Category: Tetrahydrofurans

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

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;,
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.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.204512-95-8,(S)-Tetrahydrofuran-3-amine hydrochloride,as a common compound, the synthetic route is as follows.

In a dried reaction flask,2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-carboxyli c acid (0.421g, 1.0mmol), (S)-tetrahydrofuran-3-amine hydrochloride (0.161g, 1.3mmol), DIEA (0.26mL, 1.5mmol), and HATU (0.418g, 1.1mmol) were added to a mixed solvent of DMF (4mL) and dichloromethane (8mL). The mixture was stirred at room temperature for 2hr and was concentrated under reduced pressure. Water was added to the residue. The mixture was filtered to produce a crude yellow solid, which was washed with methanol to produce a purified product (0.363g) in 74.1 % yield. Molecular formula: C27H28ClN5O2; mass spectrum (M+H): 490.2 1H-NMR(DMSO-d6, 400 MHz): delta 8.63 (1H, d), 8.49 (1H, d), 7.94 (1H, d), 7.71 (1H, d), 7.44 (1H, d), 7.22 (1H, dd), 5.02 (1H, dd), 4.62-4.41 (1H, m), 3.94-3.79 (2H, m), 3.78-3.57 (3H, m), 3.26-3.16 (1H, m), 3.14-2.99 (1H, m), 2.37-1.87 (5H, m), 1.79-1.65 (1H, m), 1.58-1.16 (7H, m).

The synthetic route of 204512-95-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; KBP Biosciences Co., Ltd.; HUANG, Zhenhua; WANG, Jinyuan; ZHANG, Dedong; EP2607363; (2013); 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.88675-24-5,Tetrahydrofuran-3-amine,as a common compound, the synthetic route is as follows.

Compound VIII-5 (400 mg, 0.90 mmol) and 3-aminotetrahydrofuran (IX-8) (48 mg, 1.35 mmol) were dissolved in sec-butanol (3 mL), and the mixture was heated to 125 C for 12 h, until TLC (two Methyl chloride: methanol = 25:1) The starting material VIII-5 was reacted completely, the reaction solution was cooled to room temperature, and the solvent was evaporated to dryness under reduced pressure.200:1 to 50:1), obtained as a white solid, 220 mg, yield: 54.2%

#N/A

Reference£º
Patent; China Pharmaceutical University; Xu Yungen; Ji Dezhong; Zhang Lingzhi; Zhu Qihua; Bai Ying; Wu Yaoyao; (41 pag.)CN109608444; (2019); 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.138498-97-2,2-(Tetrahydrofuran-3-yl)acetic acid,as a common compound, the synthetic route is as follows.

To a solution of 1-iodobutane (12.4 g, 67.9 mmol) in acetonitrile (100 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (9.36 g, 61.1 mmol), followed by (tetrahydro-furan-3-yl)-acetic acid (8.0 g, 61.1 mmol) at 0 C. The resulting mixture was stirred at 25 C. for 12 h and poured into water (100 mL). The mixture was extracted with ethyl acetate (2*100 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude butyl 2-tetrahydrofuran-3-ylacetate (11.0 g, 96%) as a yellow oil, used as is in the next step.

As the paragraph descriping shows that 138498-97-2 is playing an increasingly important role.

Reference£º
Patent; Genentech, Inc.; Patel, Snahel; Hamilton, Gregory; (73 pag.)US2018/170927; (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.97-99-4,(Tetrahydrofuran-2-yl)methanol,as a common compound, the synthetic route is as follows.

Example 77Preparation of 2-(T4-fluorophenvD(‘((‘RVtetrahvdrofiotaiotaran-2-yl)methoxy>)methyl)-N-(5 – methyl- lH-pyrazol-3-yl)pyrrolorK2-firi,2,41triazin-4-amineC[00392] To a suspension of 2-(bromo(4-fiuorophenyl)methyl)-N-(5 -methyl- 1 H- pyrazol-3-yl)pyrrolo[l,2-fJ[l,2,4]triazin-4-amine from Example 69, Step A (0.069 g, 0.17 mmol) in DCM (2 mL) were added (R)-(tetrahydrofuran-2-yl)methanol (0.05 mL, 0.51 mmol), 2,6-di-tert-butylpyridine (0.077 mL, 0.34 mmol) silver trifluoromethansulfonate (0.065 g, 0.26 mmol). The solution was stirred for 10 min, filtered rinsing with MeOH, and the filtrate was concentrated. The residue was purified by preparative HPLC (Phenomenex C- 18 reverse phase column, eluted with gradient of solvent B = 0.05% HOAC/CH3CN and solvent A = 0.05% HOAc/H2O) to afford 2-((4-fluorophenyl)(((R)-tetrahydrofuran-2-yl)methoxy)methyl)-N-(5-methyl- lH-pyrazol-3-yl)pyrrolo[l,2-fJ[l,2,4]triazin-4-amine (4.6 mg, 6 % yield). ). 1H NMR (300 MHz, DMSO-J6) delta 1.66-1.91 (m, 4H), 2.26 (s, 3H), 3.4-3.7 (m, 4H)5 4.02 (m, IH), 5.35 (s, IH), 6.5-6.7 (m, 2H), 7.15-7.2 (m, 3H), 7.56 (t, 2H), 7.72 (s, IH), 10.6 (s, IH), 12.2 (bs, IH); LC-MS (ESI) m/z 423 (M + H)+.

The synthetic route of 97-99-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AMBIT BIOSCIENCES CORPORATION; ABRAHAM, Sunny; CHAO, Qi; HADD. Michael, J.; HOLLADAY, Mark, W.; LIU, Gang; NAMBU, Mitchell, D.; SETTI, Eduardo; WO2010/2472; (2010); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

915095-89-5, (S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Add Compound C-2 (10 g, 27.2 mmol) to a 250 mL three-necked flaskAnd 70mL of tetrahydrofuran, stir and dissolve.The resulting solution is cooled to -70 to -80 C,Slowly add n-butyllithium solution (2.5M THF solution) to the cooled solution.12.5 mL, 1.15 eq), and stirred at -70 to -80 C for 1 hour.Further, a solution of the compound B in tetrahydrofuran (8.5 g of B in 30 mL of tetrahydrofuran, 31.3 mmol, 1.15 eq) was added dropwise to the reaction mixture.The mixture was stirred at -70 to -80 C for 2 hours. The reaction solution is heated to -10 to 0 C.The reaction solution was diluted with a saturated aqueous solution of NH 4Cl (20 mL).Add ethyl acetate(100 mL ¡Á 2) The reaction quenching solution was extracted twice, and the ethyl acetate layer was combined.The organic layer was washed with saturated brine (100 mL).The organic layer was concentrated to dryness under reduced pressure at 40 to 50 C.The resulting solid was recrystallized from ethyl acetate and n-hexane.Having 11.4g of compoundD-2, yield 88.4%.

As the paragraph descriping shows that 915095-89-5 is playing an increasingly important role.

Reference£º
Patent; Zhejiang Hongyuan Pharmaceutical Co., Ltd.; Wang Haibo; Mei Guangyao; Jin Hui; Zhang Wei; Liu Xuesheng; Lin Wenjing; Wang Kaiming; (20 pag.)CN108675976; (2018); A;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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

(Z)-2-Fluoro-2-nonoic acid (0.97 g, 5.5 mmol) and tetrahydrofuran-3-ylmethylamine hydrochloride (0.92 g, 6.7 mmol) were added to N,N-dimethylformamide (15 mL). To the mixture solution was added triethylamine (1.45 g, 14.3 mmol) under ice cooling, then, benzotriazol-1-yloxy-tris(dimethylamino)phosphonium salt (3.20 g, 7.2 mmol) was added. The mixture was stirred under ice cooling for 1 hour, then stirred at room temperature for 12 hours, and thereafter, the reaction solution was added to a mixture of 20 mL of 5% of hydrochloric acid and 50 mL of ice water, and the mixture was extracted twice with 100 mL of ethyl acetate. The ethyl acetate layers were combined, and washed with 50 mL of a saturated sodium bicarbonate solution, followed by 50 mL of a saturated salt solution. Thereafter, the organic layer was dried over magnesium sulfate and was concentrated under reduced pressure conditions, and the residue was applied to a silica gel column chromatography, to obtain 0.73 g of (Z)-N-(tetrahydrofuran-3-ylmethyl)-2-fluoro-2-nonenamide (hereinafter, described as Compound (7) of the present invention) represented by the following formula.1H-NMR (CDCl3, TMS) delta (ppm) : 0.88 (t, 3H), 1.24-1.36 (m, 6H), 1.40-1.47 (m, 2H), 1.61-1.68 (m, 1H), 2.02-2.10 (m, 1H), 2.20 (ddd, 2H), 2.48-2.58 (m, 1H), 3.32-3.42 (m, 2H), 3.56 (dd, 1H), 3.75 (dd, 1H), 3.83 (dd, 1H), 3.90 (td, 1H), 6.10 (dt, 1H), 6.35 (br s, 1H)

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; IHARA, Hideki; AWANO, Tomotsugu; OHSHITA, Jun; MATSUO, Noritada; EP2813493; (2014); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

17347-61-4, 2,2-Dimethylsuccinicanhydride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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 120¡ã C. for 4 hours.Another 0.30 mmol of 2,2-dimethylsuccinic anhydride is added and heating at 120¡ã C. 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 1N, 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, 1H), 7.42 (m, 2H), 6.11 (s, 1H), 4.48 (d*d, 1H), 3.17 (m, 1H), 2.90 (d, 1H), 2.83 (d, 1H), 2.66 (d, 1H), 2.55 (d, 1H), 2.41 (d, 1H), 2.36 (d, 1H), 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*).

The synthetic route of 17347-61-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Moinet, Christophe; Halab, Liliane; Turcotte, Nathalie; Bubenik, Monica; Courchesne, Marc; Poisson, Carl; Pereira, Oswy Z.; Nguyen-Ba, Paul; Liu, Bingcan; Chauret, Nathalie; Cadilhac, Caroline; Kong, Laval Chan Chun; US2011/77227; (2011); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem