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 29 (0340) 5-(4-Methoxymethyl-2,3,5,6-tetrafluorobenzyl)oxymethy lisoxazole-3-carboxylic acid (0.20 g, 0.6 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (0.10 g, 0.9 mmol), triethylamine (0.07 g, 0.7 mmol) and 1-hydroxybenzotriazole (0.01 g, 0.07 mmol) were added to chloroform (amylene addition product) (2 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.13 g, 0.7 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 0.12 g of N-(tetrahydrofuran-3-ylmethyl)-5-(4-methoxymethyl-2,3,5,6-t etrafluorobenzyl)oxymethylisoxazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (29)) represented by the following formula. 1H-NMR (CDCl3, TMS, delta(ppm)):1.63-1.68(1H, m), 2.03-2.12(1H, m), 2.51-2.61(1H, m), 3.39(3H, s), 3.45(2H, t), 3.58(1H, dd), 3.75(1H, dd), 3.83-3.85(1H, m), 3.89-3.91(1H, m), 4.57(2H, t), 4.68(2H, s), 4.71(2H, t), 6.74(1H, s), 6.94(1H, br s), 184950-35-4

As the paragraph descriping shows that 184950-35-4 is playing an increasingly important role.

Reference£º
Patent; Sumitomo Chemical Company, Limited; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

88675-24-5,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.

a) A solution of TETRAHYDROFURAN-3-AMINE (see W098/08855, 0.500 g, 4.04 mmol) and sodium acetate (0.331 g, 4.04 mmol) in a 1: 3 mixture of methanol and tetrahydrofuran (60 ml) was stirred at room temperature. To this was added (tert-butyl- dimethylsilanyloxy) acetaldehyde (2.112 g, 12.12 mmol) followed by glacial acetic acid (1.456 g, 24.24 mmol) and then sodium triacetoxyborohydride (2.568 g, 12. 12 mmol) was then added in 5 portions over 3 minutes (CAUTION: vigorous effervescence) and the resulting suspension was left to stir at room temperature for 4 hours. The mixture was evaporated under reduced pressure to leave a thick brown paste which was dissolved in dichloromethane (20 ml) and to this was added a solution of ammonia in methanol (7M solution, 25 ml). The mixture was stirred for 10 minutes and then evaporated under reduced pressure to leave an orange paste which was triturated with dichloromethane (50 ml) and filtered through Celite. The mixture was evaporated under reduced pressure to leave a brown gum which was dissolved in methyl tert-butyl ether (3 ML) and then purified by silica gel chromatography using methyl tert-butyl ether as eluent to give N-(2-{ [TERT- butyl (dimethyl) silyl] oxy} ethyl) tetrahydrofuran-3-amine (0.446 g, 48percent yield) as a brown oil: 1H-NMR (CDC13) : 3. 68 (8H, m), 2. 68 (2H, m), 2.04 (1H, m), 1.73 (1H, m), 0. 82 (9H, s), 0.00 (6H, s).

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

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/94410; (2004); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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

Example 89 Synthesis of (R)-4-amino-N-[4-(methoxymethyl)phenyl]-7-(1-methylcyclopropyl)-6-((tetrahydrofuran-2-yl)methoxy)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide 721 muL of (R)-(-)-tetrahydrofurfuryl alcohol was added to a suspension of 371 mg of sodium hydride (60%) in 15 mL of DMF with stirring at ice cooling temperature. The mixture was then stirred at room temperature for 30 minutes. A solution of 800 mg of 4-amino-6-bromo-N-[4-(methoxymethyl)phenyl]-7-(1-methylcyclopropyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide shown in Example 55 in 5 mL of DMF was added to the mixture, and stirred at 80 C. overnight. After cooling, the reaction mixture was partitioned between ethyl acetate and water, and the organic layer was washed with water and a saturated aqueous sodium chloride solution, followed by drying over sodium sulfate and solvent removal. The residue was purified by silica gel column (ethyl acetate/methanol=1/0->8/1), thereby obtaining 644 mg of the title compound., 97-99-4

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

Reference£º
Patent; TAIHO PHARMACEUTICAL CO., LTD.; MIYAZAKI, Isao; SHIMAMURA, Tadashi; KATO, Masanori; FUJITA, Hidenori; IGUCHI, Satoru; (161 pag.)US2018/9818; (2018); 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

5- (2-bromobenzyloxymethyl) isoxazole-3-carboxylic acid (0.94 g, 3.0 mmol), Tetrahydrofuran-3-ylmethylamine hydrochloride (0.62 g, 4.5 mmol), Triethylamine (0.46 g, 4.5 mmol) And 1-hydroxybenzotriazole (0.04 g, 0.3 mmol) Was added to chloroform (amylene added product) (7.5 mL). To the mixture, 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.69 g, 3.6 mmol) was added at room temperature, Stir overnight And then concentrated under reduced pressure. Dilute hydrochloric acid was added to the residue, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain N- (tetrahydrofuran-3-ylmethyl) -5- (2-bromobenzyloxymethyl) isoxazole-3-carboxamide (hereinafter referred to as present amide compound (265) ) 0.23 g was obtained., 184950-35-4

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

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

Production Example 148 (0468) Tetrahydrofuran-3-ylmethylamine hydrochloride (250 mg, 1.82 mmol) and a 1 mol/L aqueous sodium hydroxide solution (20 mL) were simultaneously added to a toluene solution (20 mL) of 5-(1-phenylcyclopropyl)isoxazole-3-carboxylic acid chloride (< 1.83 mmol), under ice-water cooling. The mixture was vigorously stirred for 30 minutes under ice-water cooling, and then the reaction 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 504 mg of N-(tetrahydrofuran-3-ylmethyl)-5-(1-phenylcyclopropyl)isoxa zole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (156)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)):1.41-1.46(m, 2H), 1.60-1.70(m, 3H), 2.01-2.11(m, 1H), 2.49-2.59(m, 1H), 3.39-3.44(m, 2H), 3.56(dd, J=8.9, 5.3Hz, 1H), 3.71-3.78(m, 1H), 3.80-3.92(m, 2H), 6.13(s, 1H), 6.86(brs, 1H), 7.29-7.42(m, 5H), 184950-35-4

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

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.4100-80-5,3-Methyldihydrofuran-2,5-dione,as a common compound, the synthetic route is as follows.

5,6-Diamino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (7.46 g, 43.82 mmol) and 3-methyldihydrofuran-2,5-dione (5.0 g, 43.82 mmol) were combined in DMF (15 mL). The reaction was stirred at room temperature for 30 min then ethyl acetate (150 mL) was added. The tan solid that precipitated was collected and washed with ethyl acetate (2*50 mL) and high vacuum dried for 6 h to give a mixture of 4-((6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)amino)-3-methyl-4-oxobutanoic acid and 4-((6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)amino)-2-methyl-4-oxobutanoic acid (10.1 g, 81percent yield) as a tan solid that were used without purification. A mixture of 4-((6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)amino)-3-methyl-4-oxobutanoic acid and 4-((6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)amino)-2-methyl-4-oxobutanoic acid (2.0 g, 7.04 mmol) were dissolved in 2N sodium hydroxide (18 mL) and heated at 85¡ã C. for 3 h. The reaction was cooled in an ice bath and 2N HCl was added until pH=2. Then 2 N sodium hydroxide was added to bring the mixture to pH to 6. The reaction was concentrated under reduced pressure. The residues were diluted with ethanol (100 mL) and filtered. The filtrate containing a mixture of 3-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-2-methylpropanoic acid and 3-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)butanoic acid was used directly in the next step.

4100-80-5, As the paragraph descriping shows that 4100-80-5 is playing an increasingly important role.

Reference£º
Patent; HYDRA BIOSCIENCES, INC.; Chenard, Bertrand L.; Gallaschun, Randall J.; Kimball, Spencer David; US2014/275528; (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- {3- [5- (2,2-difluoro-1,3-benzodioxolanyl)] propyl} isoxazole-3-carboxylic acid (0.58 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) 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- [5- (2,2-difluoro-1,3-benzodioxolanyl) propyl] isoxazole-3-carboxamide (Hereinafter referred to as present amide compound (231)) 0.57 g was obtained.

184950-35-4, As the paragraph descriping shows that 184950-35-4 is playing an increasingly important role.

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.184950-35-4,(Tetrahydrofuran-3-yl)methanamine hydrochloride,as a common compound, the synthetic route is as follows.

1-butyl-1 H-pyrazole-3-carboxylic acid (0.82 g, 4.8 mmol), Tetrahydrofuran-3-ylmethylamine hydrochloride (0.66 g, 4.8 mmol), Triethylamine (0.48 g, 4.8 mmol) And 1-hydroxybenzotriazole (0.07 g, 0.48 mmol) Was added to chloroform (amylene addition product) (30 mL). To the mixture, 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.92 g, 4.8 mmol) was added at room temperature, After stirring overnight at room temperature, it was 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 over 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) -1-butyl-1 H-pyrazole-3-carboxamide (hereinafter referred to as the present amide compound (8)) 0.86 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

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.

4-Bromo-2-fluoro-bezonitrile (1.25 g), (S)-tetrahydro-furan-3-ylamine hydrochloride (0.785 g), and DIPEA (2.4 mL) are dissolved in DMSO (20 mL) and stirred at room temperature overnight. The reaction mixture is poured into saturated aqueous NH4Cl (150 mL), extracted with EtOAc (3¡Á100 mL), dried over Na2SO4, filtered, and concentrated to give (S)-4-bromo-2-(tetrahydrofuran-3-ylamino)benzonitrile (1.6 g, 96% yield). LCMS: m/z=267, 269 [M+H]+., 204512-95-8

204512-95-8 (S)-Tetrahydrofuran-3-amine hydrochloride 18664284, aTetrahydrofurans compound, is more and more widely used in various fields.

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

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- (3,4-difluorobenzyloxymethyl) isoxazole-3-carboxylic acid (0.54 g, 2.0 mmol), Tetrahydrofuran-3-ylmethylamine hydrochloride (0.41 g, 3.0 mmol), Triethylamine (0.30 g, 3.0 mmol) And 1 – hydroxybenzotriazole (0.03 g, 0.2 mmol) Was added to chloroform (amylen 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 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- (3,4-difluorobenzyloxymethyl) isoxazole-3-carboxamide (Hereinafter referred to as present amide compound (263)) 0.36 g was obtained

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

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; SUMITA, YUSUKE; (264 pag.)JP2015/51963; (2015); A;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem