concentrated in vacuo to yield 224 mg (85percent) of the title compound as a colourless oil which was carried forward to the next stage without further purification. -NMR Spectrum: deltaEta (500 MHz, CDCI3): 3.90-3.84 (2H, m), 3.78-3.73 (1H, m), 3.66-3.63 (2H, m), 3.61-3.57 (1H, m), 2.51-2.46 (1H, m), 2.08-2.01 (1H, m), 1.69-1.62 (1H, m)

As the paragraph descriping shows that 89364-31-8 is playing an increasingly important role.

Reference£º
Patent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; CHESSARI, Gianni; HOWARD, Steven; BUCK, Ildiko Maria; CONS, Benjamin David; JOHNSON, Christopher Norbert; HOLVEY, Rhian Sara; REES, David Charles; ST. DENIS, Jeffrey David; TAMANINI, Emiliano; GOLDING, Bernard Thomas; HARDCASTLE, Ian Robert; CANO, Celine Florence; MILLER, Duncan Charles; CULLY, Sarah; NOBLE, Martin Edward Maentylae; OSBORNE, James Daniel; PEACH, Joanne; LEWIS, Arwel; HIRST, Kim Louise; WHITTAKER, Benjamin Paul; WATSON, David Wyn; MITCHELL, Dale Robert; (293 pag.)WO2017/55860; (2017); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.63095-51-2,(R)-4-Propyldihydrofuran-2(3H)-one,as a common compound, the synthetic route is as follows.

63095-51-2, Under the protection of nitrogen, brivaracetam intermediate III (128.1g, 1 mol) was dissolved in 1L in methylene chloride. Lower the temperature to 0 C. Add trimethylsilyl iodide (150 ml). The reaction solution at 20-30 C was stirred for 2 hours. Followed by adding hydrochloric acid solution (1M, 800 ml) and sodium thiosulfate aqueous solution (mass percentage of 10%, the quality percent means that the quality of the sodium thiosulfate with the percentage of the total mass of the aqueous solution of sodium thiosulfate, 400 ml. ), The aqueous phase is 1L dichloromethane extraction, the organic phase with saturated salt water washing twice, dried with anhydrous sodium sulfate, filtered, concentrated under reduced pressure to obtain brivaracetam intermediate IV (254.6g), yield 99.5%, purity: 95.6% (GC).

63095-51-2 (R)-4-Propyldihydrofuran-2(3H)-one 10997054, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; Shanghai Bocimed Pharmaceutical Co., Ltd.; Ying, Shuhuan; Pi, Hongjun; Chen, Jian; Zhou, Wei; Zhang, Jueming; (13 pag.)CN106588741; (2017); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.88675-24-5,Tetrahydrofuran-3-amine,as a common compound, the synthetic route is as follows.,88675-24-5

In a 4 mL vial was mixed the 2-chloro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyrimidine (61 mg, 0.25 mmol), tetrahydrofuran-3 -amine (22 mg, 0.25 mmol) and TEA (46 uL, 0.36 mmol) in EtOH (0.3 mL). The reaction was heated to 95 ¡ãC for 2 h before being cooled and concentrated. To the crude residue was added the 2′-bromo-6’H,8’H-spiro[chromane-4,9′-pyrido[3′,2′:4,5]imidazo[2,l-c][l,4]oxazine] (39 mg, 0.10 mmol, Preparation 86), Pd2(dba)3 (9.6 mg, 0.010 mmol), l,3,5,7-Tetramethyl-2,4,8-trioxa-6- phospha-adamantane (6.1 mg, 0.020 mmol) and CS2CO3 (74.8 mg, 0.25 mmol). THF (1 mL) and H20 (0.25 mL) were added, and the reaction was stirred at 60 ¡ãC for 18 h before being cooled to rt and concentrated. The residue was dissolved in 1 : 1 MeOH/DMSO and purified by reverse phase chromatography using a gradient of MeCN (A) and 0.1percent TFA in H20 (B) at a flow rate of 50 mL/min (0- 0.5 min 5percent A, 0.5-8.5 min linear gradient 05-100percent A, 8.7-10.7 min 100percent A, 10.7-11 min linear gradient 100-05percent A) to yield the title compound. (39 mg, 33percent); LC/MS (Table 1, method ai) Rt = 0.61 min; MS 111 ~ 457 (M+H)+. (TNF IC50= B).

As the paragraph descriping shows that 88675-24-5 is playing an increasingly important role.

Reference£º
Patent; ABBVIE INC.; BREINLINGER, Eric, C.; COX, Phil, B.; DAANEN, Jerome; DIETRICH, Justin; DJURIC, Stevan; DOMBROWSKI, Amanda, W.; FRANK, Kristine, E.; FRIEDMAN, Michael, M.; GOMTSYAN, Arthur; LI, Huan-Qui; LONGENECKER, Kenton; OSUMA, Augustine; ROWLEY, Ann, Marie; SCHMIDT, Robert; VASUDEVAN, Anil; WILSON, Noel; (378 pag.)WO2016/168641; (2016); A1;,
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184950-35-4, (Tetrahydrofuran-3-yl)methanamine hydrochloride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5- (1-fluoro-2-naphthylmethoxymethyl) isoxazole-3-carboxylic acid (0.59 g, 1.5 mmol), Tetrahydrofuran-3-ylmethylamine hydrochloride (0.83 g, 6.0 mmol), Triethylamine (0.61 g, 6.0 mmol) And 1-hydroxybenzotriazole (0.06 g, 0.4 mmol) Was added to chloroform (amylen added product) (4 mL) and tetrahydrofuran (4 mL). To the mixture, 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.92 g, 4.8 mmol) was added at room temperature, After stirring overnight, And concentrated under reduced pressure. Dilute hydrochloric acid was added to the residue, And extracted three times with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, After drying with anhydrous sodium sulfate, And concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain the compound represented by the following formula Indicated by N- (tetrahydrofuran-3-ylmethyl) -5- (1-fluoro-2-naphthylmethoxymethyl) isoxazole-3-carboxamide (Hereinafter referred to as present amide compound (258)) 0.07 g was obtained.

184950-35-4, The synthetic route of 184950-35-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; SUMITA, YUSUKE; (264 pag.)JP2015/51963; (2015); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.204512-95-8,(S)-Tetrahydrofuran-3-amine hydrochloride,as a common compound, the synthetic route is as follows.

To a stirred solution of (S)-3-aminotetrahydrofuran hydrochloride (16.0g, 130mmol) in anhydrous THF (250mL) at 0C was added dropwise Et3N (41.5mL, 298mmol) within 20min and stirred another 20min, then a solution of benzyl 2-bromoacetate (29.6g, 130mmol) was added slowly at 0C followed by NaI (1.90g, 13.0mmol). The reaction mixture was stirred at 0C for 30min and then allowed to warm to room temperature and stirred overnight. The solvent was removed under diminished pressure and the residue was treated with water (200mL) and extracted with three 150mL portions of ethyl acetate. The combined organic extracts were dried over Na2SO4 and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (30¡Á6cm). Elution with 3:1 hexanes-ethyl acetate gave 3a as a yellow oil: yield 17.1g (56.1%). 1H NMR (400MHz, CDCl3) delta 7.39-7.30 (m, 5H), 5.16 (s, 2H), 3.91 (dd, J=15.6, 7.6Hz, 1H), 3.80-3.74 (m, 2H), 3.57 (dd, J=9.2, 3.6Hz, 1H), 3.44 (d, J=1.2Hz, 2H), 3.41-3.36 (m, 1H), 2.08-2.00 (m, 1H), 1.76-1.68 (m, 2H); LC-MS (ESI) [M+H]+ m/z 236.2.

204512-95-8, 204512-95-8 (S)-Tetrahydrofuran-3-amine hydrochloride 18664284, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Article; Bai, Xiaoguang; Yang, Zhiheng; Zhu, Mei; Dong, Biao; Zhou, Lei; Zhang, Guoning; Wang, Juxian; Wang, Yucheng; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 30 – 44;,
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165253-29-2, 3-(Bromomethyl)tetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 3-(bromomethyl)tetrahydrofuran (2 g, 12.2 mmol) and AcSK (2.7 g, 24.4 mmol) in DMF (10 mL) was stirred overnight at rt. The mixture was poured into water (50 mL) and extracted with dichloromethane (50 mLx3). The organic extracts were combined, dried over anhydrous sodium sulfate, and concentrated to give crude S-(tetrahydrofuran-3-yl)m ethyl ethanethioate (2.0 g, quantative yield), which was used for next reaction without further purification. The compound was confirmed with LC- MS only: 161.27 (M+H)+, C7Hi202S.

165253-29-2, The synthetic route of 165253-29-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NEUROPORE THERAPIES, INC.; STOCKING, Emily M.; WRASIDLO, Wolfgang J.; (175 pag.)WO2019/199864; (2019); A1;,
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124391-75-9, (S)-(Tetrahydrofuran-3-yl)methanol is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: Preparation of tetrahydrofuran-3-ylmethyl 4-methylbenzenesulfonate To a stirred solution of tetrahydro-3-furanmethanol (500 mg, 4.90 mmol) in DCM (5 mL) was added Et3N (892 mg, 8.81 mmol) and DMAP (60 mg, 0.49 mmol). Then to the mixture was added a solution of 4-methylbenzenesulfonyl chloride (1.4 g, 7.34 mmol) in DCM (5 mL) dropwise. After being stirred at 15 oC for 16 hrs, the resulting mixture was diluted with DCM (50 mL), washed with H2O (20 mL), 2 N HCl (20 mL) and brine (10 mL), then dried over anhydrous Na2SO4 and concentrated in vacuo to give tetrahydrofuran-3-ylmethyl 4- methylbenzenesulfonate (1.1 g) as a colorless oil, which was used in the next step directly without further purification.

124391-75-9, 124391-75-9 (S)-(Tetrahydrofuran-3-yl)methanol 40784875, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; JIANG, Min; WANG, Jianhua; WANG, Min; WANG, Yongguang; YANG, Song; (319 pag.)WO2016/177655; (2016); A1;,
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16874-33-2, Tetrahydrofuran-2-carboxylic acid is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of TETRAHYDROFURAN-2-CARBOXYLIC acid (20 g, 172. 2356 MMOL) in anhydrous ethanol (100 mL) was added concentrated sulfuric acid (0. 46 mL). The resulting mixture was stirred at reflux for 16 hours and then allowed to cool to ambient temperature. To this was added water (100 mL) and extracted with diethyl ether (3×100 mL). The combined organic extracts were washed with saturated aqueous sodium bicarbonate (2X50 mL), saturated aqueous sodium chloride (100 ML), dried (anhydrous magnesium sulfate), filtered and concentrated in vacuo to afford the pure product as a colorless liquid (22. 5964 g, 91 %). LRMS (m/z) : 145 (M+H) +. ‘H NMR (CDCI3, 300 MHz) 4. 38 (1H, dd, J= 4. 9, 8. 1 HZ), 4. 14 (2H, q, J= 7. 2 Hz), 3. 99-3. 92 (1 H, m), 3. 88-3. 81 (1 H, M), 2. 24-2. 12 (1 H, M), 2. 00-1. 79 (3H, m), 1. 22 (3H, t, J=7. 2Hz)., 16874-33-2

16874-33-2 Tetrahydrofuran-2-carboxylic acid 86079, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; PFIZER INC.; WO2004/92145; (2004); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem