Heterocyclic Building Blocks-Tetrahydrofuran

87219-29-2, (S)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

87219-29-2, In a 500 ml round-bottomed flask phenylmethyl [(3S)-5-oxotetrahydro-3-furanyl]carbamate (4.3 g, 18.28 mmol, available from Sigma -Aldrich No. 419249) was dissolved in water (100 ml) and acetone (100 ml) and to this solution CS2CO3 (10.72 g, 32.9 mmol) was added and the reaction left under stirring at room temperature for 5 hours. The solution was then transferred into a separatory funnel and washed with EtOAc (2 x 50 ml). The aqueous phase was then acidified to pH = 2 by the addition of a 2 M HCl aqueous solution and then extracted with EtOAc (5 x 100 mis). The organic phase was dried (Na2SO4) and solvent removed under reduced pressure to give the title compound Dl (3.78 g) as a white solid. MS: (ES/+) m/z: 254 (M+l). C12H15NO5 requires 253. 1H NMR (400 MHz, DMSO-J6) delta (ppm): 12.11 (bs, 1 H), 7.41-7.07 (m, 5 H), 5.17-4.92 (m, 2 H), 3.95-3.62 (m, 1 H), 3.42- 3.22 (m, 2 H), 2.55-2.40 (m, 1 H), 2.34-2.23 (m, 1 H)

The synthetic route of 87219-29-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; ALVARO, Giuseppe; AMANTINI, David; CASTIGLIONI, Emiliano; DI FABIO, Romano; PAVONE, Francesca; WO2010/63662; (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.88675-24-5,Tetrahydrofuran-3-amine,as a common compound, the synthetic route is as follows.,88675-24-5

A mixture of (6-(4-((6-chloropyridazin-3-yl)methoxy)-2-oxopyridin-l (2H)-yl)-7,8- dihydronaphthalen-2-yl)methyl methanesulfonate (350 mg, 0.739 mmol), tetrahydrofuran-3- amine (77 mg, 0.886 mmol) and K2CO3 (306 mg, 2.216 mmol) in N, N-dimethylformamide (DMF) (15 mL) was stirred at 80 ¡ãC for 6 hr, then solvent was removed to give the residue which was purified by prep HPLC and chiral prep HPLC to give 4-[(6-chloropyridazin-3- yl)methoxy]-l – {6-[(tetrahydrofuran-3-ylamino)methyl]-3,4-dihydronaphthalen-2-yl}pyridin- 2(lH)-one hydrochloride as a yellow solid (peak 1 , 65 mg, 1 1.2percent yield): 1H NMR (400 MHz, CD3OD) delta ppm 8.05 (d, J = 7.2 Hz, 1H), 7.99 (d, J = 8.8 Hz, 1H), 7.93 (d, J = 8.8 Hz, 1H), 7.41-7.38 (m, 2H), 7.30-7.28 (m, 1H), 6.89-6.87 (m, 1H), 6.80 (s, 1H), 6.63 (d, J = 2.4 Hz, 1H), 5.64 (s, 2H), 4.23-4.21 (m, 2H), 4.06-3.95 (m, 3H), 3.86-3.82 (m, 1H), 3.75-3.72 (m, 1H), 3.1 1 -3.09 (m, 2H), 2.76-2.68 (m, 2H), 2.43-2.41 (m, 1H), 2.15-2.10 (m, 1H); ES- LCMS m/z 465 (M+H), and 4-[(6-chloropyridazin-3-yl)methoxy]-l – {6-[(tetrahydrofuran-3- ylamino)methyl]-3,4-dihydronaphthalen-2-yl}pyridin-2(lH)-one hydrochloride as a yellow solid (peak 2, 49.3 mg, 8.5percent yield): 1H NMR (400 MHz, CD3OD) delta ppm 7.98-7.93 (m, 3H), 7.41-7.38 (m, 2H), 7.30-7.28 (m, 1H), 6.85-6.79 (m, 2H), 6.61 -6.60 (m, 1H), 5.64 (s, 2H), 4.23-4.22 (m, 2H), 4.05-4.00 (m, 3H), 3.87-3.83 (m, 1H), 3.73-3.71 (m, 1H), 3.13-3.09 (m, 2H), 2.73-2.67 (m, 2H), 2.41-2.39 (m, 1H), 2.12-2.10 (m, 1H); ES-LCMS m/z 465 ( +H)+. Chiral HPLC method Instrument: Thar 80 Column: AS 250mm*20mm, 20um Mobile phase: A: Supercritical C02, B: MeOH, A: B =55:45 at 80mL/min Column Temp: 38¡ãC Nozzle Pressure: lOOBar Nozzle Temp: 60¡ãC Evaporator Temp: 20¡ãC Trimmer Temp: 25¡ãC Wavelength: 220nm

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

Reference£º
Patent; GLAXOSMITHKLINE LLC; QIN, Donghui; CHRISTENSEN, IV, Siegfried Benjamin; WU, Chengde; ZHANG, Zhiliu; YU, Haiyu; YUAN, Jiangxing; LIN, Xiaojuan; XU, Shanli; LV, Maoyun; YAO, Chen; LI, Lei; HUANG, Xing; GAO, Min; WO2013/166621; (2013); A1;,
Tetrahydrofuran – Wikipedia
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,453-20-3

To a suspension of sodium hydride (1.2 equiv, 60% by weight in mineral oil) in THF (0.3 M) under nitrogen atmosphere was added tetrahydrofuran-3-ol (1.5 equiv) in THF (0.6 M) at 0 C. The resulting reaction mixture was stirred at 0 C. for 20 min. A solution of 6-(2,4-dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole (1 equiv) in THF (0.6 M) was added and the resulting reaction mixture was stirred at room temperature for 3 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (0.6 M) and the organic solvents were removed under reduced pressure. The resulting residue was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated under reduced pressure and the crude product was purified by silica gel chromatography (15% ethyl acetate in petroleum ether) to afford the title compound (83% yield). MS (ESI) m/z 501.1 [M+H]+.

The synthetic route of 453-20-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Signal Pharmaceutical LLC; Calabrese, Andrew Antony; Jeffy, Brandon; Robinson, Dale; Zhu, Dan; Huang, Dehua; Elsner, Jan; Boylan, John; Tehrani, Lida; Nagy, Mark A.; Moghaddam, Mehran Fallah; Raheja, Raj Kumar; Erdman, Paul; Narla, Rama K.; Harris, Roy L.; Tran, Tam Minh; Riggs, Jennifer; Ning, Yuhong; US2014/200206; (2014); 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.184950-35-4,(Tetrahydrofuran-3-yl)methanamine hydrochloride,as a common compound, the synthetic route is as follows.

184950-35-4, 5- (2-phenoxyethyloxymethyl) isoxazole-3-carboxylic acid (1.40 g, 5.3 mmol), Tetrahydrofuran-3-ylmethylamine hydrochloride (0.88 g, 6.4 mmol), Triethylamine (0.65 g, 6.4 mmol) And 1-hydroxybenzotriazole (0.08 g, 0.64 mmol) were added to chloroform (amylene addition product) (20 mL). To the mixture, 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (1.23 g, 6.4 mmol) was added at room temperature, After stirring overnight, And concentrated under reduced pressure. Dilute hydrochloric acid was added to the concentrate, Extracted twice with ethyl acetate. The organic layer was washed with saturated brine, After drying with anhydrous sodium sulfate, And concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, Represented by the following equation N- (tetrahydrofuran-3-ylmethyl) -5- (2-phenoxyethyloxymethyl) isoxazole-3-carboxamide (Hereinafter referred to as present amide compound (149)) 1.60 g was obtained.

184950-35-4 (Tetrahydrofuran-3-yl)methanamine hydrochloride 17750392, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; SUMITA, YUSUKE; (264 pag.)JP2015/51963; (2015); 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.

(mixture of stereoisomers) (4-fluoro-2-hydroxyphenyl)-9-{[2-(trifluoromethoxy)phenyl]acetyl}-1,3,9-triazaspiro[5.5]- undecan-2-one (100 mg, 208 pmol, Intermediate 15), (3R)-oxolan-3-yl 4-methylbenzene-1 – sulfonate (75.5 mg, 312 pmol) and potassium carbonate (1 15 mg, 0.831 mmol) were mixed in dimethylformamide (1.2 ml_) and heated to 100 13 for 5 hours. The reaction was cooled down to room temperature, filtered and purified by preperative HPLC (Method 1 1) to give the title compound 65.0 mg (52 % yield). LC-MS (Method 4): Rt = 1.09 min; MS (ESIpos): m/z = 552 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) d [ppm]: 1.153 (0.98), 1.201 (1.22), 1.237 (2.54), 1.267 (2.20), 1.359 (2.88), 1.382 (2.54), 1.533 (1.66), 1.565 (1.46), 1.598 (1.56), 1.631 (1.32), 1.833 (0.83), 1.849 (1.12), 1.866 (1.37), 1.883 (1.17), 1.898 (1.07), 1.916 (1.12), 1.935 (1.37), 1.951 (1.71), 1.967 (1.80), 1.996 (0.88), 2.026 (0.78), 2.041 (0.73), 2.047 (1.32), 2.062 (1.71), 2.068 (0.73), 2.076 (0.59), 2.083 (1.46), 2.097 (0.98), 2.103 (0.59), 2.1 18 (0.54), 2.187 (1.41), 2.202 (2.00), 2.220 (2.29), 2.238 (1.90), 2.428 (16.00), 2.518 (11.56), 2.522 (7.02), 2.673 (2.05), 2.947 (1.22), 2.967 (1.17), 3.1 19 (0.88), 3.154 (1.61), 3.183 (2.29), 3.212 (1.27), 3.285 (3.37), 3.343 (7.22), 3.375 (4.00), 3.489 (0.68), 3.521 (1.71), 3.544 (3.41), 3.553 (4.15), 3.583 (4.10), 3.594 (3.85), 3.636 (2.88), 3.646 (7.37), 3.652 (10.29), 3.663 (5.66), 3.667 (3.46), 3.673 (5.02), 3.677 (3.27), 3.681 (4.10), 3.684 (4.73), 3.688 (4.10), 3.714 (3.80), 3.719 (4.24), 3.728 (3.32), 3.740 (4.59), 3.757 (8.05), 3.761 (6.34), 3.778 (8.00), 3.793 (6.98), 3.834 (3.46), 3.844 (3.76), 3.859 (1.85), 3.877 (2.34), 3.886 (2.29), 3.903 (1.90), 3.915 (1.66), 3.946 (1.71), 3.987 (2.05), 4.023 (0.88), 5.063 (2.39), 5.101 (2.29), 5.106 (2.15), 5.1 1 1 (2.29), 5.1 16 (2.15), 5.121 (1.41), 5.125 (1.12), 6.440 (6.15), 6.665 (5.66), 6.732 (1.46), 6.738 (1.80), 6.752 (3.85), 6.759 (3.66), 6.766 (2.93), 6.773 (3.80), 6.780 (2.20), 6.787 (1.61), 6.794 (1.51), 6.886 (3.12), 6.891 (3.17), 6.898 (2.88), 6.908 (2.63), 6.915 (3.22), 6.920 (3.22), 6.927 (2.63), 7.207 (6.10), 7.215 (12.34), 7.226 (9.85), 7.253 (10.68), 7.259 (8.68), 7.279 (3.66), 7.331 (2.00), 7.339 (4.00), 7.345 (4.00), 7.354 (3.56), 7.363 (3.95), 7.376 (1.76), 7.382 (1.22), 7.481 (3.61), 7.483 (4.20), 7.502 (4.68), 7.799 (5.95), 7.804 (1.80), 7.816 (1.76), 7.820 (5.32).

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

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; GRAHAM, Keith; AIGUABELLA FONT, Nuria; HEINRICH, Tobias; BRAeUER, Nico; LANGE, Martin; BADER, Benjamin; PRECHTL, Stefan; LIENAU, Philip; NOWAK-REPPEL, Katrin; POTZE, Lisette; STEUBER, Holger; NIU, Haitao; WANG, Qiuwen; (248 pag.)WO2020/48827; (2020); A1;,
Tetrahydrofuran – Wikipedia
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,88675-24-5

EXAMPLE 44: (2i?)-2-(6-fluoro-3-oxopyrrolo[4,3,2-Je][2,6]naphthyridin- 4(l/f,3/f,5H)-yl)-3-methyl-Lambda/-(tetrahydrofuran-3-yl)butanamide[0410] To an 8 mL scintillation vial equipped for stirring was added (i?)-2-(6-fluoro-3- oxopyrrolo[4,3,2-(ie][2,6]naphthyridin-4(lH,3H,5H)-yl)-3-methylbutanoic acid (15 mg, 0.051 mmol). DMF (0.5 mL), tetrahydrofuran-3 -amine (0.077, 6.7mg), HOBt (11.83 mg, 0.077 mmol), EDC (14.81 mg, 0.077 mmol) and N,N-dimethylpyridin-4-amine (9.44 mg, 0.077 mmol) were added and the solution was stirred at 25¡ãC for 4 h. The reaction mixture was purified via preparative mass trigger LC-MS (AcCN/H2O, 20-50percent). The fractions were collected and lyophilized to afford the title compound as a white solid (7.3mg, 39.3percent). 1H NMR (400 MHz, CD3OD) delta 0.93 (d, J=6.57 Hz, 3 H) 1.04 (dd, J=6.57, 2.78 Hz, 3 H) 1.74 -1.95 (m, 1 H) 2.21 (d, J=7.83 Hz, 1 H) 2.42 – 2.54 (m, 1 H) 3.50 – 3.67 (m, 1 H) 3.69 – 3.97 (m, 3 H) 4.37(td, J=3.85, 1.89 Hz, 1 H) 4.96 – 5.12 (m, 2 H) 5.36 – 5.52 (m, 1 H) 7.86 (s, 1 H) 8.17 (d, J=3.28 Hz, 1 H). [M+H] calc’d for Ci8H2IFN4O3, 361; found, 361.4.

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

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; DONG, Qing; LAWSON, John, David; WALLACE, Michael, B.; KANOUNI, Toufike; WO2010/144486; (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.

To a solution of toluene-4-sulfonic acid (R)-(tetrahydro-furan-3-yl) ester (1.5 g, 6.2 mmol) and Cs2C03 (1 .83 g, 5.6 mmol) in DMF (20 mL) was added 1 H-pyrazole-4-carboxylic acid ethyl ester (789 mg, 5.6 mol). The mixture was kept at 80C for 14 h. The volatiles were removed in vacuo and the residue was extracted with EtOAc (50 mL). The combined organic layers were washed with H20, dried over Na2S04 and evaporated to dryness. Flash chromatography (silica, petroleum ether: EtOAc 3:1 ) gave reagent 2 as a solid (1.07 g, 91 %). 1H NMR (CDCI3) delta 7.97 (s, 1 H), 7.90 (s, 1 H), 4.95-5.00 (m, 1 H), 4.27 (q, J = 6.4 Hz, 2 H), 4.01 -4.15 (m, 3 H), 3.90-3.96 (m, 1 H), 2.43-2.52 (m, 1 H), 2.27-2.34 (m, 1 H), 1.33 (t, J = 6.4 Hz, 3 H)., 219823-47-9

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

Reference£º
Patent; H. LUNDBECK A/S; ESKILDSEN, J¡ãrgen; WO2014/49133; (2014); 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

4-(3-(6-Hydroxypyridin-3-yl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile 10c (100 mg, 0.24 mmol) was placed in a reaction flask, followed by addition of (R)-tetrahydrofuran-3-yl-4-methylbenzenesulfonate 2a (116 mg, 0.48 mmol), cesium carbonate (235 mg, 0.72 mmol), and 3 mL of N,N-dimethylacetamide, successively. The reaction solution was warmed up to 60 C. and stirred for 2 hours. The reaction solution was cooled down to room temperature, mixed with 10 mL of saturated sodium chloride solution, and extracted with ethyl acetate (20 mL*3). The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by thin layer chromatography with elution system A to obtain the title compound (S)-4-(4,4-dimethyl-5-oxo-3-(6-((tetrahydrofuran-3-yl)oxy)pyridin-3-yl)-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile 24 (60 mg, yield 52.6%) as a white solid. MS m/z (ESI): 477.2 [M+1]; 1H NMR (400 MHz, CDCl3): delta 8.09-8.08 (m, 1H), 8.00-7.96 (m, 2H), 7.86-7.84 (m, 1H), 7.54-7.51 (m, 1H), 6.92-6.90 (m, 1H), 5.63-5.60 (m, 1H), 4.14-3.91 (m, 4H), 2.35-2.16 (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; US2015/225381; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

165253-29-2, 3-(Bromomethyl)tetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

165253-29-2, Example 106 Preparation of 3-(3-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-7-(3,5-dimethyl-l- ((tetrahydrofuran-3-yl)methyl)-lH-pyrazol-4-yl)-2-methyl-lH-indol-l-yl)propanoic acid Title compound was prepared (5.0 mg, 0.008 mmol) according to procedures described in Example 105 by using 3-(3-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-7-(3,5-dimethyl-lH- pyrazol-4-yl)-2-methyl-lH-indol-l-yl)propanoic acid (25 mg, 0.05 mmol), cesium carbonate (82.4 mg, 0.25 mmol) and 3-(bromomethyl)tetrahydrofuran (16 mu,, 0.15 mmol). MS (ES) 578.2 (M+H), tR: 1.480 min.

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

Reference£º
Patent; VANDERBILT UNIVERSITY; LEE, Taekyu; KIM, Kwangho; CHRISTOV, Plamen P.; BELMAR, Johannes; BURKE, Jason P.; OLEJNICZAK, Edward T.; FESIK, Stephen W.; WO2015/31608; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

3123-97-5, 5,5-Dimethyldihydrofuran-2(3H)-one is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of the Compound 1 (5.13 g) and the Compound 2 (1.3 mE) in methanol (45 mE) was added dropwise concentrated sulfuric acid (350 pL), and the resulting mixture was stirred at 50¡ã C. for 2 hours. To the reaction mixture was added a saturated aqueous solution of sodium hydrogen carbonate at room temperature to alkali1,? the mixture, and chloroform was added thereto, and the resulting mixture was stirred. The resulting organic layers were separated, then washed with saturated brine, dried, andconcentrated under reduced pressure. The resulting residues were purified by silica gel column chromatography (hexane:ethyl acetate=97:3 to 85:15) to give the Compound 3 (6.2 g) as a pale yellow liquid. 1H-NMR (CDC13) oe 1.15 (s, 6H), 1.80-1.84 (m, 2H), 2.34-2.38 (m, 2H), 3.17 (s, 3H), 3.67 (s, 3H)

3123-97-5, 3123-97-5 5,5-Dimethyldihydrofuran-2(3H)-one 18398, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; MITSUBISHI TANABE PHARMA CORPORATION; SATO, Atsushi; IMASHIRO, Ritsuo; TSUJISHIMA, Hidekazu; TANIMOTO, Kouichi; YAMAMOTO, Yasuo; NAKANE, Tetsu; TOSHIKAWA, Chihiro; (118 pag.)US2018/258076; (2018); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem