Heterocyclic Building Blocks-Tetrahydrofuran

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.111769-27-8,(R)-Tetrahydrofuran-3-amine 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

Example 15 (R)-1-Methyl-N-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N4-(tetrahydrofuran-3-yl)-1H-pyrazole-4,5-dicarboxamide A mixture of 1-methyl-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1H-pyrazole-4-carboxylic acid (100 mg, 276 mumol), (R)-tetrahydrofuran-3-ylamine4-methylbenzenesulfonate (143 mg, 552 mumol), diisopropylethylamine (193 mul, 1.1 mmol) and propylphosphonic anhydride (50% in ethyl acetate, 407 mul, 690 mumol) in tetrahydrofurane (7 ml) is refluxed for 18 hours. The solvent is evaporated and to the residue is added sat. aqueous sodium hydrogencarbonate solution. The mixture is stirred for 20 minutes while a white solid precipitates. The solid is collected by filtration, washed with diethylether and dried affording (R)-1-methyl-N-5-(2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N4-(tetrahydrofuran-3-yl)-1H-pyrazole-4,5-dicarboxamide (114 mg, 95.7%) as a white solid. mp.: >250 C. MS: m/z=432.3 (M+H+)., 111769-27-8

As the paragraph descriping shows that 111769-27-8 is playing an increasingly important role.

Reference£º
Patent; Flohr, Alexander; Gobbi, Luca; Groebke Zbinden, Katrin; Koerner, Matthias; Peters, Jens-Uwe; US2012/142665; (2012); 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.

Production Example 264 (0585) 5-(4-Methyl-2,3,5,6-tetrafluorobenzyloxymethyl)isoxaz ole-3-carboxylic acid (0.29 g, 0.9 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (0.21 g, 1.5 mmol), triethylamine (0.15 g, 1.5 mmol) and 1-hydroxybenzotriazole (0.01 g, 0.1 mmol) were added to chloroform (amylene addition product) (2.5 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.23 g, 1.2 mmol) was added to the mixture at room temperature, and the mixture was stirred at room temperature 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 0.06 g of N-(tetrahydrofuran-3-ylmethyl)-5-(4-methyl-2,3,5,6-tetraflu orobenzyloxymethyl)isoxazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (273)) represented by the following formula. 1H-NMR (CDCl3, TMS, delta (ppm)) : 1.63-1.74 (1H, m), 2.04-2.15 (1H, m), 2.29(3H, s), 2.53-2.65 (1H, m), 3.47(2H, t), 3.61 (1H, dd), 3.74-3.82(1H, m), 3.84-3.97(2H, m), 4.68(2H, s), 4.71 (2H, s), 6.76 (1H, s), 7.01 (1H, br 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;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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

A solution of ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate (897 mg, 3.86 mmol) (Aldrich) and triethylamine (1.2 ML, 870 mg, 8.49 mmol) (Aldrich) in dioxane (20 ML) was treated with (R)-3-aminotetrahydrofuran p-toluene-sulfonic acid salt (1.0 g, 3.86 mmol) (Fluka).The mixture was stirred at reflux for 1 hour, then cooled and partitioned between brine and ethyl acetate.The organic layer was dried over sodium sulfate, filtered, concentrated and the residue was purified by chromatography with a silica gel column using a 0-100% ethyl acetate in hexanes gradient to give (R)-2-methylsulfanyl-4-(tetrahydrofuran-3-ylamino)-pyrimidine-5-carboxylic acid ethyl ester as a colorless viscous oil. (Yield 1.0 g, 92%). HRMS m/z calcd for C12H17N3O3S [M+]: 283.0991. Found: 283.0989.

111769-27-8, The synthetic route of 111769-27-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Chen, Yi; Dermatakis, Apostolos; Liu, Jin-Jun; Luk, Kin-Chun; Michoud, Christophe; Rossman, Pamela Loreen; US2004/204427; (2004); 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.17347-61-4,2,2-Dimethylsuccinicanhydride,as a common compound, the synthetic route is as follows.

2,2-Dimethylsuccinic anhydride (2 g, 8×2 mmol) was added to a stirred mixture of dihydrobetulinic aldehyde (1 g, 2 mmol) and A- dimethylaminopyridine (2.2 g, 8×2 mmol) in anhydrous pyridine 15 mL at room EPO temperature. The reaction mixture was stirred for 48 hours at 60 C and cooled down to room temperature. The mixture was diluted with 5percent HCl solution (50 mL), the off-white precipitate was filtered off, washed with water (2x 20 mL) and dried. Washing with hot methanol gave white solids (0.83 g, 67percent total yield).1H NMR (CDCl3): delta 9.63 (s, IH), 4.5 (dd, J1 = 10.1 Hz, J2 = 5.5 Hz, IH), 2.6 (m, 2H), 2.25-0.6 (m, 53H)., 17347-61-4

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

Reference£º
Patent; REGENTS OF THE UNIVERSITY OF MINNESOTA; WO2006/105356; (2006); A2;,
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

To a solution of tetrahydro-3-furanmethanol (6.2 g, 60.8 mmol) in 60 mL tetrahydrofuran was added p-toluenesulfonyl chloride (11.6 g, 60.9 mmol) in one portion, followed by the drop-wise addition of triethylamine (9.2 mL, 66.4 mol) over 10 min. The resulting mixture was stirred at reflux for 16 h and then treated with triethylamine (1.6 mL, 11.5 mmol). Heating was continued for an additional 18 h. The cooled mixture was diluted with diethyl ether, washed with water and brine, and dried over MgSO4. The mixture was then filtered and concentrated under reduced pressure. The resulting residue was placed on a column of silica gel (30 g) and eluted with 5% to 80% ethyl acetate in hexanes to give 11.0 g (72%) of the title compound as an orange oil.1H NMR (CDCl3) delta 7.79 (m, 2H), 7.36 (m, 2H), 3.88-4.04 (m, 2H), 3.64-3.84 (m, 3H), 3.50 (dd, IH), 2.53-2.67 (m, IH), 2.46 (s, 3H), 1.96-2.05 (m, IH), 1.50-1.64 (m, IH)., 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; E. I. DU PONT DE NEMOURS AND COMPANY; WO2009/61761; (2009); A2;,
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, j00431j To a solution of (R)-1-(tetrahydrofuran-2- yl)-methanol (0.50 g, 4.9 mmol), and DIPEA (2.56 mL, 14.7 mmol) in methylene chloride (20 mL) at 0 C was added methanesulfonyl chloride (398 jiL, 5.14 mmol). After 1 h at 0 C, the reaction was stirred at room temp over night (16 h) then quenched with H20 (20 mL), extracted with DCM (3 x 30 mL). The combined organic layers were washed with H20, dried (Na2504) and concentrated to give 551 mg (62%) of crude product. This material was used for next step without purification.

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

Reference£º
Patent; CEPHALON, INC.; BECKNELL, Nadine, C.; DANDU, Reddeppa, Reddy; DORSEY, Bruce, D.; GOTCHEV, Dimitar, B.; HUDKINS, Robert, L.; WEINBERG, Linda; ZIFICSAK, Craig, A.; ZULLI, Allison, L.; (411 pag.)WO2016/205633; (2016); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

453-20-3, 3-Hydroxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 1 L flask, 3-tetrahydrofuran (3-OH-THF, 60.6 g, 0.68 mol, 1 equ.) was charged, followed by DCM (620 mL) and TEMPO(1.08 g, 0.0069 mol, 0.01 equ.) The solution was cooled to -5 ¡ãC. To which TCCA (159.6 g, 0.68 mol, 1 equ.) was added in portions controlling the tern- perature around -5 ¡ãC to 0 ¡ãC. The resulting mixture was allowed to warm to rt and monitored by GC-MS, Reaction was finished in 1 h to give 95percent yield (GC areapercent)., 453-20-3

The synthetic route of 453-20-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Boehringer Ingelheim International GmbH; XING, Lidong; DONG, Weitong; LU, Jun; SCHOLZ, Ulrich; YAN, Jun; YANG, Jinsong; US2014/275579; (2014); A1;,
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

0.190 mmol of 3-methyldihydrofuran-2,5-dione is added to a solution of 0.173 mmol of 2′-benzyl-2′-azabicyclo[2.2.1]hept-7′-ylmethyl 2-amino-5-bromobenzoate, obtained in accordance with Example 3, in 1 ml of acetic acid, and the mixture is heated at 80¡ã C. for 12 hours. The mixture is subjected to conventional work-up, giving 2-benzyl-2-azabicyclo[2.2.1]hept-7-ylmethyl 5-bromo-2-(3′-methyl-2′,5′-dioxopyrrolidin-1′-yl)benzoate; ESI 512; salt precipitation using 0.5M HCl solution gives 2-benzyl-2-azabicyclo[2.2.1]hept-7-ylmethyl 5-bromo-2-(3′-methyl-2′,5′-dioxopyrrolidin-1′-yl)benzoate hydrochloride., 4100-80-5

The synthetic route of 4100-80-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Schiemann, Kai; Leibrock, Joachim; US2004/110788; (2004); 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.13031-04-4,4,4-Dimethyldihydrofuran-2,3-dione,as a common compound, the synthetic route is as follows.,13031-04-4

A rhodium catalyst precursor [Rh(COD)Cl]2, a chiral bisphosphine ligand 3 (R1 = Boc), a polyether alkylguanidinium salt ionic liquid [ (PG), CH3 (EO) 16TMG] SO3CH3, ketopantolactone and benzene, the molar ratio of 3 to Rh is 1.1: 1, the mass ratio of ionic liquid to rhodium catalyst precursor is 500: 1, the ratio of ketopantolactone to Rh The molar ratio is 100: 1, the volume ratio of benzene to ionic liquid is 4: 1, the atmosphere is replaced with nitrogen or argon for 4-6 times, and then pressurized with hydrogen to 5.0MPa, the reaction is carried out at 50 for 4 hours and then rapidly cooled After hydrogen was vented, the benzene was removed under reduced pressure and extracted twice with methyl tert-butyl ether. The volume ratio of methyl tert-butyl ether to benzene was 1: 1. The system was split into two phases and was isolated by simple phase separation The upper methyl tert-butyl ether phase containing D-pantolactone was analyzed by gas chromatography. The conversion of ketopantolactone was 77.6%, and the ee value of D-pantolactone was 60.7%. The reaction conditions and procedures were the same as in Example 1 except that the solvent was changed to toluene, the molar ratio of ketopantolactone to Rh was 200: 1, the pressure of hydrogen was 0.1 MPa, the reaction temperature was 25 C, and the reaction time was 2h. Analysis by gas chromatography showed that the conversion rate of ketopantolactone was 97.5% and that of D-pantolactone was 92.2%.

The synthetic route of 13031-04-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Qingdao University of Science and Technology; Jin Xin; Li Shumei; Cui Feifei; (8 pag.)CN104761518; (2017); B;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

52079-23-9, (S)-(-)-alpha-Hydroxy-gamma-butyrolactone is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Methanesulfonic acid 2-oxo-tetrahydro-furan-3S-yl ester Methanesulfonyl chloride (1.67 ml, 21.56 mmol) was added to a stirred solution of (S)-3-hydroxy-2-oxo-tetrahydrofuran (2 g, 19.6 mmol), 4-N,N-dimethylaminopyridine (240 mg, 1.96 mmol) and diisopropylethylamine (3.76 ml, 21.56 mmol) in dry dichloromethane (20 ml), under nitrogen, at -40 C. The mixture was stirred for 30 minutes and then allowed to warm up to room temperature, then it was washed with 2M hydrochloric acid solution (50 ml), dried and evaporated to a solid. The crude product was purified by flash chromatography on silica gel, eluding with ethyl acetate-cyclohexane (1:1). Trituration with diethylether and drying in vacuo afforded the title compound as a crystalline white solid (2.23 g, 63%): mp. 70-75 C.; NMR delta (CDCl3) 5.33 (1H, t, J 8 Hz), 4.53 (1H, dt, J 9 and 2 Hz), 4.34 (1H, dt, J 10 and 6 Hz), 3.28 (3H, s), 2.86-2.72 (1H, m), 2.65-2.47 (1H, m)., 52079-23-9

The synthetic route of 52079-23-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Glaxo Wellcome Inc.; US6197761; (2001); B1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem