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.

1-chloro-4-(beta-D-glucopyranos-1-yl)-2-[4-((S)-tetrahydrofuran-3-yloxy)-benzyl]-benzene 0.19 g (R)-3-(4-methylphenylsulfonyloxy)-tetrahydrofuran are added to a mixture of 0.20 g 1-chloro-4-(beta-D-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene and 0.29 g cesium carbonate in 2.5 ml dimethylformamide. The mixture is stirred at 75 C. for 4 h, before another 0.29 g caesium carbonate and 0.19 g (R)-3-(4-methylphenyl-sulfonyloxy)-tetrahydrofuran are added. After an additional 14 h stirring at 75 C. the mixture is cooled to ambient temperature and brine is added. The resulting mixture is extracted with ethyl acetate, the combined organic extracts are dried over sodium sulfate, and the solvent is removed. The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0?5:1). Yield: 0.12 g (49% of theory) Mass spectrum (ESI+): m/z=451/453 (Cl) [M+H]+, 219823-47-9

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

Reference£º
Patent; Boehringer Ingelheim International GmbH; US2007/249544; (2007); A1;,
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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, To a stirred solution of intermediate 1 (0.21 g, 0.9 mmol) and TEA (0.37 mL, 2.7 mmol) in dry DCM (5 mL) at 0 ¡ãC, triphosgene (0.268 g, 0.90 mmol) was added and stirred for 2 h at RT. Completion of the reaction was monitored by TLC. The reaction mixture was then poured into water (10 mL) and stirred for 10 min. The organic layer was washed with brine (10 mL), dried over anhydrous Na2S04 and evaporated under vacuum. The resulting crude mixture was dissolved in dry DCM (10 mL), then TEA (0.37 mL, 2.7 mmol) followed by tetrahydrofuran-3- amine (0.12 g, 1.35 mmol) were added at 0 ¡ãC under nitrogen atm and stirred for 4 h at RT. Completion of the reaction was moitored by TLC. The mixture was poured into sat. NaHCO3 (10 mL) and the resulting mixture was stirred for 10 min. The organic layer was washed with brine (10 mL), dried over anhydrous Na2S04 and concentrated under vacuum. The resulting crude material was purified by flash chromatography (Biotage Isolera, gradient: 7percent methanol in DCM) to afford the title compound. Yield: 10percent (31.34 mg, white solid). 1H NMR (400 MHz, DMSO-ak) : delta 7.13 (d, J = 7.6 Hz, 1 H), 6.72 (d, J = 7.2 Hz, 1 H), 6.68 (s, 1 H), 6.38 (d, J = 5.6 Hz, 1 H), 4.49 (t, J = 8.4 Hz, 2H), 4.12-4.05 (m, 1 H), 3.79-3.70 (m, 2H), 3.63-3.57 (m, 1 H), 3.40-3.30 (m, 1 H), 3.27-3.20 (m, 4H), 3.12 (t, J = 8.4 Hz, 2H), 2.33-2.25 (m, 3H), 2.21-2.17 (m, 2H), 2.05-1.95 (m, 1 H), 1.79-1.68 (m, 1 H), 1.2 (d, J = 6.4 Hz, 3H). LCMS: (Method A) 346.3 (M+H), Rt. 2.0 min, 96.3percent (Max). HPLC: (Method A) Rt. 2.1 min, 96.3percent (Max).

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

Reference£º
Patent; ASCENEURON S.A.; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; (134 pag.)WO2019/37860; (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.184950-35-4,(Tetrahydrofuran-3-yl)methanamine hydrochloride,as a common compound, the synthetic route is as follows.

Tetrahydrofuran-3-ylmethylamine hydrochloride (0.07 g, 0.49 mmol) And triethylamine (0.05 g, 0.49 mmol) Was added to chloroform (amylene addition product) (3 mL). To the mixture, At room temperature 5- (1,4-benzodioxan-2-ylmethyl) oxymethyl isoxazole-3-carboxylic acid (0.12 g, 0.41 mmol) 1-Hydroxybenzotriazole (0.01 g, 0.04 mmol) And 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.10 g, 0.49 mmol) were added, After stirring at room temperature for 6 hours, Dilute hydrochloric acid was added, It was extracted twice with chloroform. The organic layer was washed with saturated sodium bicarbonate water, After drying with anhydrous sodium sulfate, It was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, Represented by the following equation N- (tetrahydrofuran-3-ylmethyl) -5- (1,4-benzodioxan-2-ylmethyl) oxymethyl isoxazole-3-carboxamide (Hereinafter referred to as the present amide compound (120)) 0.08 g was obtained.

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;,
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105-21-5, Gamma-heptalactone is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a dry round bottom flask under argon atmosphere 5 g (27.9 mmol) of (3- aminopropyl)trimethoxysilane (AMMO) was stirred at 50 C. 0.28 ml of 1 M triethylaluminium solution in hexane was slowly added (0.279 mmol, 1 mol%). Afterwards 27.9 mmol of the mono-substituted lactone listed in Table 1 was added and vigorously stirred for 3 hours. (0070) A yellowish and viscous following product from Comparative Example 1 was obtained. (0071) (0072) 1H NMR (400 MHz, Chloroform-c/) d 6.55 (s, OH), 3.51 (s, 5H), 3.19 – 3.12 (m, 1 H), 2.32 – 2.26 (m, 1 H), 1.84 – 1.71 (m, 1 H), 1.65 – 1.49 (m, 2H), 1.37 (m, 2H), 0.86 (t, J = 7.0 Hz, 1 H), 0.63 – 0.55 (m, 1 H); 13C NMR (101 MHz, CDCIs) d = 173.95, 70.74, 50.46, 41.92, 39.78, 33.10, 32.81 , 22.62, 18.86, 14.03, 6.45; 29Si NMR (79 MHz, CDCIs) d = -42.22.

105-21-5, As the paragraph descriping shows that 105-21-5 is playing an increasingly important role.

Reference£º
Patent; HENKEL AG & CO. KGAA; DAMKE, Jan-Erik; KLEIN, Johann; BRISAR, Rok; MEJIA, Esteban; (16 pag.)WO2019/115321; (2019); A1;,
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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, Step A. (+/-)-N-(2-Nitrophenyl)tetrahvdrofuran-3 -amineA solution of N, jV-diisopropylethylamine (3.20 mL, 18.4mmol), l-fluoro-2- nitrobenzene (0.484 mL, 4.59 mmol), and (+/-)-tetrahydrofuran-3 -amine (400 mg, 4.59 mmol) in rc-butanol (10 mL) was heated to 180 0C in a microwave reactor. After 20 min, the reaction was allowed to cool to ambient temperature and concentrated. Purification by silica gel chromatography, eluting with a gradient of hexane: EtOAc – 100:0 to 0:100, gave the title compound. MS: mlz = 209 (M + 1).

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

Reference£º
Patent; MERCK & CO., INC.; WO2008/130512; (2008); 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- (3-chloro-4-fluorobenzyloxymethyl) isoxazole-3-carboxylic acid (2.55 g, 8.9 mmol), Tetrahydrofuran-3-ylmethylamine hydrochloride (1.84 g, 13.4 mmol), Triethylamine (1.87 mL, 13.4 mmol) And 1-hydroxybenzotriazole (0.12 g, 0.9 mmol) Was added to chloroform (amylene added product) (20 mL). To the mixture, 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (2.05 g, 10.7 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- (3-chloro-4-fluorobenzyloxymethyl) isoxazole-3-carboxamide (Hereinafter referred to as the present amide compound (261)) 0.29 g was obtained., 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

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

To a solution of (S)-3-(1,4-dimethyl-1H-benzo[d][1,2,3]triazol-5-yl)-3-(3-(((R)-2-ethyl-2,3- dihydropyrido[3,4-f][1,4]oxazepin-4(5H)-yl)methyl)-4-methylphenyl)-2,2-dimethylpropanoic acid (100 mg, 0.190 mmol) and tetrahydrofuran-3-amine (19.81 mg, 0.227 mmol) in N,N- dimethylformamide (DMF) (1 mL) was added DIEA (0.099 mL, 0.569 mmol) and HATU (72.1 mg, 0.190 mmol). The mixture was allowed to stir at 25 C for 20 hrs. The reaction was then diluted with water and extracted with ethyl acetate (3×30 mL). The combined organic layer was dried over magnesium sulfate, filtered, and concentrated to dryness. The residue was dissolved in 3 mL of DMSO, filtered, and purified by reverse phase preparative HPLC under neutral conditions to obtain the title compound (42.9 mg, 0.072 mmol, 37.9 % yield) as a colorless solid. LC-MS m/z 598.5 (M+H)+, 0.88 min (ret. time).1H NMR (400 MHz, METHANOL-d4) deltappm 0.82 – 1.00 (m, 3 H) 1.30 – 1.39 (m, 7 H) 1.39 – 1.68 (m, 3 H) 1.89 – 2.04 (m, 1 H) 2.26 (s, 3 H) 2.68 – 2.90 (m, 5 H) 3.17 – 3.29 (m, 1 H) 3.55 – 3.78 (m, 6 H) 3.81 – 3.99 (m, 2 H) 4.15 – 4.33 (m, 4 H) 4.89 (d, J=7.53 Hz, 1 H) 6.98 (d, J=5.52 Hz, 1 H) 7.04 – 7.19 (m, 3 H) 7.48 (d, J=8.78 Hz, 1 H) 7.69 – 7.80 (m, 1 H) 8.09 (s, 1 H) 8.30 (d, J=5.27 Hz, 1 H)

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

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CALLAHAN, James Francis; COLANDREA, Vincent J.; COOPER, Anthony William James; GOODWIN, Nicole Cathleen; HUFF, Chelsea Ariane; KARPIAK, Joel; KERNS, Jeffrey K.; NIE, Hong; (404 pag.)WO2018/109647; (2018); A1;,
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97-99-4, (Tetrahydrofuran-2-yl)methanol is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of (R)-(tetrahydrofuran-2-yl)methanol (1.0 g, 9.8 mmol) in CH2Cl2 (3 mL) and pyridine (3 mL) at ambient temperature was added 4-methylbenzene-1-sulfonyl chloride (2.0 g, 10.3 mmol) portionwise over 5 min. The mixture was stirred for 16 hours at ambient temperature then quenched by the addition of 5% aqueous HCl (10 mL). The layers were separated and the aqueous phase was extracted with CH2Cl2 (3¡Á5 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purifined by column chromatography (SiO2, 75% hexanes in EtOAc) to afford the title compound (1.7 g, 6.8 mmol, 69% yield). MS (DCI/NH3) m/z 257 (M+H)+ and 274 (M+NH4)+, 97-99-4

97-99-4 (Tetrahydrofuran-2-yl)methanol 7360, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; ABBOTT LABORATORIES; US2010/69348; (2010); A1;,
Tetrahydrofuran – Wikipedia
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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

Compound 102 A mixture of (5)-tetrahydrofuran-3-amine hydrochloride (11.2 g, 90.7 mmol) and NEt3 (50.5 mL, 362.6 mmol) in dry CH2CI2 (400 mL) was stirred for 5 minutes at 20 C. 3-(chlorosulfonyl)benzoic acid (20 g, 90.7 mmol) was added and the mixture was stirred overnight at 20C. The reaction mixture was washed with IN HCl (100 mL), the aqueous layer was extracted with dichloromethane (2 x 200 mL). The combined organic layers were dried over Na2S04 and the solvent was removed in vacuo, resulting in 3-[[(35)-tetrahydrofuran-3-yl]sulfamoyl]benzoic acid (16.3 g). 3-[[(35)-tetrahydro- furan-3-yl]sulfamoyl]benzoic acid (3 g, 11.058 mmol), 3-(difluoromethyl)-4-fluoro- aniline (2.1 g, 13.3 mmol) and triethylamine (3.3 g, 33 mmol) were dissolved in DMF (400 mL). PyBrOP (132705-51-2, 6.2 g , 13.3 mmol) was added at 0C. The mixture was stirred at 50C for 12 hours. The solvent was removed in vacuo and the obtained residue was purified by reversed phase high performance liquid chromatography (mobile phase: CH3CN in water (0.1% TFA) from 30% to 60%). The pure fractions were collected and neutralized with solid NaHC03. The organic solvent was removed in vacuo and the formed precipitate was filtered, washed with H20 (5 mL) and dried under high vacuum. The obtained residue was suspended in water (5 mL) and lyophilized to dryness resulting in compound 102 (2.3 g). Method A; Rt: 5.32 min. m/z : 415.2 (M+H)+ Exact mass: 414.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.53 – 1.68 (m, 1 H) 1.82 – 1.99 (m, 1 H) 3.27 – 3.42 (m, 1 H) 3.51 – 3.90 (m, 4 H) 7.26 (t, J=55 Hz, 1 H) 7.36 – 7.51 (m, 1 H) 7.80 (t, J=7.8 Hz, 1 H) 7.92 – 8.00 (m, 1 H) 8.01 – 8.08 (m, 1 H) 8.08 – 8.15 (m, 2 H) 8.25 (d, J=7.8 Hz, 1 H) 8.40 (s, 1 H) 10.75 (s, 1 H).

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; WO2014/33170; (2014); A1;,
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97-99-4, (Tetrahydrofuran-2-yl)methanol is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

97-99-4, General procedure: To a solution of optically pure tetrahydrofurfuryl alcohol (6 or 16) in pyridine was added 1 eq of p-toluenesulfonyl chloride portionwise at 0 , then the reaction mixture was stirred for 3 h. The mixture was poured into a large amount of ice water with violent agitation, and the solid phase was filtered and recrystallized with methanol to give tosylate 7 or 17 as white solids. For 7: 92% yield, deltaH (500 MHz; CDCl3; Me4Si) 1.67-1.69 (m, 1 H), 1.85-1.87 (m, 2 H), 1.94-1.99 (m, 1 H), 2.44 (s, 3 H), 3.70-3.80 (m, 2 H), 3.97-4.10 (m, 3 H), 7.33 and 7.79 (d, J = 8.2 Hz, each 2 H); ESI-MS m/z: 279.1 [M+Na]+; For 17: 96% yield, deltaH (500 MHz; CDCl3; Me4Si) 1.60-1.70 (m, 1 H), 1.83-1.90 (m, 2 H), 1.94-2.01 (m, 1 H), 2.44 (s, 3 H), 3.70-3.81 (m, 2 H), 3.97-4.03 (m, 2 H), 4.06-4.10 (m, 1 H), 7.33 and 7.79 (d, J = 8.2 Hz, each 2 H); ESI-MS m/z: 267.1 [M+Na]+.

97-99-4 (Tetrahydrofuran-2-yl)methanol 7360, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Article; Hao, Jia; Chen, Bo; Yao, Yiwu; Hossain, Murad; Nagatomo, Takafumi; Yao, Hequan; Kong, Lingyi; Sun, Hongbin; Bioorganic and Medicinal Chemistry Letters; vol. 22; 10; (2012); p. 3441 – 3444;,
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