Heterocyclic Building Blocks-Tetrahydrofuran

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

Step 2: Preparation of (S)-4,4,5,5-tetramethyl-2-(4-(tetrahydrofuran-3-yloxy)phenyl)-1,3,2-dioxaborolane A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (5 g, 22.8 mmole), (R)-tetrahydrofuran-3-yl 4-methylbenzenesulfonate (6.6 g, 22.8 mmol) and K2CO3 (8.0 g, 58 mmole) in DMF (25 mL) was heated at 85 C. for 15 h. The reaction mixture was diluted with ethyl acetate, washed with water, dried over MgSO4, filtered, and concentrated under vacuum The residue was purified by flash chromatography (silica gel, elute: 5% ethyl acetate in hexane) to give the title compound (2.4 g, 30% yield). MS (ESI) m/z: Calc. 290.2 (M+). Found: 291.1 (M+1)., 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; Cystic Fibrosis Foundation Therapeutics, Inc.; US8334292; (2012); B1;,
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

Production Example 22 (0333) 5-(3-Phenylpropyl)isoxazole-3-carboxylic acid (0.46 g, 2.0 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (0.33 g, 2.4 mmol), triethylamine (0.24 g, 2.4 mmol) and 1-hydroxybenzotriazole (0.04 g, 0.24 mmol) were added to chloroform (amylene addition product) (5 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.46 g, 2.4 mmol) was added to the mixture at room temperature, and the mixture was stirred overnight and then concentrated under reduced pressure. Dilute hydrochloric acid was added to the concentrate, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 0.49 g of N-(tetrahydrofuran-3-ylmethyl)-5-(3-phenylpropyl)isoxazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (22)) represented by the following formula. 1H-NMR (CDCl3, TMS, delta(ppm) :1.62-1.72 (1H, m), 2.02-2.13(3H, m), 2.52-2.62(1H, m), 2.69(2H, t), 2.80(2H, t), 3.44-3.47 (2H, m), 3.57-3.60(1H, m), 3.75-3.78(1H, m), 3.84-3.94(2H, m), 6.46(1H, s), 6.93(1H, br s), 7.18-7.22(3H, m), 7.29-7.32(2H, m)

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; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (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.97-99-4,(Tetrahydrofuran-2-yl)methanol,as a common compound, the synthetic route is as follows.

Example 193 : (R)-N-( 1 -Methyl- 1 H-pyrazo 1-4-yl)- 1 -((6-((tetrahydrofuran-2- yl)methoxy)pyridin-2-yl)methyl)- 1 H-pyrazo lo [3 ,4-d]pyrimidin-6-amine(R)-(Tetrahydrofuran-2-yl)methanol (22mg, 0.214mmol) was added to a solution of NaH (lOmg, 0.246mmol) in dry DMF (ImL) in a 2-necked flask under Nitrogen. Another portion of NaH (lOmg, 0.246mmol) was added to a stirring solution of l-((6-fluoropyridin-2- yl)methyl)-N-( 1 -methyl- 1 H-pyrazo 1-4-yl)- 1 H-pyrazolo [3 ,4-d]pyrimidin-6-amine (Example 170) (50mg, 0.154mmol) in DMF (1ml). This solution was added to the 2-necked flask and stirred for 16h at rt. The reaction was quenched with NH4C1 (sat. solution, ImL) and diluted with Ethyl Acetate (20mL). The organics were separated and washed with NaHC03 (sat. solution, 20mL). The aqueous phase was re-extracted with Ethyl Acetate (2 x lOmL). The combined organics were dried over Na2S04, filtered and the solvent evaporated to give a crude product that was purified by prep HPLC. (R)-N-( 1 -methyl- 1 H-pyrazo 1-4-yl)- 1 -((6- ((tetrahydrofuran-2-yl)methoxy)pyridin-2-yl)methyl)- 1 H-pyrazo lo [3 ,4-d]pyrimidin-6-amine was obtained as a white solid (24mg, 38% yield). 1H NMR (d6-Acetone) delta 8.87 (s, 1H), 8.04 (s, 1H), 7.99 (s, 1H), 7.61 (s and t, 2H), 6.70 (d, 1H), 6.64 (d, 1H), 5.54 (s, 2H), 4.07 (m, 3H), 3.82 (s, 3H), 3.75 (m, 1H), 3.61 (m, 1H), 1.84 (m, 3H), 1.54 (m, 1H); LC-MS method B, (ES+) 407.1, RT = 7.65min., 97-99-4

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

Reference£º
Patent; CELLZOME LIMITED; RAMSDEN, Nigel; HARRISON, Richard John; OXENFORD, Sally; BELL, Kathryn; PITON, Nelly; DAGOSTIN, Claudio; BOUSSARD, Cyrille; RATCLIFFE, Andrew; WO2011/48082; (2011); A1;,
Tetrahydrofuran – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.86087-24-3,(R)-Tetrahydrofuran-3-ol,as a common compound, the synthetic route is as follows.,86087-24-3

In an ice bath, 1,4-diazabicyclo[2.2.2]octane (2.52 g, 22.47 mmol) and p-toluenesulfonyl chloride (4.28 g, 22.45 mmol) were added to a solution of (R)-tetrahydrofuran-3-methanol (0.9 mL, 11.24 mmol) in dichloromethane (10 mL) respectively. After the addition, the reaction solution was warmed to room temperature and stirred for 1 hour. The reaction solution was diluted with dichloromethane (30 mL) and washed with water (30 mL). The organic phase was dried over anhydrous sodium sulfate and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate=30:1) to give 15-c (2.17 g, yield 80%).

The synthetic route of 86087-24-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GUANGZHOU MAXINOVEL PHARMACEUTICALS CO., LTD.; XU, Zusheng; ZHANG, Nong; WANG, Tinghan; SUN, Qingrui; WANG, Yuguang; (90 pag.)US2018/208604; (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.124391-75-9,(S)-(Tetrahydrofuran-3-yl)methanol,as a common compound, the synthetic route is as follows.

Example 1; Preparation of 1-{(tetrahydro-3-furanyl)methyl}-2-nitro-3-methylguanidine(dinotefuran);A mixture comprising 10.0 g of (tetrahydro-3-furanyl)methanol, 29.5 g of trifluoromethanesulfonic anhydride, 10.0 g of pyridine and 200 ml of dichloromethane was stirred for an hour at room temperature. Water was poured into the reaction solution to separate the organic layer, which was washed with 1 N hydrochloric acid, water and a saturated saline solution, dried, and concentrated to obtain 20 g of 3-tetrahydro-furanylmethyl triflate. 3.25 g of 60percent sodium hydride were added to 12.5 g of 1,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine and 60 ml of DMF at room temperature, followed by stirring for an hour. 20.0 g of the 3-tetrahydrofuranylmethyl triflate were added thereto, and the mixture was stirred at 50¡ã C. for 2 hours. After cooling the mixture to room temperature, 50 ml of 2N hydrochloric acid were added thereto, followed by stirring at 50¡ã C. for 2 hours. The resultant mixture was neutralized with sodium bicarbonate and extracted with dichloromethane, and the extract was dried and concentrated. The residue thus obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/1) to obtain 7.8 g of 1-{(tetrahydro-3-furanyl)methyl}-2-nitro-3-methylguanidine (dinotefuran)., 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; Cottrell, Ian W.; Ahn, Albert; Dorneval, Linda; US2007/254927; (2007); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

104227-71-6, (S)-tert-Butyl (5-oxotetrahydrofuran-3-yl)carbamate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: At -10 C,Diisopropylamine (436 mg, 4.3 mmol) and n-butyllithium (2.5 M, 1.7 mL,A solution of 4.3 mmol) in tetrahydrofuran (1 mL) was stirred for 10 minutes and then the reaction was cooled to -70 C. A solution of (S)-(5-oxotetrahydrofuran-3-yl)carbamic acid tert-butyl ester (289 mg, 1.4 mmol) in tetrahydrofuran (1 mL) was slowly added dropwise to the above reaction system, and the obtained mixture was stirred for 30 minutes. A white solid is formed. Then, a solution of the compound Ia-5 (280 mg, 0.72 mmol) in tetrahydrofuran (1 mL) was slowly added dropwise to the above reaction system. The resulting mixture was stirred at -40 C for 30 minutes. The reaction system was quenched with saturated aqueous sodium hydrogen sulfate and extracted with EtOAc. Separating organic phase, there isThe machine phase is dried over anhydrous sodium sulfate, filtered and concentrated.Rapid column chromatography (petroleum ether/ethyl acetate = 4/1)Purification afforded compound 4-6 (370 mg, yield: 87%) as a colourless oil.

104227-71-6, The synthetic route of 104227-71-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Shanghai Dinuo Pharmaceutical Technology Co., Ltd.; Gao Daxin; Chen Shoujun; Liu Fengtao; (47 pag.)CN108148022; (2018); A;,
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 26 1-(6-{[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]oxy}pyrimidin-4-yl)-N-(tetrahydrofuran-3-yl)-2,3-dihydro-1H-indole-5-carboxamide; [Show Image] To a mixture of 1-(6-{[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]oxy}pyrimidin-4-yl)-2,3-dihydro-1H-indole-5-carboxylic acid (150 mg) obtained in the below-mentioned Example 75, 3-aminotetrahydrofuran (42.9 muL), and N,N-dimethylformamide (10 mL) were added O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (192 mg) and N-ethyldiisopropylamine (87.8 muL), and the mixture was stirred at room temperature for 1 day. Water was added to the reaction mixture, and the mixture was extracted with a mixed solution of ethyl acetate and tetrahydrofuran. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with 50percent ethyl acetate/hexane to give the title compound (150 mg,87percent) as a white solid. 1H-NMR (300 MHz, CDCl3)delta:1.20 (t, J=7.6 Hz, 3 H), 1.72 – 2.00 (m, 3 H), 2.04 – 2.16 (m, 2 H), 2.29 – 2.43 (m, 1 H), 2.47 (q, J=7.6 Hz, 2 H), 3.27 (t, J=8.5 Hz, 2 H), 3.50 – 3.64 (m, 2 H), 3.76 – 3.96 (m, 3 H), 3.97 – 4.07 (m, 3 H), 4.23 – 4.35 (m, 2 H), 4.67 – 4.80 (m, 1 H), 5.34 – 5.46 (m, 1 H), 5.97 (s, 1 H), 6.19 (d, J=7.2 Hz, 1 H), 7.58 (dd, J=8.5, 1.5 Hz, 1 H), 7.65 (d, J=1.5 Hz, 1 H), 8.19 (s, 2 H), 8.41 (d, J=8.5 Hz, 1 H), 8.51 (s, 1 H).

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

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP2399914; (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.16874-33-2,Tetrahydrofuran-2-carboxylic acid,as a common compound, the synthetic route is as follows.

EXAMPLE 5; [00113] Preparation of Alfuzosin[00114] To a solution of tetrahydrofuroic acid (5.97 g) in methylene chloride (100 ml) was added thionyl chloride (3.75 ml). After 30 minutes of stirring, N-(4-amino-6,7- dimethoxy-2-quinaaolinyl)-N-methyl-l,3-propanediamine (10.0 g) was added and charged to the reaction mass. To this reaction mass was added triethyl amine, and maintained for about 90 minutes to about 105 minutes. On completion of the reaction as determined by TLC, the reaction mass was filtered to separate the insoluble triethylamine (“TEA”) hydrochloride and the solvent was evaporated at a temperature ranging from about 400C to about 45C under vacuum, to obtain gummy mass. To the gummy mass, isopropyl alcohol (50 ml) was charged and heated to a temperature ranging from about 550C to about 600C and stirred at the same temperature for about 30 to about 35 minutes. The mass was cooled to room temperature. The product was isolated by filtration, washed with isopropyl alcohol (10.0 ml). Wet product was dried at a temperature ranging from about 500C to about 55C to obtained crude alfuzosin (7.8gm). [00115] Purity( by HPLC): Greater than 99.6%, 16874-33-2

The synthetic route of 16874-33-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLENMARK PHARMACEUTICALS LIMITED; WO2006/90268; (2006); A2;,
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

A solution of 3-[4-(4-methylpiperazin-1-yl)phenyl]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,5-dihydro-6H-pyrazolo[4,3-c]pyridin-6-one (15.0 mg, 0.034 mmol, Example 1, Step 3), iodocyclohexane (7.2 mg, 0.034 mmol) and cesium carbonate (33.4 mg, 0.102 mmol) in N,N-dimethylformamide (2.0 mL) was stirred at 80 C. for 18 h. After cooling to room temperature, the mixture was concentrated in vacuo. The crude mixture was then dissolved in DCM (2.0 mL) and TFA (2.0 mL) was added dropwise at room temperature. After stirring for 2 h, the mixture was concentrated in vacuo. The crude mixture was dissolved in MeOH (3.5 mL) and 10% aqueous NH4OH (1.5 mL) was added. The mixture was purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min) to give the desired product. LCMS calculated for C23H30N5O (M+H)+: m/z=392.2; Found: 392.3. This compound was prepared according to the procedures described in Example 9, using 3-bromotetrahydrofuran instead of iodocyclohexane as starting material. LCMS calculated for C21H26N5O2 (M+H)+: m/z=380.2; Found: 380.3., 19311-37-6

19311-37-6 3-Bromotetrahydrofuran 12929516, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; Incyte Corporation; Ye, Qinda; Liu, Kai; Pan, Jun; Sokolsky, Alexander; Vechorkin, Oleg; Yao, Wenqing; (40 pag.)US2018/72719; (2018); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

5061-21-2, 2-Bromo-4-butanolide is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[Example 42]; Production of 2-mercapto-4-butyrolactone (using Na2S); 144 g (0.6 mol) of sodium sulfide nonahydrate (manufactured by JUNSEI CHEMICAL Co., Ltd.) were dissolved in a mixed solvent of 34 g of 1, 2-dimethoxyethane (Guaranteed Reagent; manufactured by JUNSEI CHEMICAL Co., Ltd.) and 34 g of purified water (which had been distilled and passed through an ion exchange filter) at room temperature. While theresultant solution was cooled with ice (to 100C or less) and under normal pressure (about 0.10MPa), 79 g of hydrochloric acid (GUARANTEED REAGENT, 35% to 37%; manufactured by JUNSEI CHEMICAL Co., Ltd.) were added with stirring the solution to adjust the pH of the solution to 8.9. While cooling thesolution to maintain the temperature of the solution at 100C or less, 34 g (0.2 mol) of 2-bromo-4-butyrolactone (manufactured by Tokyo Chemical Industry Co. , Ltd. ) were added dropwise into the solution over approximately 20 minutes. The reaction solution after the completion of the dropwise addition was stirred for 2 minutes. The pH of the reaction solution was within the range of 7.5 to 8.9 from when the dropwise addition of 2-bromo-4-butyrolactone was initiated to the stirring after the dropwise addition was completed.Thereafter, while cooling the solution to 100C or less, 24 g of hydrochloric acid were added to the solution over approximately 5 minutes to adjust the pH of the solution to 4.0. An inorganic salt deposited in the solution was removed by suction-filtration, and 20 g of ethyl acetate (Guaranteed Reagent; manufactured by JUNSEI CHEMICAL Co. , Ltd. ) were added to the resultant filtrate to extract the organic phase. The resultant aqueous phase was reextracted with 34 g of ethyl acetate. These extracted organic phases were combined and the resultant organic phase was concentrated and purified by distillation under a reduced pressure to give 17 g of2-mercapto-4-butyrolactone (having a boiling point of 94C/0.3 kPa; with a yield of 72%) .

5061-21-2, As the paragraph descriping shows that 5061-21-2 is playing an increasingly important role.

Reference£º
Patent; SHOWA DENKO K.K.; WO2007/139215; (2007); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem