Heterocyclic Building Blocks-Tetrahydrofuran

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;,
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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.

General procedure: To a stirred mixture of thiols 12a-12k (100 mmol) and K2CO3(27.64 g, 200 mmol) in DMF (120 mL) at room temperaturewas added alpha-bromobutyrolactone (10, 14.85 g, 90 mmol), andthe resulting mixture was stirred at room temperature until thecompletion of reaction as indicated by TLC analysis (typicallywithin 12 h).The reaction mixture was poured into ice-water (400 mL),and the mixture thus obtained was extracted with CH2Cl2 (3 ¡Á100 mL). The combined extracts were washed successively with10% aqueous Na2CO3 (2 ¡Á 100 mL) and 5% brine (3 ¡Á 100 mL),dried over anhydrous Na2SO4 and evaporated on a rotary evaporator to aord a residue, which was purifed by columnchromatography to yield 13a-13k after trituration withEtOAc/n-hexane if the product was a solid.

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

Reference£º
Article; Zhang, Xiansheng; Wu, Jingwei; Liu, Yuqiang; Xie, Yafei; Liu, Changying; Wang, Jianwu; Zhao, Guilong; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 192; 7; (2017); p. 799 – 811;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.118399-28-3,(R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

0101 (5.04 g, 21.4 mmol) was added into a solution of methanamine (31.06g, 1 mol) in ethanol (100 ml) and stirred for 15 m, during this period 0101 was dissolved gradually and then new solid appeared. The solvent was evaporated under reduced pressure to obtain 0102 (5.016 g, 88%) as a white solid which was used in the next step reaction without further purification. LCMS: 267 [M+l]+; 1H NMR (DMSO-J6): delta 2.18 (dd, IH, J1 = 8.4 Hz5 J2 = 14.1 Hz), 2.31 (dd, IH, J1 = 6.3 Hz5 J2 = 14.4 Hz), 2.54 (d, 3H, J= 5.1 Hz), 3.33 (m, IH), 3.82 (m, IH), 4.703 (m, IH), 5.00 (s, 2H), 6.98 (d, IH, J= 8.4 Hz), 7.35 (m, 5H), 7.68 (m, IH).

118399-28-3 (R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate 697924, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; CURIS, INC.; WO2009/36051; (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.2399-48-6,(Tetrahydrofuran-2-yl)methyl acrylate,as a common compound, the synthetic route is as follows.

To the 20 mL reaction tube was added 112 mg (0.5 mmol) of compound dibenzoylmethane, 7 mg (0.025 mmol) of K2CO3, 147 muL (1 mmol) of tetrahydrofurfural acrylate and 0.5 mL of tetrahydrofurfuryl alcohol at a temperature of 85 C The reaction was stirred for 24 hours and cooled to room temperature (18-25 C) and transferred to a small flask of 10 mL. The solvent was distilled off under reduced pressure and then passed through a column of neutral alumina. The developing solvent used was petroleum ether: ethyl acetate= 13: 1 to 4: 1 to give compound III-16 126 mg in 91% yield

The synthetic route of 2399-48-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Southwest University; Cai Guixin; Wen Jing; (13 pag.)CN105061125; (2017); B;,
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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.

To (2-bromo-6,7-dihydrothia.zolo[5 ,4-c]pyridin-5(4H)-yl)( 1 H-indol-2-yl)methanone (0.030 g, 0.083 mmol) was added tetrahydrofuran-3-amine (0.250 mL, 2.90 mmol). The mixture was stirred at 60¡ãC for 96 hours. The mixture was then purified directly by basic reverse phase HPLC to give the desired product (0.0023 g, 7percent yield)Rt (Method A) 3.22 mins, m/z 369 [M+H].

The synthetic route of 88675-24-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AICURIS GMBH & CO. KG; DONALD, Alastair; URBAN, Andreas; BONSMANN, Susanne; WEGERT, Anita; GREMMEN, Christiaan; SPRINGER, Jasper; (376 pag.)WO2019/86141; (2019); A1;,
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5061-21-2, 2-Bromo-4-butanolide is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Starting with a solution of the appropriate amine (2.5 equiv) in dry MeCN or DCM, anhydrous K2CO3 (1 or 2 equiv) and tetrabutylammonium bromide (TBAB, 0.1 equiv) were added and the reaction mixture was stirred at room temp for 30 min. Subsequently, the reaction mixture was cooled down to 0 C and a solution of 3-bromo-dihydrofuran-2(3H)-one (2.5 equiv) in dry solvent (MeCN or DCM) was added. Stirring was continued at 0 C for 1 h and then at room temp for 3-50 h. The resultant mixture was filtered and the solvent evaporated. The oily residue was dissolved in solution of EtOH or MeOH with Et2O and acidified to pH 2-3 with saturated HCl solution in EtOH. After 2-7 days of at 5 C a hydrochloride salt precipitated. The salt was then purified by recrystallization from the appropriate solvent (EtOH or MeOH).

The synthetic route of 5061-21-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wieckowski, Krzysztof; Bytnar, Justyna; Bajda, Marek; Malawska, Barbara; Salat, Kinga; Filipek, Barbara; Stables, James P.; Bioorganic and medicinal chemistry; vol. 20; 21; (2012); p. 6533 – 6544,12;; ; Article; Wi?ckowski, Krzysztof; Sa?at, Kinga; Bytnar, Justyna; Bajda, Marek; Filipek, Barbara; Stables, James P.; Malawska, Barbara; Bioorganic and Medicinal Chemistry; vol. 20; 21; (2012); p. 6533 – 6544;,
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Tetrahydrofuran | (CH2)3CH2O – PubChem

88675-24-5, Tetrahydrofuran-3-amine is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Compound TDI01113-4 (200 mg, 0.52 mmol) and tetrahydrofuran-3-amine (54.6 mg, 0.62 mmol) were dissolvedin N,N-dimethylformamide (10 mL), HATU (236 mg, 0.62 mmol) and diisopropylethylamine (268 mg, 2.08 mmol) wereadded, and the reaction was performed at room temperature overnight. Thin layer chromatography (dichloromethane/methanol =10:1) indicated the reaction was complete. Water (60 mL) was slowly added to the reaction solution, a largeamount of solid precipitated and was filtered after being stirred for 30 minutes. The solid was purified by high-performanceliquid chromatography to afford compound TDI01113 (56.2 mg, yellow solid, yield: 23.7percent).1H NMR (400 MHz, DMSO-d6) delta 13.05 (s, 1H), 9.67 (s, 1H), 8.93 (s, 1H), 8.90 (d, J = 6.4 Hz, 1H), 8.42 (dd, J = 8.4, 1.2Hz, 1H), 8.39 (d, J = 6.0 Hz, 1H), 8.23 (s, 1H), 8.18 (s, 1H), 8.10 (s, 1H), 8.06 (d, J = 8.4 Hz, 1H), 7.59 (s, 2H), 6.71 (d,J = 6.0 Hz, 1H), 4.51 – 4.45 (m, 1H), 3.91 – 3.85 (m, 2H), 3.77 – 3.71 (m, 1H), 3.66 – 3.63 (m, 1H), 2.24 – 2.15 (m, 1H),1.99 – 1.92 (m, 1H). MS m/z (ESI): 457.0 [M+H].

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

Reference£º
Patent; Beijing Tide Pharmaceutical Co., Ltd.; Zhao, Yanping; Wang, Hongjun; Li, Gong; Jiang, Yuanyuan; Li, Xiang; Zhou, Liying; Liu, Yanan; (235 pag.)EP3421465; (2019); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.57595-23-0,Methyl 4-oxotetrahydrofuran-3-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of metliyl-4-oxo-tetrahydrofuro-3-carboxylate (1.18 g, 8,19 mmol) in ethanol (5 mL), l-(l,3-benzothiazol-2~yl)methanamine hydrochloride (1.73 g, 8.60 ramol), triethylamine (1.20 mL, 8.60 mmol) and acetic acid (47 muL, 0.819 mmol) were added and the reaction mixture was heated to reflux for 6 hr, cooled to ambient temperature and concentrated in vacuo. The resultant residue was partitioned between EtOAc (10 mL) and H2O (5 mL) and the organic layer was washed with KHSO4 (1 X 5 mL), NaHCO3 (1 X 5 mL) brine (1 X 5 mL), dried over MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography 10,15% EtOAc/hexanes on SiO2 (40 S+ column) afforded 610 mg of an orange foam: * H NMR (500 MHz, CDCl3) delta 3.73 (s, 3 H), 4.67 (d, 2 H, J- 6.8 Hz), 4.80 (s, 4 H), 7.40 (t, 1 H, J= 7.5Hz), 7.50 (I, 1 H, J= 12 Hz), 7.87 (d, 1 H, J= 8.0 Hz), 7.99 (d, 1 H, J= 8.2 Hz).

As the paragraph descriping shows that 57595-23-0 is playing an increasingly important role.

Reference£º
Patent; MERCK & CO., INC.; WO2009/108496; (2009); 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.165253-29-2,3-(Bromomethyl)tetrahydrofuran,as a common compound, the synthetic route is as follows.

Potassium carbonate (60.1 mg) was added to a mixture of 2-(4-chlorophenyl)-5-(4-hydroxy-3-methoxyphenyl)furo[3,2-c]pyridin-4(5H)-one (80 mg), 3-(bromomethyl)tetrahydrofuran (53.8 mg) and DMF (1.5 mL) at room temperature, and the mixture was stirred at 80¡ãC for 2 hr. To the resulting mixture was dropwise added brine, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the solid was recrystallized from ethanol to give the title compound (35.8 mg) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) delta 1.70-1.87 (1H, m), 2.02-2.21 (1H, m), 2.67-2.97 (1H, m), 3.71-3.84 (2H, m), 3.85-3.89 (3H, m), 3.90-4.05 (4H, m), 6.64 (1H, d, J = 7.5 Hz), 6.81-7.03 (3H, m), 7.16-7.33 (2H, m), 7.42 (2H, d, J = 8.4 Hz), 7.71 (2H, d, J = 8.5 Hz). MS (ESI+):[M+H]+ 452.1.

As the paragraph descriping shows that 165253-29-2 is playing an increasingly important role.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; KASAI, Shizuo; IGAWA, Hideyuki; TAKAHASHI, Masashi; KINA, Asato; EP2848622; (2015); A1;,
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Tetrahydrofuran | (CH2)3CH2O – PubChem

453-20-3, 3-Hydroxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 36: (2S)-tetrahydrofuran-3-yl 2-((tert-butoxycarbonyl)amino)butanoate A mixture of (S)-2-((tert-butoxycarbonyl)amino)butanoic acid (2.5 g, 12.3 mmol), diisopropylethylamine (3.18 g, 4.3 mL, 24.6 mmol), 1-hydroxybenzotriazole hydrate (2.26g, 14.76 mmol), EDC (2.83 g, 14.76 mmol), and tetrahydrofuran-3-ol (10.84 g, 9.97 mL, 123 mmol) in DMF (20 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate (50 mL) and saturated NaHCO3 (50 mL). The organic phase was washed with 1M hydrochloric acid (50 mL), water (50 mL) and brine (50 mL). The organic phase was dried and evporated to give the title compound (3.07 g, 11.23 mmol, 91 % yield), as a colourless oil.1H NMR (400 MHz, DMSO-d6) delta ppm 5.30-5.34 (m, 1H), 5.00-5.04 (m, 1H), 4.16-4.22 (m,1H), 3.92-3.94 (m, 1H), 2.12-2.22 (m, 1H). 1.93-2.03 (m, 1H), 1.78-1.84 (m, 1H), 1.60-1.69 (m, 1H), 1.43 (s, 9H), 0.92 (t, J = 12.0 Hz, 3H).

As the paragraph descriping shows that 453-20-3 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BIT, Rino Antonio; BROWN, John Alexander; HUMPHREYS, Philip G.; JONES, Katherine Louise; (240 pag.)WO2016/146738; (2016); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem