Heterocyclic Building Blocks-Tetrahydrofuran

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 1 (0210) (Tetrahydrofuran-3-yl)methylamine hydrochloride (240 mg) and a 1 mol/L aqueous sodium hydroxide solution (5 mL) were simultaneously added to a solution of 5-(1-naphthyloxymethyl) pyridine-2-carboxylic acid chloride (<0.68 mmol) in toluene (10 mL) obtained in Reference Production Example 4, and the mixture was vigorously stirred at room temperature for 20 minutes, and then extracted with ethyl acetate. The organic layer was sequentially washed with 1 mol/L hydrochloric acid and a saturated saline solution, then dried over sodium sulfate, and concentrated under reduced pressure conditions. The residue was applied to a silica gel column chromatography to obtain 208 mg of N-(tetrahydrofuran-3-ylmethyl)-5-(1-naphthyloxymethyl)pyrid ine-2-carboxylic acid amide (hereinafter, referred to as Compound of the Present Invention (1).) represented by the following formula. Compound of the Present Invention (1) (0211) 1H-NMR (CDCl3, TMS) delta(ppm): 1.68-1.78 (m, 1H), 2.06-2.16 (m, 1H), 2.59-2.68 (m, 1H), 3.50-3.55 (m, 2H), 3.61-3.67 (m, 1H), 3.75-3.82 (m, 1H), 3.87-3.96 (m, 2H), 5.35 (s, 2H), 6.87-6.91 (m, 1H), 7.36-7.41 (m, 1H), 7.48-7.55 (m, 3H), 7.81-7.85 (m, 1H), 8.02-8.05 (m, 1H), 8.21 (br s, 1H), 8.25-8.32 (m, 2H), 8.72-8.7 5(m, 1H). As the paragraph descriping shows that 184950-35-4 is playing an increasingly important role. Reference£º
Patent; Sumitomo Chemical Company, Limited; AWASAGUCHI, Kenichiro; (20 pag.)US2017/144995; (2017); 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.112372-15-3,Furo[2,3-c]pyridine-2-carboxylic acid,as a common compound, the synthetic route is as follows.

Step 6. A solution of furo[2,3-c]pyndine-2-carboxylic acid (35 mg, 0.21 mmol, 1 . 10 equiv), [5-(oxane-4-sulfonyl)pyridin-2-yl]methanamine (50 mg, 0.20 mmol, 1 00 equiv). EDC1 (74.6 mg, 0 39 mmol, 1 .99 equiv), tricthylamine (59 2 mg, 0 59 mmol, 3.00 equiv), and HOBt (31 6 mg, 0.23 mmol, 1 .20 equiv) in DMF (5 mL) was stirred overnight at rt. The reaction mixture was diluted with 50 mL of water The resulting solution was extracted with 3×50 mL of ethyl acetate. The combined organic layers was washed with 3×100 mL of brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified on a silica gel column eluted with dichloromethane/methanol (80: 1 to 40: 1 ) to give 3.3 mg (4%) of the title compound as an off-white solid. 1HNMR (300 MHz, CD3OD) delta 8.99-8.97 (m, 2H), 8.47-8.45 (d, = 5.4 Hz, 1H), 8.27-8.24 (dd, = 2.4, 8.4 Hz, 1H), 7.86-7.84 (dd, J = 0.9, 5.4 Hz, 1H), 7.72-7.69 (d, J = 8.4 Hz, 1H), 7.63 (s, HI), 4.03 -3.98 (m, 2H), 3 54-3 37 (m, 5H), 1 88- 1 66 (m, 4H) LC MS (Method A, ESI): RT = 1.22 min, m/z = 402.0 [M+H] .

112372-15-3 Furo[2,3-c]pyridine-2-carboxylic acid 13803072, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; GENENTECH, INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; DRAGOVICH, Peter; GOSSELIN, Francis; YUEN, Po-Wai; ZAK, Mark; ZHENG, Xiaozhang; WO2013/127267; (2013); 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.

To a mixture of 2-tetrahydrofuroic acid (288 mL, 3 mmol) in chloroform (5 mL) was added thionyl chloride (660 muL, 9 mmol) and the reaction heated to reflux for 1 hour. The reaction was cooled and concentrated under reduced pressure to provide tetrahydro-furan-2-carbonyl chloride (405 mg, 3 mmol).

16874-33-2 Tetrahydrofuran-2-carboxylic acid 86079, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; WYETH; WO2008/73929; (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.97-99-4,(Tetrahydrofuran-2-yl)methanol,as a common compound, the synthetic route is as follows.

Example 11A (2R)-tetrahydrofuran-2-ylmethyl 4-methylbenzenesulfonate To (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) portion-wise over 5 minutes. This mixture was stirred for 16 hours at ambient temperature then was quenched with 10 mL of 5% aqueous HCl and was extracted with 3*5 mL CH2Cl2. The combined organics were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (SiO2, 75% hexanes in ethyl acetate) to give the title compound (1.7 g, 6.8 mmol, 69% yield). MS (DCI/NH3) m/z 257 (M+H)+ and 274 (M+NH4)+.

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

Reference£º
Patent; ABBOTT LABORATORIES; US2009/105306; (2009); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

17347-61-4, 2,2-Dimethylsuccinicanhydride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 1-[2-(4-amino-phenyl)-5-tert-butyl-2H-pyrazol-3-yl]-3-[4-(pyridin- 4-yloxy) -phenyl]-urea (208 mg, 0.47 mmol) and 2,2-dimethylsuccinic anhydride (66 mg, 0.52 mmol, 1.1 eq) in 2 mL THF was stirred at room temperature overnight. HPLC analysis indicated that starting material was remaining. The reaction was then heated at 60¡ãC for 2 days, at which time HPLC analysis indicated the reaction was complete. The reaction mixture was cooled to room temperature, and the resulting suspension was diluted with Et20. The solid was isolated by filtration to afford the desired product (227 mg, 85percent). (at)H-NMR (DMSO-d6) 8 12.06 (s, 1 H), 10.06 (s, 1 H), 9.09 (s, 1 H), 8.40 (d, J = 6.0 Hz, 2H), 8.31 (s, 1 H), 7.69 (d, J = 9.0 Hz, 2H), 7.47 (d, J = 9.0 Hz, 2H), 7.39 (d, J = 9.0 Hz, 2H), 7.07 (d, J = 9.0 Hz, 2H), 6.85 (dd, J = 1.5 4.7 Hz, 2H), 6.33 (s, 1 H), 2.59 (s, 2H), 1.26 (s, 9H), 1.21 (s, 6H) ; MS LC-MS [M+H] (at) = 571.3, RT = 2.49 min.

17347-61-4 2,2-Dimethylsuccinicanhydride 87067, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; BAYER PHARMACUETICALS CORPORATION; WO2005/110994; (2005); A2;,
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

General procedure: A solution of 13 (0.06 mmol) with DMAP (1 equiv) and an appropriate acid anhydride (10 equiv) in anhydrous pyridine(10 ml) was stirred at 155 C for 2 h in a microwave oven (Biotage). The reaction mixture was diluted with EtOAc and neutralized with HCl (1 N) and then extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuum to afford the crude product, followed by chromatographyon a silica gel column and recrystallization to give13e-m.

4100-80-5 3-Methyldihydrofuran-2,5-dione 20051, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Article; Wu, Haifeng; Ma, Guoxu; Yang, Qinwen; Zhu, Yindi; Huang, Li; Tian, Yu; Yang, Xiaoming; Zhang, Menghan; Chen, Chin-Ho; Morris-Natschke, Susan L.; Yang, Meihua; Xu, Xudong; Lee, Kuo-Hsiung; European Journal of Medicinal Chemistry; vol. 166; (2019); p. 159 – 166;,
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- (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) Was added to chloroform (amylene 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 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- (3-phenylpropyl) isoxazole-3-carboxamide (Hereinafter referred to as amide compound (22)) 0.49 g.

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

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-fluoro-4-methoxybenzyloxymethyl) isoxazole-3-carboxylic acid (1.10 g, 3.9 mmol), Tetrahydrofuran-3-ylmethylamine hydrochloride (0.81 g, 5.9 mmol), Triethylamine (0.82 mL, 5.9 mmol) And 1-hydroxybenzotriazole (0.05 g, 0.4 mmol) Was added to chloroform (amylene added product) (10 mL). To the mixture, 1 – ethyl – 3- (3 – dimethylaminopropyl) carbodiimide hydrochloride (0.90 g, 4.7 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-fluoro-4-methoxyxybenzyloxymethyl) isoxazole-3-carboxamide (Hereinafter referred to as present amide compound (277)) 0.38 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.165253-31-6,(Tetrahydrofuran-3-yl)methanamine,as a common compound, the synthetic route is as follows.

A 0.5-2 mL microwave vial containing a stir bar was placed under argon by attaching a rubber septum and performing 4 vacuum/argon cycles. The intermediate from Example 9 Step C (100 mg, 0.146 mmol), sodium tert-butoxide (20.99 mg, 0.218 mmol), 2-(di- tert-butylphosphino)biphenyl (8.7 mg, 0.029 mmol), Pd2(dba)3 (13.33 mg, 0.015 mmol) were added, and the vial was sealed. While adding the solids to the vial, 30 mL of toluene was deoxygenated by bubbling argon through for 30 minutes; 1.0 mL of this was added to the sealed reaction vial. 3-(Aminomethyl)tetrahydrofuran (0.024 ml, 0.204 mmol) was added via microsyringe, and men argon was flushed gently through the vial for 5 min. The reaction was heated to 90C for 15 hours and then cooled to room temperature. A solution of tetrabutylammonium fluoride (1 M in tetrahydrofuran, 0.710 ml, 0.710 mmol) was added, and the vial was heated in a microwave oven for 10 min at 1500C. After cooling to room, temperature, the reaction mixture was partitioned between a 1 :1 mixture of EtOAc: ether (20 mL) and water (10 mL). The layers were separated, and the organic layer was washed sequentially with water (10 mL), saturated NaHCtheta3 (10 mL), and brine (10 mL), dried over Na2SO4, filtered, and concentrated. The resulting solid was purified by reverse phase HPLC. After lypophilization, the title compound was obtained. 1H NMR (600 MHz, DMSO) delta: 11.44 (s, 1 H), 9.57 (s, 1 H), 8.22 (m, 1 H), 7.68 (m, 1 H), 7.49 (t, 1 H, J= 6.3 Hz), 7.38 (t, 2 H, J= 8.2 Hz), 7.16 (d, 2 H, J= 5.6 Hz), 3.78 (m, 2 H), 3.64 (q, 1 H, J= 7.6 Hz), 3.51 (dd, 1 H, J= 8.5, 5.6 Hz), 3.17 (m, 2 H), 2.60 (m, 1 H), 2.04 (m, 1 H), 1.66 (m, 1 H): [M+l]+ 447.

165253-31-6 (Tetrahydrofuran-3-yl)methanamine 10898660, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; MERCK & CO., INC.; WO2007/145957; (2007); A1;,
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 139 (0459) 5-(4-Phenoxybutyl)isoxazole-3-carboxylic acid (0.52 g, 2.0 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (0.33 g, 2.4 mmol), triethylamine (0.25 g, 2.4 mmol) and 1-hydroxybenzotriazole (0.03 g, 0.24 mmol) were added to chloroform (amylene addition product) (5 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.46g, 2. 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 0.51 g of N-(tetrahydrofuran-3-ylmethyl)-5-(4-phenoxybutyl)isoxazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (146)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)):1.66-1.69(1H, m), 1.83-1.98(4H, m), 2.08-2.11(1H, m), 2.54-2.61(1H, m), 2.89(2H, t), 3.44-3.47(2H, m), 3.59(1H, dd), 3.77(1H, dd), 3.84-3. 94 (2H, m), 3.99(2H, t), 6.48(1H, s), 6.89(2H, ddd), 6.95(2H, dq), 7.27-7.31(2H, m)

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