Category: Tetrahydrofurans

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.

Production Example 252 (0573) 5-(3-Chloro-4-fluorobenzyloxymethyl)isoxazole-3-carbo xylic 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) were added to chloroform (amylene addition product) (20 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (2. 05 g, 10.7 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 residue, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated saline water and dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 0.29 g of N-(tetrahydrofuran-3-ylmethyl)-5-(3-chloro-4-fluorobenzylox ymethyl)isoxazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (261)) represented by the following formula. 1H-NMR (CDCl3, TMS, delta (ppm)) : 1.62-1.73 (1H, m), 2.04-2.15 (1H, m), 2.53-2.63 (1H, m), 3.47(2H, t), 3.59 (1H, dd), 3.73-3.80 (1H, m), 3.84-3.95(2H, m), 4.54(2H, s), 4.66(2H, s), 6.73(1H, s), 6.93(1H, br s), 7.13(1H, t), 7.18-7.24(1H, m), 7.40(1H, dd), 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

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.

97-99-4, To a mixture of (R)-(tetrahydrofuran-2-yl)methanol (Fluka, 4.0 g, 39.2 mmol) and di-tert-butyl hydrazine-1,2-dicarboxylate (9.1 g, 39.2 mmol) in THF (50 mL) was added triphenylphosphine (14.4 g, 54.8 mmol) followed by (E)-di-tert-butyl diazene-1,2-dicarboxylate (12.6 g, 54.8 mmol), portionwise. This mixture was stirred at ambient temperature for 16 h then was concentrated under reduced pressure and purified by column chromatography (SiO2, 99% hexane/EtOAc to 25% hexane/EtOAc) to give the title compound (11.8 g, 37.3 mmol, 95% yield). MS (DCI/NH3) m/z 317 (M+H)+

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

Reference£º
Patent; ABBOTT LABORATORIES; US2010/69348; (2010); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

124391-75-9, (S)-(Tetrahydrofuran-3-yl)methanol is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(1) a chloroform solution (100 mL) of tetrahydrofuran-3-ylmethanol (5.1 g), at room temperature, triethylamine (13.8 mL), trimethylamine hydrochloride (1.43 g), p-toluenesulfonyl chloride (11.4 g ), and the mixture was stirred for 14 hours. The reaction mixture was washed with saturated brine, and the organic layer was dried over anhydrous magnesium sulfate.After filtration over anhydrous magnesium sulfate, and N, and N- dimethylformamide (100 mL) was added a solution under reduced pressure the solvent was distilled off the resulting residue was (14.2 g). Then potassium carbonate (13.8 g), and stirred for 2 hours 30 minutes at 65 C. was added 2-mercaptobenzothiazole and (10.0g).Distilled water was added to the reaction mixture and extracted with ethyl acetate.The organic layer was washed with saturated brine, and dried with anhydrous magnesium sulfate.After filtration over anhydrous magnesium sulfate, toluene under azeotropic vacuo, and evaporated to give a residue (10.4 g). It was dissolved adding chloroform (75mL), under ice-cooling, and the mixture was stirred for 18 hours added m- chloroperbenzoic acid (24.9g). After stirring added a saturated aqueous sodium thiosulfate solution and saturated aqueous sodium bicarbonate sulfate, and extracted with chloroform. The organic layer was concentrated under reduced pressure 2- (tetrahydrofuran-3-yl-methyl-sulfonyl) -1,3-benzothiazole (11.4 g) as a yellow oily substance.

124391-75-9, The synthetic route of 124391-75-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TAISHO PHARMACEUTICAL COMPANY LIMITED; NISSAN CHEMICAL INDUSTRIES LIMITED; KURODA, SHOICHI; USHIKI, YASUNOBU; KAWAGUCHI, TAKANORI; FUSEGI, KEIKO; BOHNO, MASAHIRO; IMAI, YUDAI; UNEUCHI, FUMITO; IWAKIRI, KANAKO; TANAKA, HIROAKI; BOHNO, AYAKO; CHONAN, TOMOMICHI; ITOH, SHIN; OTA, HIROFUMI; ISHIYAMA, SEISHI; OKADA, TAKUYA; SASAKO, SHIGETADA; MONMA, SOUICHI; NIWA, MARIE; OKADA, TAKUMI; (289 pag.)JP2015/231988; (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 116 (0432) Tetrahydrofuran-3-ylmethylamine hydrochloride (0.19 g, 1.13 mmol) and triethylamine (0.14 g, 1.36 mmol) were added to chloroform (amylene addition product) (8 mL). 5-(3-Benzyloxymethylbenzyloxymethyl)isoxazole-3-carboxylic acid (0.40 g, 1.22 mmol), 1-hydroxybenzotriazole (0.02 g, 0.11 mmol) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.26 g, 1.36 mmol) were added to the mixture at room temperature, and the mixture was stirred overnight. Then, dilute hydrochloric acid was added thereto, and the mixture was extracted twice with chloroform. The organic layer was washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 0.43 g of N-(tetrahydrofuran-3-ylmethyl)-5-(3-benzyloxymethylbenzylox ymethyl)isoxazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (121)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)): 1.62-1.70(1H, m), 2.02-2.11(1H, m), 2.51-2.62(1H, m), 3.43-3.47(2H, m), 3.56-3.60(1H, m), 3.72-3.78(1H, m), 3.82-3.93(2H, m), 4.56(2H, s), 4.57(2H, s), 4.60(2H, s), 4.64(2H, s), 6.73(1H, s), 7.07(1H, br s), 7.26-7.37(9H, m), 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.204512-95-8,(S)-Tetrahydrofuran-3-amine hydrochloride,as a common compound, the synthetic route is as follows.

Compound 6: (5VN-(4-fluoro-3-methylphenyl)-l -methyl-4-(2-oxo-2-(tetrahydrofuran-3- ylamino)acetyl)-lH-pyrrole-2-carboxamide 2-(5-(4-Fluoro-3-methylphenylcarbamoyl)-l -methyl- lH-pyrrol-3-yl)-2-oxoacetic acid (300 mg, 0.95 mmol), (S)-tetrahydrofuran-3 -amine hydrochloride (128 mg, 1.04 mmol) and N,N-diisopropylethylamine (DIPEA, 611 mg, 4.73 mmol) were dissolved in 5 mL of DMF under N2. 2-(7-Aza-lH-benzotriazole-l-yl)-l,l,3,3-tetramethyluronium hexafluoro- phosphate (HATU, 396 mg, 1.04 mmol) was added and the mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with 100 mL EtOAc and washed with IN HCI, NaHC03 solution, and brine. The organic layer was evaporated under reduced pressure. The residue was crystallized from a mixture of 10 mL MeOH and 5 mL water. The crystals were filtered off and dried in vacuum to provide ?5)-N-(4-fluoro-3-methylphenyl)-l- methyl-4-(2-oxo-2-(tetrahydrofuran-3-ylamino)acetyl)-lH-pyrrole-2-carboxamide (Compound 6, 248 mg) as a white powder, mp =155.7C. LC method B; Rt: 0.90 min. m/z : 372.2 (Mu-Eta)” Exact mass: 373.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.86 – 1.99 (m, 1 H), 2.07 – 2.18 (m, 1 H), 2.23 (d, J=1.8 Hz, 3 H), 3.57 (dd, J=8.9, 4.5 Hz, 1 H), 3.71 (td, J=8.1, 5.7 Hz, 1 H), 3.78 – 3.87 (m, 2 H), 3.95 (s, 3 H), 4.30 – 4.42 (m, 1 H), 7.09 (t, J=9.2 Hz, 1 H), 7.49 – 7.56 (m, 1 H), 7.62 (d, J=1.8 Hz, 1 H), 7.66 (dd, J=7.2, 2.3 Hz, 1 H), 8.11 (d, J=1.3 Hz, 1 H), 8.88 (d, J=6.8 Hz, 1 H), 10.05 (s, 1 H).

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

Reference£º
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; KESTELEYN, Bart, Rudolf, Romanie; PIETERS, Serge, Maria, Aloysius; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2015/11281; (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.124391-75-9,(S)-(Tetrahydrofuran-3-yl)methanol,as a common compound, the synthetic route is as follows.

REFERENCE EXAMPLE 6 Preparation of (tetrahydro-3-furanyl)methyl tosylate (Compound No. D5) A mixture comprising 50 g of (tetrahydro-3-furanyl)methanol, 95 g of tosyl chloride, 52 g of triethylamine and 450 ml of THF was refluxed for 8 hours. After separation of insolubles by filtration, the reaction fluid was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/7) to obtain 114.5 g of (tetrahydro-3-furanyl)methyl tosylate.

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; Mitsui Toatsu Chemicals, Inc.; US5434181; (1995); A;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

112372-15-3, Furo[2,3-c]pyridine-2-carboxylic acid is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of [5-[4-(pyrrolidin-1-yl)piperidine-l -sulfonyl]pyridin-2-yl]methanamine (72 mg, 022 mmol, 1.00 equiv), furo[2,3-c]pyridine-2-carboxylic acid (40 mg, 0,25 mmol, 1.10 equiv), EDCI (85 mg, 0.44 mmol, 2.00 equiv), HOBt (36 mg, 0.27 mmol, 1.20 equiv), and tnethylamine (67.3 mg, 0.67 mmol, 3.00 equiv) in DMF (10 mL) was stirred for 1.5 h at rt. The reaction was then quenched by the addition of 50 mL of water and the resulting solution was extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with 3×100 mL of brine, dried over anhydrous sodium sulfate, and then concentrated under vacuum. The residue was purified on a silica gel column eluted with dichloromethane/methanol (50: 1 to 20: 1 ) to give 143 mg ( 14%) of the title compound as a light yellow solid LC MS (Method H, F.SI): RT = 101 min, m z = 470.0 [M+H] ‘ . 1HNMR (400 MHz, DMSO-d6) 5969-9.65 (t, J = 6 Hz, 1H), 9.08 (s, 1H), 8.85-8.84 (d,J= 2.1 Hz, 1H), 8.50-8.48 (d,J = 5.1 Hz, 1H), 8.15-8.11 (dd, J= 2.4, 8.4 Hz, 1H), 7.85-7.83 (d, J=5.1 Hz, 1H), 7.69-7.62 (d, J = 8.1 Hz, 2H), 4.72- 4.70 (d, J = 60 Hz, 2H), 3.50-3.47 (d, J=96 Hz, 2H), 2.50-249 (m, 6H), 2.05-2.01 (m, 1H), 1.87-1.84 (d, J = 108Hz,2H), 1.62 (s,4H), 1.45-1.38 (m, 2H)., 112372-15-3

As the paragraph descriping shows that 112372-15-3 is playing an increasingly important role.

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

112372-15-3, Furo[2,3-c]pyridine-2-carboxylic acid is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a suspension of furo[2,3-c] pidine-2-carboxylic acid (0.030 g, 0.47 1 mmol), 5-((2- (pidin-3 -yl) phenoxy) methyl)-4, 5 -dihydroisoxazol-3 -yl) methanamine dihydrochloride (¡À) (0.050 g, 0.156 mmol) in N,N-dimethylformamide (2 mL) wasadded BOP reagent (0.076 g, 0.172 mmol) and N,N-diisopropylethylamine (0.200 mL,1.286 mmol) at -5C under nitrogen atmosphere. Reaction mixture was stirred at room temperature for 14 h. The reaction mixture was poured onto ice water, extracted with ethyl acetate (2 x 15 mL). The combined ethyl acetate layer was washed with water, brine solution (2 x 5 mL). The organic phase was dried over sodium sulfate and concentrated under reduced pressure to give a residue. The residue was purified bycolumn chromatography (methanolldichloromethane = 4/96) to give the titled compound(0.012 g, 21%) as a solid. HPLC: 94.23 %; LCMS: m/z 430.2 [M+2] 1H NMR (400MHz, Chloroform-d) 8.88 (s, 1H), 7.72 – 7.52 (m, 5H), 7.48 (s, 1H), 7.21 – 7.07 (m,3H), 6.76 (td, J= 7.5, 1.1 Hz, 1H), 6.67 (d, J= 8.1 Hz, 1H), 4.99 (ddt, J= 10.7, 7.3, 4.0Hz, 1H), 4.45 (dd, J = 17.2, 5.8 Hz, 1H), 4.32 (dd, J = 17.2, 5.3 Hz, 1H), 3.36 (dt, J =13.2, 3.8 Hz, 1H), 3.29- 3.15 (m, 2H), 2.94 (dd, J= 17.3, 6.7 Hz, 1H)., 112372-15-3

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

Reference£º
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; PANIGRAHI, Sunil Kumar; WO2014/111871; (2014); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

42417-39-0, 3-Aminodihydrofuran-2(3H)-one hydrochloride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To synthesize 3-oxo-phenylacyl homoserine lactones, 400 mg of PS-carbodiimide resin (Argonaut Technologies) (793.65 g/mol; 0.504 mmol; 2.0 mol equiv) was added to a 10 mL reactivial (Pierce). To the reactivial, phenylacylcarboxylic acid (1.0 mol equiv), 2,2-dimethyl-l,3-dioxane-4,6-dione (Meldrum’s acid; 1.0 mol equiv), and 4,4- dimethylarainopyridine (1.05 mol equiv) were added with ~5 mL dichloromethane. The reaction was allowed to stir overnight at room temperature. Upon completion, the resin was removed by filtration, and the solvents were evaporated. Product was redissolved in ethyl acetate and washed with 0. IN HCl. The organic layer was dried over magnesium sulfate, which was removed by filtration. The solvents were removed in vacuo and the final product was dissolved in ~5 mL acetonitrile and transferred to a 10 mL reactivial (Pierce). To the reactivial, ?-aminobutryolactone HCl (1.0 mol equiv) and triethylamine (1.2 mol equiv) were added. The reaction mixture was then irradiated by microwave for 10 min at IOOW twice. Upon completion of microwave reaction, solvents were removed in vacuo. Crude product was redissolved in ethyl acetate with minimal water to aid solubility and washed once each with saturated Sodium bicarbonate, IM Potassium bisulfate, and saturated Sodium Chloride. The organic layer was dried over magnesium sulfate, which was removed by filtration. Solvents were removed in vacuo and the resulting product was redissolved in a minimal volume of ethyl acetate and loaded onto a 2Og flash chromatography column. The final product was purified by flash chromatography (Flashmaster system; Argonaut Technologies) using the gradient system shown in Table 1. Table 1.Fractions were collected and analyzed by thin layer chromatography (80:20 Ethyl acetate/hexanes). Fractions containing product were collected and solvents were removed in vacuo. The final product was confirmed by H-NMR and mass spectrometry (H-NMR results presented in Example 14).

42417-39-0, The synthetic route of 42417-39-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; HEALTH RESEARCH INC.; DOLNICK, Bruce, J.; WO2006/110531; (2006); A2;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

118399-28-3, (R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(R)-Benzyl 5-oxotetrahydrofuran-3-ylcarbamate (INTERMEDIATE 3, 27.0 g, 114.78 mmol) was dissolved in methanol (75 ml) and triethylamine (75 ml) was added at room temperature. The resulting mixture was allowed to stir overnight at this temperature. The mixture was concentrated in vacuo to provide the title product. This material was used to prepare INTERMEDIATE 5 without further purification.1H NMR (300 MHz, CHLOROFORM-d) delta ppm 2.67 (d, 2H) 3.60-3.72 (m, 3H) 3.70-3.78 (m, 1H) 4.00-4.15 (m, 2H) 5.03-5.18 (m, 2H) 5.52 (br. s., 1H) 7.28-7.42 (m, 5H).

118399-28-3, 118399-28-3 (R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate 697924, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; US2012/35134; (2012); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem