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 9 (0320) 1-Benzyl-1H-1,2,3-triazole-4-carboxylic acid (0.96 g, 4.7 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (0.71 g, 5.2 mmol), triethylamine (1.01 g, 10 mmol) and 1-hydroxybenzotriazole (0.08 g, 0.52 mmol) were added to chloroform (amylene addition product) (30 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (1.00 g, 4.2 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 0.86 g of 31-benzyl-1H-1,2,3-triazole-4-carboxamide (hereinafter, referred to as Compound of Present Invention (9)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)): 1. 6.4-1 . 72 (1H, m), 2.03-2.11(1H, m), 2.54-2.59(1H, m), 3.46(2H, dd), 3.58(1H, dd), 3.75(1H, q), 3.93-3.84(2H, m), 5.55(2H, s), 7.41-7.27(5H, m), 7.97(1H, s), 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;,
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111769-27-8, (R)-Tetrahydrofuran-3-amine 4-methylbenzenesulfonate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(b) To ethyl l-(6-chloro-l-(3,5-dimethylphenyl)-5-methyl-lH-benzo[d]imidazol-2-yl)piperidine- 4-carboxylate (8.6 mg) was added ethanol (2 mL) and aqueous sodium hydroxide (1 mL, 2 N). The reaction mixture was stirred at 4O0C for two hours, neutralized with aqueous hydrochloric acid (2 N) and concentrated in vacuo. The residue was mixed (R)-(+)-tetrahydrofuran-3 -amine A- methylbenzenesulfonate (6.3 mg, 0.024 mmol), 2-(7-aza-lH-benzotriazole-l-yl)-l, 1,3,3- tetramethyluronium hexafluorophosphate (HATU, 9.2 mg, 0.024 mmol), 7V,iV-diisopropyl- ethylamine (Hunig’s base, DIEA, 7.8 mg, 0.060 mmol) and N,N-dimethylformamide (5 mL) was stirred at room temperature over the weekend. The reaction mixure was concentrated in vacuo, the residue subjected to preperative hplc (Preparative RP-LC was performed on a Gilson system equipped with a Zorbax SB-C8 (5 mum, 21.2 x 150 mm) column, using methano I/water (0.05% formic acid) gradients at a flow rate of 15 mL/min with UV (214 or 254 nm) and MS (ESI) detection) to give 7.7 mg (82 % yield) (R)-l-(6-chloro-l-(3,5-dimethylphenyl)-5-methyl-lH- benzo[d]imidazol-2-yl)-N-(tetrahydrofuran-3-yl)piperidine-4-carboxamide. MS (m/z) 467.0 (M+l)., 111769-27-8

111769-27-8 (R)-Tetrahydrofuran-3-amine 4-methylbenzenesulfonate 14243169, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; NOVASAID AB; WANNBERG, Johan; ALTERMAN, Mathias; MALM, Johan; STENBERG, Patric; WESTMAN, Jacob; WALLBERG, Hans; WO2011/23812; (2011); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1679-47-6,3-Methyldihydrofuran-2(3H)-one,as a common compound, the synthetic route is as follows.

Example 11 Hydrogenation of alpha-methyl-gamma-butyrolactone [Ru2(mu-Cl)3(triphos)2]Cl (3.0 mg), potassium tert-butoxide (5.5 mg), and 1. 5 ml of methanol were added into a 20-ml Schlenk tube under a nitrogen atmosphere, and the mixture was stirred for 20 minutes at room temperature. This solution and alpha-methyl-gamma-butyrolactone (0.12 g) were added into a 100-ml autoclave having a stirrer placed inside, under a nitrogen atmosphere. The autoclave was purged with hydrogen, and then hydrogen was further included in the autoclave up to 4.0 MPa. The contents of the autoclave were heated and stirred at 100C for 13 hours. After cooling, the reaction liquid was analyzed by gas chromatography, and it was found that 1,4-pentanediol was produced at a yield of 39.7%., 1679-47-6

The synthetic route of 1679-47-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Takasago International Corporation; EP2141142; (2010); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17347-61-4,2,2-Dimethylsuccinicanhydride,as a common compound, the synthetic route is as follows.

Step E: Intermediate 26-2 To a solution of the intermediate 25-2 in pyridine (1 mL) were added DMAP (150 mg, 1.171 mmol) and 3, 3-dimethyldihydro-2,5-furandione (480 mg, 3.93 mmol). The reaction mixture was stirred at 80 ¡ãC for 1.5 h. After cooling down to room temperature, the reaction mixture was extracted with DCM (50 mL x 3). The organic phase was separated, washed with water, brine, and dried with Na2S04. Removal of the solvent provided a crude product, which was purified by column chromatography on silica gel (PE: EtOAc = 3:1 ) to afford the intermediate 26-2 (240 mg, 0.337 mmol, 70.3 percent yield) as a white solid.

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

Reference£º
Patent; GLAXOSMITHKLINE LLC; GAO, Daxin; HAN, Nianhe; JOHNS, Brian; JIN, Zhimin; NING, Fangxian; TANG, Jun; WU, Yongyong; YANG, Heping; WO2013/20245; (2013); A1;,
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17347-61-4, 2,2-Dimethylsuccinicanhydride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The compound 6 (349 mg, 0.5 mmol) is dissolved in anhydrous pyridine (8 ml) in, adding 2, 2 – dimethyl succinic anhydride (320 mg, 2.5 mmol), DMAP (61 mg, 0.5 mmol), after dissolving completely, microwave reactor is heated to 160 ¡ãC, reaction 3 h. The end of the reaction, by adding ethyl acetate (50 ml), for 10percent HCl to adjust the pH 4 – 5; organic layer is saturated salt water washing (25 ml ¡Á 3), dried with anhydrous sodium sulfate, filtered, concentrated under reduced pressure to remove the solvent, silica gel column chromatography (hexane: ethyl acetate=1:1), to obtain white solid 302 g, is compound 9, yield 73percent.

17347-61-4, As the paragraph descriping shows that 17347-61-4 is playing an increasingly important role.

Reference£º
Patent; Chen Zhong; Duan Huaqing; Yang Shilin; Li Guoxiong; (26 pag.)CN109485688; (2019); A;,
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16874-33-2, Tetrahydrofuran-2-carboxylic acid is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Add 2-(5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6- to a 50 mL two-necked vial Triamine (0.10 g, 0.27 mmol),Tetrahydrofuran-2-carboxylic acid (0.046 g, 0.40 mmol)And N,N-dimethylformamide (10.0 mL),2-(7-Azobenzotriazole)-N,N,N’,N’-tetramethyluronium hexafluorophosphate added at 0 ¡ãC(0.15g, 0.39mmol)N,N-Diisopropylethylamine (0.13 mL, 0.79 mmol) was stirred at room temperature overnight.Quenched with water, extracted with ethyl acetate (30 mL¡Á2).The organic phase was washed sequentially with water (30 mL) and brine (30 mL).Dry over anhydrous sodium sulfate, suction filtration,The residue was purified by silica gel column chromatography (dichloromethane/methanol (v/v) = 80/1, 0.5percent triethylamine).A white solid (0.067 g, 53.0percent) was obtained.

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

Reference£º
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Wang Xiaojun; Zuo Yinglin; Yu Chuan; Yang Chuanwen; Wang Jiancheng; Li Jing; Cao Shengtian; Wu Fangyuan; Zhang Yingjun; S ¡¤geerdeman; (79 pag.)CN108690016; (2018); A;,
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17347-61-4, 2,2-Dimethylsuccinicanhydride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-(4-Bromophenyl)-2, 2-dimethyl-4-oxo-butyric acid 67. To a stirred suspension of 2,2-dimethylsuccinic anhydride (0.641 g, 5.0 mmol) in bromobenzene (3.3 mL), cooled to -10¡ã C (ice/acetone bath) was added aluminium trichloride (1.34 g, 10 mmol) and the reaction was allowed to warm slowly to rt with stirring overnight. The resulting brown solution was poured into cooled (ice bath) aqueous HCl (10 mL, 18percent) and stirred for a further 30 min while the solution was allowed to warm to r.t. No precipitate formed therefore DCM (10 mL) was added and the organic layer was separated and concentrated under reduced pressure to give a solution of the product in PhBr. To this was added hexane followed by a small amount of DCM and the resulting white needles were collected by filtration. Yield 51percent: 1H NMR delta (270 MHz, DMSO-d6) 1.24 (6H, s), 3.29 (2H, s), 7.69 (2H5 d, J= 8.7 Hz), 7.88 (2H, d, J= 8.7 Hz), 7.96 (IH5 s); HPLC > 93percent (R1 2.87, 70percent MeCN in H2O); APCI (M-H)” 283.15, 285.10 m/z.

17347-61-4, As the paragraph descriping shows that 17347-61-4 is playing an increasingly important role.

Reference£º
Patent; STERIX LIMITED; WO2007/96647; (2007); A2;,
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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,42417-39-0

The reactor was charged with HSL ¡¤ HCl, methanol and / or water as described in Table 9 below. The reactor was charged with Pt (5) / Ac and NO / N2 (15 atm, 1: 1 (v / v)). The reaction was carried out at a reaction time and a reaction temperature as shown in Table 9 below. The product was partially recovered and the components were analyzed. The results are shown in Table 9 below.

42417-39-0 3-Aminodihydrofuran-2(3H)-one hydrochloride 445963, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; CJ CHEILJEDANG CORPORATION; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; YANG, YOUNG RYEOL; KIM, BYUNG SIK; KIM, JEONG HYUN; LEE, JUNG HO; SHIN, HYUN KWAN; KIM, JU NAM; CHO, KYUNG HO; (40 pag.)KR2015/118287; (2015); A;,
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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 27 (0338) 5-(1-Naphthylmethoxymethyl)isoxazole-3-carboxylic acid (0.46 g, 1.6 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (0.26 g, 1.9 mmol), triethylamine (0.19 g, 1.9 mmol) and 1-hydroxybenzotriazole (0.02 g, 0.19 mmol) were added to chloroform (amylene addition product) (3 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.37 g, 1.9 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 0.31 g of N-(tetrahydrofuran-3-ylmethyl)-5-(1-naphthylmethoxymethyl)i soxazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (27)) represented by the following formula. 1H-NMR (CDCl3, TMS, delta(ppm)): 1.66-1.69(1H, m), 2.04-2.13(1H, m), 2.53-2.63(1H, m), 3.46(2H, t), 3.58-3.60(1H, m), 3.75-3.79(1H, m), 3.84-3.94(2H, m), 4.68(2H, s), 5.06(2H, s), 6.72(1H, s), 6.95(1H, br s), 7.43-7.58(4H, m), 7.84-7.89(2H, m), 8.11(1H, d), 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.915095-89-5,(S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran,as a common compound, the synthetic route is as follows.

915095-89-5, To the solution of (S)-3-(4-(5-bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran in tetrahydrofuran n-BuLi (2.5 mol) in hexane added at a rate that maintained the reaction temperature below -90C followed by addition of 2,3,4,6-tetra-0-trimethylsilyl-P-D- glucolactone in toluene at a rate that maintained the reaction temperature below -90C. The solution was stirred for 30 min at -95C prior to quenching by addition of methanol containing methanesulfonic acid. The reaction mixture was stirred overnight as the temperature raise to 20C. After completion of reaction, the reaction was quenched by the addition of triethylamine and distilled it out under vacuum. To the obtained residue water was added and extracted thrice with ethylacetate. The combined ethylacetate fractions were washed with brine and dried over sodium sulfate. The reaction mixture was concentrated to provide formula C in the form oil. To the methylenechloride solvent, aluminum chloride was added in one lot and cooled the mass to the temperature 0C to 10C. To the prepared solution acetonitrile was added followed by addition of triethyl silane at a rate such that the temperature was maintained between 0C to 10C. Mixed the above prepared complex with oil of formula C and stirred for 2 h. When HPLC analysis revealed that the reaction was completed, the reaction was quenched by addition of 50% aqueous hydrochloric acid solution. Aqueous layer was extracted with methylenechloride. Combined organic layer washed with 5% aqueous hydrochloric acid solution followed by water and brine. The organic layer was distilled and the obtained residue was added methylenechloride, acetic anhydride and dimethylaminopyridine, pyridine and stirred for 5-6 h. Water was added to the reaction mixture and layers were separated. The methylenechloride layer was distilled and ethanol was added to it followed by heating to 55-60C. The reaction mixture was cooled, filtered and dried to obtain acetylated empagliflozin of formula F.Yield: ~ 58%. Purity (by HPLC): >99.8%

The synthetic route of 915095-89-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PIRAMAL ENTERPRISES LIMITED; GHARPURE, Milind; SHARMA, Sanjay Kumar; VISHWASRAO, Sandesh; VICHARE, Prasad; VARAL, Dipak; (24 pag.)WO2018/207111; (2018); A1;,
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