Heterocyclic Building Blocks-Tetrahydrofuran

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

5-fluoro-4-[4-methyl-5-oxo-3-(propan-2-yl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]-2-{[(2S)-4-methylpentan-2-yl]oxy}benzoic acid (Intermediate 82, 150 mg, 395 muiotaetaomicronIota) and tetrahydrofuran-3-amine (44.0 mg, 505 muiotaetaomicronIota) were dissolved in dichloromethane (20 mL). Triethylamine (167 muIota_, 1 .2 mmol) was added, followed by HATU (190 mg, 499 muiotaetaomicronIota). The mixture was stirred at room temperature overnight. The solvent was removed and the mixture was purified using preparative TLC to yield 66mg of desired product (37percent yield).

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Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; THE GENERAL HOSPITAL CORPORATION; GRADL, Stefan, Nikolaus; NGUYEN, Duy; EIS, Knut; GUeNTHER, Judith; STELLFELD, Timo; JANZER, Andreas; CHRISTIAN, Sven; MUELLER, Thomas; EL SHEIKH, Sherif; ZHOU, Han, Jie; ZHAO, Changjia; SYKES, David, B; FERRARA, Steven, James; LIU, Kery; KROeBER, Michael; MERZ, Claudia; NIEHUES, Michael; SCHAeFER, Martina; ZIMMERMANN, Katja; NISING, Carl, Friedrich; (509 pag.)WO2018/77923; (2018); A1;,
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204512-95-8, (S)-Tetrahydrofuran-3-amine hydrochloride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a dried reaction flask, 2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-carboxylic acid (0.421 g, 1.0 mmol), (S)-tetrahydrofuran-3-amine hydrochloride (0.161 g, 1.3 mmol), DIEA (0.26 mL, 1.5 mmol), and HATU (0.418 g, 1.1 mmol) were added to a mixed solvent of DMF (4 mL) and dichloromethane (8 mL). The mixture was stirred at room temperature for 2 hr 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 (0.363 g) 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).

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

Reference£º
Patent; Huang, Zhenhua; Wang, Jinyuan; Zhang, Dedong; US2013/289029; (2013); A1;,
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453-20-3, 3-Hydroxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 21a (0.6g, 6.81mmol) and TEA (1.05g, 8.17mmol) in THF was added methanesulfonyl chloride (0.86g, 7.50mmol) cooled by ice-bath. The mixture was stirred over weekend and then evaporated. The residue was dissolved in EtOAc and washed with aq. NaHCO3. The organic phase was dried over Na2SO4 and 15 concentrated to provide 21b (1.Ig, 97% yield).

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

Reference£º
Patent; XCOVERY, INC.; WO2008/88881; (2008); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.64001-06-5,4-((Tetrahydrofuran-2-yl)oxy)butan-1-ol,as a common compound, the synthetic route is as follows.

Example 5 10 g of a mixture of 2-(4-hydroxybutoxy)tetrahydrofuran of the formula IIc (83%) and 1,4-bis(2-tetrahydrofuranyloxy)butane (17%) obtained as described in section (b) of Example 1 were hydrogenated at 100 C. and 150 bar in the presence of 1 g of a palladium catalyst (10% of Pd on activated carbon) for 10 hours.

64001-06-5 4-((Tetrahydrofuran-2-yl)oxy)butan-1-ol 11744922, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; BASF Aktiengesellschaft; US5008408; (1991); A;,
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87392-05-0, (R)-(+)-2-Tetrahydrofuroic acid is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(2R)-tetrahydrofuran-2-carboxylic acid (2 g, 17.22 mmol) was dissolved in 20 mL of THF under argon and the flask was cooled in an ice bath, BH3.SMe2 (2M solution in THF, 10 mL, 20.0 mmol) was added to the reaction solution over 10 minutes. The ice bath was removed and the solution was stirred for 1 h at room temperature. The solution was again cooled in an ice bath and methanol slowly added until no gas evolution was observed. The solution was concentrated in vacuum to give the desired product as oil (m = 1 g, 60 %). 1H NMR (300 MHz, CDCI3) delta 1 .55- 1 .70 (m, 1 H), 1 .72-1 .98 (m, 3H), 3.35-4.00 (m, 6H).

87392-05-0 (R)-(+)-2-Tetrahydrofuroic acid 2734707, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; UNIVERSITE DE LILLE 2 DROIT ET SANTE; INSTITUT PASTEUR DE LILLE; INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE); CHARTON, Julie; DEPREZ, Benoit; LEROUX, Florence; STAELS, Bart; MUHR-TAILLEUX, Anne; HENNUYER, Nathalie; LESTAVEL, Sophie; PICON, Sylvain; AKNIN, Karen; BOULAHJAR, Rajaa; DUBANCHET, Barbara; (234 pag.)WO2016/16238; (2016); A1;,
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453-20-3, 3-Hydroxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 1 L flask, 3-tetrahydrofuran (3-OH-THF, 60.6 g, 0.68 mol, 1 equ.) was charged, followed by DCM (620 mL) and TEMPO(1.08 g, 0.0069 mol, 0.01 equ.) The solution was cooled to -5 ¡ãC. To which TCCA (159.6 g, 0.68 mol, 1 equ.) was added in portions controlling the tern- perature around -5 ¡ãC to 0 ¡ãC. The resulting mixture was allowed to warm to rt and monitored by GC-MS, Reaction was finished in 1 h to give 95percent yield (GC areapercent).

453-20-3 3-Hydroxytetrahydrofuran 9960, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL TRADING (SHANGHAI) CO., LTD.; XING, Lidong; DONG, Weitong; LU, Jun; SCHOLZ, Ulrich; YAN, Jun; YANG, Jinsong; WO2014/139080; (2014); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.453-20-3,3-Hydroxytetrahydrofuran,as a common compound, the synthetic route is as follows.

3-hydroxytetrahydrofuran (869.00 jiL, 10.56 mmol) was diluted in THF (33.5 mL). Then, the solution was cooled to 0 C and LiHMDS (10.00 mL, 10.56 mmol) was added. After 30 mi 2-fluoro-3-nitropyridine (1.50 g, 10.56 mmol) was quickly added and the reaction mixture was stirred overnight allowing the temperature to reach rt. Thereaction mixture was mixed with another batch (from 100 mg of 2-fluoro-3- nitropyridine) and partitioned between water and EtOAc. The organic layer was separated, dried over MgSO4, filtered and concentrated to afford 2.03 g of intermediate 54 (91% yield) which was directly engaged in the next steps without any further treatment.

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

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (476 pag.)WO2017/125534; (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.873063-62-8,(R)-3-Iodotetrahydrofuran,as a common compound, the synthetic route is as follows.

[0388] N-(3′-Fluoro-5,6′-dimethyl-2,2′-bipyridin-4-yl)-2H-pyrazolo[4,3-b]pyridin-7-amine (43 mg, 0.129 mmol) was dissolved in DMF (2 mL), cooled to 0C and sodium hydride (4.75 mg, 60%), 0.129 mmol) was added. The reaction mixture was stirred for 5 minutes and (R)-3-iodotetrahydrofuran (25.5 mg, 0.129 mmol) was added and further stirred for 5 minutes at room temperature and then heated in a microwave at 65C for 40 minutes. The reaction mixture was then cooled, concentrated in vacuo to give a residue which was combined with MeOH and filtered. The filtrate was purified by preparative HPLC using a Sunfire Prep 5muiotaeta CI 8, 75 X 30 mm column 5 muiotaeta CI 8, 75 X 30 mm column eluting with a gradient of 5-30% acetonitrile (containing 0.035% TFA) in water (containing 0.05% TFA) to give the title compounds as TFA salts: (S)-N-(3′-fluoro-5,6′-dimethyl-2,2′-bipyridin-4-yl)- l-(tetrahydrofuran-3-yl)-lH-pyrazolo[4,3-b]pyridin-7-amine 1H NMR (400 MHz,CHLOROFORM- ) delta ppm 1.27 – 1.42 (m, 1 H) 2.36 – 2.39 (m, 4 H) 2.39 – 2.51 (m, 2 H) 2.55 (s, 3 H) 3.80 – 3.89 (m, 1 H) 4.01 (dd, J=9.85, 7.33 Hz, 1 H) 4.11 – 4.22 (m, 2 H) 7.01 (d, J=3.54 Hz, 1 H) 7.14 (dd, J=8.46, 3.41 Hz, 1 H) 7.31 – 7.44 (m, 2 H) 8.25 (s, 1 H) 8.41 (br. s., 1 H), MS [M+H] found 405.4; and (S)-N-(3*-fluoro-5,6*-dimethyl-2,2,-bipyridin-4-yl)- l-(tetrahydrofuran-3-yl)-lH-pyrazolo[4,3-b]pyridin-7-amine 1H NMR (400 MHz,CHLOROFORM-;/) delta ppm 2.44 (s, 3 H) 2.46 – 2.56 (m, 1 H) 2.57 – 2.70 (m, 4 H) 4.04 (td, J=8.59, 5.56 Hz, 1 H) 4.18 – 4.31 (m, 3 H) 5.22 – 5.33 (m, 1 H) 7.02 (d, J=5.05 Hz, 1 H) 7.13 – 7.23 (m, 2 H) 7.43 (dd, J=10.48, 8.46 Hz, 1 H) 8.13 (d, J=1.26 Hz, 1 H) 8.26 (s, 1 H) 8.41 (d, J=5.05 Hz, 1 H) 8.62 (s, 1 H), MS [M+H] found 405.4.

The synthetic route of 873063-62-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KWOK, Lily; LARSON, John David; SABAT, Mark; WO2011/146287; (2011); 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- (2,5-difluorobenzyloxymethyl) isoxazole-3-carboxylic acid (0.54 g, 2.0 mmol), Tetrahydrofuran-3-ylmethylamine hydrochloride (0.41 g, 3.0 mmol), Triethylamine (0.30 g, 3.0 mmol) And 1 – hydroxybenzotriazole (0.03 g, 0.2 mmol) Was added to chloroform (amylen added product) (5 mL). To the mixture, 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.46 g, 2.4 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 hydrogen carbonate solution , Washed with saturated brine, After drying with anhydrous sodium sulfate, And concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, The following equation Indicated by N- (tetrahydrofuran-3-ylmethyl) -5- (2,5-difluorobenzyloxymethyl) isoxazole-3-carboxamide (Hereinafter referred to as the present amide compound (259)) 0.17 g was obtained.

As the paragraph descriping shows that 184950-35-4 is playing an increasingly important role.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; SUMITA, YUSUKE; (264 pag.)JP2015/51963; (2015); A;,
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42417-39-0, 3-Aminodihydrofuran-2(3H)-one hydrochloride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of 4-(5-(substituted phenyl)-1,2,4-oxadiazol-3-yl)benzaldehyde (0.53mmol)in 10mL DCM was added methyl glycinate hydrochloride (0.80mmol), acetic acid (2.12mmol), and N,N-diisopropylethylamine (0.80mmol), and 10mL MeOH. After the reaction was stirred for 3h, sodium cyanoborohydride (0.53mmol) was added. The reaction mixture was quenched with saturated aqueous NaHCO3 solution and extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, then filtered and concentrated. The residue was purified by silica gel flash column chromatography (DCM:MeOH=20:1) to afford compound 15-1a?15-3n (except for 15-1l).

The synthetic route of 42417-39-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Liu, Tianqi; Jin, Jing; Chen, Yonghui; Xi, Qiumu; Hu, Jinping; Jia, Wenqiang; Chen, Xiaoguang; Li, Yan; Wang, Xiaojian; Yin, Dali; Bioorganic Chemistry; vol. 82; (2019); p. 41 – 57;,
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