Heterocyclic Building Blocks-Tetrahydrofuran

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 solution of 2-fluoro-4-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indazol-1-yl)-benzonitrile (491 mg, 1.65 mmol) in DMSO (0.7 mL), (S)-3-aminotetrahydrofuran hydrochloride (247 mg, 1.98 mmol) and DIEA (0.86 mL, 4.95 mmol) are added, and the reaction is stirred at 90 C. for 13 hours. The reaction mixture is then diluted with EtOAc (50 mL), washed with H2O (2¡Á50 mL) and brine (50 mL), and the organic layers are dried over Na2SO4 and concentrated. Purification of the residue using a Biotage column (elution with 0-100% EtOAc in hexanes) yields (S)-2-(tetrahydrofuran-3-ylamino)-4-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indazol-1-yl)benzonitrile (197 mg, 33% yield) as a light yellow solid. LCMS: m/z=365 [M+H]+., 204512-95-8

As the paragraph descriping shows that 204512-95-8 is playing an increasingly important role.

Reference£º
Patent; Huang, Kenneth He; Ommen, Andy J.; Barta, Thomas E.; Hughes, Philip F.; Veal, James; Ma, Wei; Smith, Emilie D.; Woodward, Angela R.; McCall, W. Stephen; US2008/269193; (2008); 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.

Compound 101 (S)-tetrahydrofuran-3 -amine hydrochloride (5.17 g, 42 mmol) and NaOH (5 g, 126 mmol) were dissolved in THF (50 mL) and H20 (50 mL). 5-(chlorosulfonyl)-2- fluorobenzoic acid (10 g, 42 mmol) was added at 0C. The mixture was stirred at 20C for 4 hours. The mixture was washed with ethyl acetate (3 x 20 mL). The aqueous layer was separated and adjusted to pH=3 with IN HC1. The aqueous layer was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine and dried over Na2S04. The solvent was removed in vacuo resulting in (S)-2-fluoro-5- (N-(tetrahydrofuran-3-yl)sulfamoyl)benzoic acid (2.1 g) . (S)-2-fluoro-5-(N-(tetra- hydrofuran-3-yl)sulfamoyl)benzoic acid (1 g, 3.457 mmol), 3,4-difluoroaniline (0.53 g, 4.15 mmol) and triethylamine (0.7 g, 6.9 mmol) were dissolved in DMF (400 mL) and HATU (1.57 g , 4.15 mmol) was added at 0C. The mixture was next stirred at 20C for 6 hours. The solvent was removed in vacuo and the obtained residue was purified by silica gel chromatography (eluent: petroleum ether: ethyl acetate=5 : l) resulting in compound 101 (0.8 g). Method B; Rt: 4.15 min. m/z : 401.3 (M+H)+ Exact mass: 400.1

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

Reference£º
Patent; JANSSEN R&D IRELAND; LAST, Stefaan, Julien; RABOISSON, Pierre, Jean-Marie, Bernard; ROMBOUTS, Geert; VANDYCK, Koen; VERSCHUEREN, Wim, Gaston; WO2014/33176; (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.

5- (1,1-difluoro-1-phenylmethyl) isoxazole-3-carboxylic acid chloride ( Was added tetrahydrofuran-3-ylmethylamine hydrochloride (200 mg, 1.45 mmol) in toluene solution (10 mL) And 1 mol / L sodium hydroxide aqueous solution (10 mL) were simultaneously added under cooling with ice water. After vigorously stirring for 1 hour under cooling with ice water, The reaction mixture was 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- (1,1-difluoro-1-phenylmethyl) isoxazole-3-carboxamide (Hereinafter referred to as the present amide compound (155)) 190 mg., 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;,
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.17347-61-4,2,2-Dimethylsuccinicanhydride,as a common compound, the synthetic route is as follows.

Step F: Compound 19-1 To a solution of the intermediate 18-1 (70 mg, 0.13 mmol) in pyridine (3 mL) were added 3,3-dimethyldihydro-2, 5-furandione (159 mg, 1.302 mmol) and DMAP (334 mg, 2.6 mmol). After it was heated at 90 ¡ãC overnight, the reaction mixture was extracted with DCM. The organic phase was washed with HC1 (2 N, 25 mL), water (50 mL x 2), dried over sodium sulfate, and evaporated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (PE:EtOAc = 3: 1 to 2: 1) to give the compound 19-1 (30 mg, 34.6 percent) as a white solid product. 1H NMR (400 MHz, CDC13) delta ppm 4.54-4.42 (2H, m), 4.28-4.35 (1H, m), 4.05-4.15 (2H, m), 3.17-3.25 (1H, m), 2.75- 2.62 (4H, m), 2.60-2.52 (2H, m), 2.35(1H, quint, J= 8.0 Hz), 2.17 (1H, d, J= 19.2 Hz), 2.10-2.00 (1H, m), 1.96-1.82 (1H, m), 1.78-0.78 (42H, m). LC/MS: m/z calculated 665.9, found 664.4 (M – 1)-., 17347-61-4

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

Reference£º
Patent; GLAXOSMITHKLINE LLC; GAO, Daxin; HAN, Nianhe; JIN, Zhimin; NING, Fangxian; TANG, Jun; WU, Yongyong; YANG, Heping; WO2011/100308; (2011); 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.124391-75-9,(S)-(Tetrahydrofuran-3-yl)methanol,as a common compound, the synthetic route is as follows.

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;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

19311-37-6, 3-Bromotetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Cesium carbonate (0.9 g, 2.8 mmol) was added to a solution of N-(4-((7-hydroxy-6-methoxyquinazolin-4-yl)oxy)phenyl)-2-( 4-isopropyl-1H-1 ,2,3-triazol-1-yl)acetamide (0.4 g,0.9 mmol) and 3-bromotetrahydrofuran (0.7 g, 4.6 mmol) in DMF (3 mL) under nitrogen. The5 resulting mixture was stirred at 100C for 3 hours. The crude product was purified bypreparative HPLC. Fractions containing the desired product were combined and concentratedunder vacuum to afford racemic title compound as a white solid (180 mg, 39%). This waspurified by preparative SFC-HPLC. The first eluting fractions containing the desiredcompound were evaporated to dryness to afford one enantiomer of 2-(4-isopropyl-1H-1,2,3-10 triazol-1-yl)-N-( 4-( (6-methoxy-7 -((tetrahydrofuran-3-yl)oxy)quinazolin-4-yl)oxy)phenyl)acetamide as a white solid (69 mg, 38%, 100% e.e.). 1H NMR (400 MHz,DMSO-d6) 8 1.26 (6H, d), 2.06-2.08 (lH, m), 2.38-2.40 (lH, m), 3.01-3.03 (lH, m), 3.74-4.03 (7H, m), 5.31 (3H, d), 7.26-7.34 (2H, m), 7.37 (lH, s), 7.58 (lH, s), 7.64-7.76 (2H, m),7.90 (lH, d), 8.55 (lH, s), 10.60 (lH, s); m/z: ES+ [M+H]+ 505. This was followed by the15 other enantiomer of 2-( 4-isopropyl-1H-1 ,2,3-triazol-1-yl)-N-( 4-(( 6-methoxy-7-((tetrahydrofuran-3-yl)oxy)quinazolin-4-yl)oxy)phenyl)acetamide (67 mg, 37%, 100% e.e.) asa white solid. 1H NMR (400 MHz, DMSO-d6) 8 1.26 (6H, d), 2.06-2.08 (lH, m), 2.38-2.40(lH, m), 3.01-3.03 (lH, m), 3.74-4.03 (7H, m), 5.28- 5.36 (3H, m), 7.25-7.34 (2H, m), 7.37(lH, s), 7.57 (lH, s), 7.64 – 7.73 (2H, m), 7.90 (lH, d), 8.55 (lH, s), 10.57 – 10.63 (lH, m);20 m/z: ES+ [M+H]+ 505., 19311-37-6

The synthetic route of 19311-37-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; GRECU, Tudor; KETTLE, Jason, Grant; PACKER, Martin, John; PEARSON, Stuart, Eric; SMITH, James, Michael; (58 pag.)WO2018/197643; (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.111769-27-8,(R)-Tetrahydrofuran-3-amine 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

To a mixture of l-(5,6-dichloro-l-(8-chloroquinolin-2-yl)-lH-benzo[111769-27-8, As the paragraph descriping shows that 111769-27-8 is playing an increasingly important role.

Reference£º
Patent; NOVASAID AB; WANNBERG, Johan; ALTERMAN, Mathias; MALM, Johan; WO2012/117062; (2012); 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

10492] To a solution of 235-1 ( 1.82 g, 10.0 mmol), tetrahydrofuran-3-ol (880 mg, 10.0 mmol) and PPh3 (2.62 g, 10.0 mmol) in THF (30 mL) at 0 C was added DIAD (2.02 g, 10.0 mmol) dropwise. The mixture was stirred at 0 C for 2 h, and the reaction was then quenched with sat. NaHC03 solution. The aqueous layer was extracted by DCM (3x). The combined organic layers were dried over MgSC>4, filtered and concentrated at low pressure. The residue was purified by flash column chromatography on silica gel to give 235-2 (2.4 g, 89.6%)., 453-20-3

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

Reference£º
Patent; ALIOS BIOPHARMA, INC.; WANG, Guangyi; BEIGELMAN, Leonid; TRUONG, Anh; NAPOLITANO, Carmela; ANDREOTTI, Daniele; HE, Haiying; STEIN, Karin, Ann; WO2015/26792; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

4100-80-5, 3-Methyldihydrofuran-2,5-dione is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE 13 Preparation of 6-(p-chlorophenyl)-8-methyl-1,2,4-triazolo[4,3-b]pyridazine To a solution of 114 g. of methylsuccinic anhydride in 400 ml. of chlorobenzene is added carefully 270 g. of aluminum chloride. The mixture is heated to 65¡ã C. for 11/2 hours, is cooled, quenched with ice and concentrated hydrochloric acid and extracted with benzene. The benzene layer is extracted with aqueous sodium bicarbonate. After adjusting the pH of the bicarbonate solution to 6.3, concentrated hydrochloric acid is added slowly over a period of several hours with stirring. At pH 5.7, 78 g. of white crystals are filtered off. Recrystallization of this material from ethanol-water affords 3-(p-chlorobenzoyl)-2-methylpropionic acid as white crystals.

4100-80-5, The synthetic route of 4100-80-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; American Cyanamid Company; US4117130; (1978); 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.

Step 2: Synthesis of 4-Bromo-1 -[(3S)-tetrahydrofuran-3-yl]pyrazole 3.6A mixture of 650 mg [(3R)-tetrahydrofuran-3-yl] 4-methylbenzenesulfonate, 400 mg 4-bromo- 1 H-pyrazole and 1 .40 g cesium carbonate in 10 mL Nu,Nu-dimethylformamide (DMF) was stirred at 65 C for 6 h. Additional 20 mg 4-bromo-1 H-pyrazole were added and the reaction mixture was stirred at 65 C overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (cyclohexane/ethyl acetate 9:1 ->1 :1 ) to yield 476 mg of 4-bromo-1 -[(3S)-tetrahydrofuran-3- yl]pyrazole 3J3 as solid.Analysis: MS: M+H = 217 / 219

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

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; DAHMANN, Georg; HOFFMANN, Matthias; KLICIC, Jasna; LAMB, David James; MCCARTHY, Clive; NAPIER, Spencer; PARRISH, Karen; SCOTT, John; SWANTEK FITZGERALD, Jennifer L.; WALKER, Edward; WO2015/140054; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem