Heterocyclic Building Blocks-Tetrahydrofuran

88675-24-5, Tetrahydrofuran-3-amine is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 4,6-dichloropyrimidine (0.3 g, 2.014 mmol) in DMF (10 mL) at 0 ¡ãC, was added NaH (0.242 g, 6.04 mmol). After stirred for 5 mm, tetrahydrofuran-3-amine (0.175 g, 2.014 mmol) was added and stirred overnight atRT The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with water (50 mL) and extracted with DCM (80 mL). The organic layer was washed with brine (40 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 6-chloro-N- (tetrahydrofuran-3-yl)pyrimidin-4-amine (0.3 g, 0.872 mmol, 43percent yield) as ayellowish semi-solid. LCMS (ESI) m/e 200.4 [(M+H), calcd for C8H11C1N3O,200.11; LC/MS retention time (method B): tR = 0.60 mm., 88675-24-5

Big data shows that 88675-24-5 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (318 pag.)WO2017/59080; (2017); A1;,
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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,4100-80-5

EXAMPLE A284-(4-acetylaminophenyl)-2-methyl-4-oxobutanoic acid22 ml (0.28 mol) of dimethylformamide were added dropwise to 133.34 g (1.0 mol) of finely powdered aluminium chloride within 20 minutes, while cooling externally with ice. After the strongly exothermic reaction died down, 13.517 g (0.1 mol) of acetanilide and 11.413 g (0.1 mol) of methylsuccinic acid anhydride were added all at once and at an initial temperature of 60¡ã C., during which time the mixture heated up to about 80¡ã C. It was kept for another 3 hours at a temperature of 60-70¡ã C., the still hot mixture was stirred into 1 kg of crushed ice, 60 ml, of conc. hydrochloric acid were added and the mixture was left to stand overnight at ambient temperature. The precipitate formed was suction filtered and thoroughly washed with water. It was taken up in 150 ml of methanol, stirred for 30 minutes at 50¡ã C., then for another 30 minutes while cooling externally with ice and the precipitate was suction filtered. After drying in a circulating air dryer at 60¡ã C., 10.4 g (42percent of theoretical) of colourless crystals were obtained, m.p. 229-231¡ã C. and Rf 0.48 (El I).IR (KBr): 1714.6, 1662.5 cm-1 (CO)

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

Reference£º
Patent; Boehringer Ingelheim Pharma GmbH & Co. KG; US7230001; (2007); B1;,
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Tetrahydrofuran | (CH2)3CH2O – PubChem

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.

88675-24-5, General procedure: All reactions were carried out in vials under nitrogen atmosphere. Step 1: A solution of compound 15 (125?mumol, 1.0?equiv) and compound 16 (125?mumol, 1.0?equiv) in MeOH (0.3?M) was treated with NaHCO3 (250?mumol, 2.0?equiv) and stirred for 16?h at 30?¡ãC. The reaction was then treated with NaBH4 (125?mumol, 1.0?equiv) and stirred for 3?h (LCMS check). The reaction mixture was filtered and concentrated. The crude amine was suspended in 1?N NaOH (1?mL) and extracted with dichloromethane (3?¡Á?1?mL). The organics were pooled, dried (Na2SO4) and evacuated to afford 18. Step 2: A solution of 17 (75?mumol, 0.60?equiv) in DMF (0.1?M) was treated with HATU (75?mumol, 0.60?equiv) followed by the crude amine 18 (125?mumol, 1.0?equiv) and iPr2NEt (225?mumol, 1.8?equiv). The reactions were concentrated and purified directly by reversed phase preparative HPLC using a C18 column and eluting with acetonitrile?water (0.225percent formic acid or pH?=?10 NH4OH) gradient. All compounds were deemed greater than 95percent purity by LCMS and HPLC. #10;

The synthetic route of 88675-24-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Londregan, Allyn T.; Piotrowski, David W.; Futatsugi, Kentaro; Warmus, Joseph S.; Boehm, Markus; Carpino, Philip A.; Chin, Janice E.; Janssen, Ann M.; Roush, Nicole S.; Buxton, Joanne; Hinchey, Terri; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1407 – 1411;,
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5061-21-2, 2-Bromo-4-butanolide is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5061-21-2, (Step 1) To a solution of 2-amino-5-nitrophenol (2.00 g, 13 mmol) in DMF (20 mL) were added 3-bromo-dihydrofuran-2-one and potassium carbonate (2.1 g, 15.57 mmol), and the mixture was stirred at 80C for 4 hr under nitrogen atmosphere. The reaction mixture was allowed to be cooled to room temperature, and filtered through Celite, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate, and the solution was washed with water and saturated brine, and dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained yellow solid was washed with pentane to give 2-(2-hydroxyethyl)-7-nitro-4H-benzo[1,4]oxazin-3-one (2.5 g, 80.9%) as a yellow solid. MS (API) :239 (M+H)

5061-21-2 2-Bromo-4-butanolide 95463, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; YAMAMOTO, Satoshi; SHIRAI, Junya; FUKASE, Yoshiyuki; SATO, Ayumu; KOUNO, Mitsunori; TOMATA, Yoshihide; OCHIDA, Atsuko; YONEMORI, Kazuko; ODA, Tsuneo; IMADA, Takashi; YUKAWA, Tomoya; (238 pag.)EP2975031; (2016); A1;,
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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,4100-80-5

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. To 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 (1.87 g, 7.02 in ethanol (100 mL) was added 2N HCl in diethyl ether (3 mL) was added and the reaction was refluxed for 15 h. The reaction was concentrated under reduced pressure to give a mixture of ethyl 3-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-2-methylpropanoate and ethyl 3-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)butanoate (2.15 g, >100percent yield) as a golden semi-solid. LCMS retention time=2.595 min and 95percent purity, LCMS MH+ 295.

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

Reference£º
Patent; HYDRA BIOSCIENCES, INC.; Chenard, Bertrand L.; Gallaschun, Randall J.; Kimball, Spencer David; US2014/275528; (2014); A1;,
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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.

112372-15-3, A solution of 4-(piperidine-1-sulfonyl)-benzylamine (500 mg, 1.93 mmol, 1 .00 equiv, furo[2,3-c]pyridine-2-carboxylic acid (355 mg, 2.13 mmol, 1 .1 1 equiv), DIPEA (762 mg, 5,79 mmol, 3.00 equiv), and benzotriazol-1- yloxytris(dimethylamino)phosphonium hexafluorophosphate (1044 mg, 2.31 mmol, 1 .20 equiv) in DMF (5 mL) was stirred overnight at rt. The reaction was quenched by the addition of 20 mL of water. The precipitated product was collected by filtration and re-crystallized from ethanol to give 304 8 mg (40%) of the title compound as a light brown solid. NMR (300 MHz, DMSO-d6 delta 9.67-9 63 (t, J = 6 Hz, 1 H), 9.06 (s, 1 H), 8.49-8.48 (d, – 3 Hz, 1 H), 7.84-7.83 (t, ./ = 3 Hz, 1 H), 7.71 -7.69 (d, .7 = 4 Hz, 3H), 7.59-7.57 (d, J = 6 Hz, 2H), 4.60 (d, J = 6.3 Hz, 2H), 2.89-2.84 (m, 4H), 1.61 – 1 .50 (m, 4H), 1.36- 1 .34 (m, 2H). LC/MS (Method H, ESI): RT = 1 .20 min, m/z = 400.0 [M + H]

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.; BUCKMELTER, Alexandre J.; CLODFELTER, Karl H.; DRAGOVICH, Peter; GOSSELIN, Francis; GUNZNER-TOSTE, Janet; HAN, Bingsong; LIN, Jian; LIU, Xiongcai; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; ZAK, Mark; ZHANG, Yamin; ZHAO, Guiling; ZHENG, Xiaozhang; YUEN, Po-Wai; WO2013/127266; (2013); A1;,
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219823-47-9, (R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A suspension of 3-hydroxy-N-(l-rnethyl-lH-pyrazol-3-yl)-5-[(phenylmethyl)oxy]benzamide (450 mg, 1.39 mmol), (3i?)-tetrahydrofuran-3-yl 4- methylbenzenesulfonate (507 mg, 2.09 mmol) and potassium carbonate (481 mg, 3.48 mmol) in acetonitrile (5 mL) was stirred in a Smith Creator microwave at 1600C for 3 hours. The solvent was removed in vacuo and ethyl acetate added. The organics were washed with water (40 mL), brine (40 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give a yellow foam which was chromatographed on silica, eluting with a gradient of 0-100% ethyl acetate in zso-hexane, to give the title compound as a white foam (452 mg). 1H NMR delta (CDCl3): 2.09 – 2.14 (IH, m), 2.14 – 2.24 (IH, m), 3.68 (3H, s), 3.86 – 3.91 (IH, m), 3.94 – 3.98 (3H, m), 4.89 (IH, s), 5.03 (2H, s), 6.64 (IH, t), 6.85 (IH, s), 6.96 (IH, d), 7.07 (IH, t), 7.27 (IH, m), 7.33 – 7.41 (5H, m), 9.31 (IH, s); m/z 394 (M+H)+., 219823-47-9

The synthetic route of 219823-47-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/7041; (2007); A1;,
Tetrahydrofuran – Wikipedia
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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

Step 1: 1-(5-Iodo-pyridin-2-yl)-3,3-dimethyl-pyrrolidine-2,5-dione 5-iodopyridin-2-amine (1 g, 4.55 mmol) was dissolved in DMF (5 ml) and 3,3-dimethyldihydrofuran-2,5-dione (1.28 g, 10.0 mmol, 2.2 equiv.) was added at room temperature. The mixture was stirred for 3 hr at 150¡ã C. The reaction mixture was evaporated to dryness and loaded directly to a silica gel column. The crude material was purified by flash chromatography on silica gel (20 gr, ethyl acetate/heptane gradient, 0:100 to 100:0). The desired 1-(5-iodopyridin-2-yl)-3,3-dimethylpyrrolidine-2,5-dione (1.3 g, 3.94 mmol, 86.6percent yield) was obtained as a yellow solid, MS: m/e=331.0 (M+H+)., 17347-61-4

The synthetic route of 17347-61-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Green, Luke; Guba, Wolfgang; Jaeschke, Georg; Jolidon, Synese; Lindemann, Lothar; Ricci, Antonio; Rueher, Daniel; Stadler, Heinz; Vieira, Eric; US2011/251169; (2011); A1;,
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219823-47-9, (R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a round bottom flask, 1.2 g compound of Formula (II), 1.2 g cesium carbonate, 0.81 (R)-tetrahydrofuran-3-yl-4-methylbenzenesulfonate and 18 mL DMF or DMSO were added at 25 C. to 35 C. The reaction mixture was heated to 35 to 40 C. and stirred for 24-36 hrs. The reaction mixture then cooled to 25 C. to 35 C. 40 mL water and 20 ml toluene were added stirred for 15-20 minutes. Layers were separated. The aqueous layer was extracted with dichloromethane, dried over sodium sulfate. The solvent was distilled out under vacuum. 10 mL ethanol was added and stirred for 30 minutes. The reaction mixture was stirred at 0-5 C. for an hour. The product was filtered and washed with pre-cooled ethanol and dried to obtain empagliflozin., 219823-47-9

The synthetic route of 219823-47-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CADILA HEALTHCARE LIMITED; DESAI, Sanjay Jagdish; PARIHAR, Jayprakash Ajitsingh; RUPAPARA, Mahesh Laljibhai; GANGWAR, Pranav Jitendra; GHODASARA, Hardik Bhikhubhai; (30 pag.)US2017/247356; (2017); A1;,
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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 236 (0557) Tetrahydrofuran-3-ylmethylamine hydrochloride (1.32 g, 9.6 mmol) and triethylamine (1.34 mL, 9.6 mmol) were added to chloroform (amylene addition product) (20 mL), and the mixture was stirred at room temperature for 30 minutes. 5-[3-(2-Fluorophenyl)propyl]isoxazole-3-carboxylic acid (2.0 g, 8.0 mmol), 1-hydroxybenzotriazole (0.1 g, 0.8 mmol) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (1.8 g, 9.6 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 and saturated saline water, and concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 1.94 g of N-(tetrahydrofuran-3-ylmethyl)-5-[3-(2-fluorophenyl)propyl] isoxazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (245)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)):1.63-1.72(1H, m), 2.01-2.12(3H, m), 2.52-2.63(1H, m), 2.71-2.75(2H, m), 2.80-2.84(2H, m), 3.44-3.47(2H, m), 3.57-3.60(1H, m), 3.73-3.79(1H, m), 3.84-3.94(2H, m), 6.47(1H, s), 6.98(1H, brs), 7.00-7.09(2H, m), 7.16-7.22(2H, m), 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
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