Heterocyclic Building Blocks-Tetrahydrofuran

149809-43-8, ((3R,5R)-5-((1H-1,2,4-Triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl 4-methylbenzenesulfonate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Add to 50ml single-mouth reaction bottle1-((2R,3S)-2-(Benzyloxy)-pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)- 1H-1,2,4-triazole-5(4H)-one (1 g, 1.947 mmol, 1 eq.),((3S,5R)-5-((1H-1,2,4-Triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl P-toluenesulfonate (1.03g,2.181mmol, 1.12eq.),DMSO (6 ml) was dissolved by stirring, and 50 wt% NaOH (202.5 mg, 2.531 mmol, 1.3 eq.) was added and stirred at 45 C.TLC showed complete reaction after 2 h.The reaction was dropped into water, stirred, suction filtered, and the filter cake was washed with water (50ml). Isopropanol crystallized to give 1.52g of a white solid, yield 98.7%

As the paragraph descriping shows that 149809-43-8 is playing an increasingly important role.

Reference£º
Patent; Yangzijiang Pharmaceutical Group Co., Ltd.; Shanghai Pharmaceutical Industry Institute; Huang Huoming; Lv Huimin; Xiao Zhichao; Cai Wei; Ren Zhongjie; Zhou Ting; Liu Zhenren; Zhou Weicheng; Zhang Haibo; (35 pag.)CN108341754; (2018); A;,
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Tetrahydrofuran | (CH2)3CH2O – PubChem

57595-23-0, Methyl 4-oxotetrahydrofuran-3-carboxylate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a stirred solution of 35b (3.0 g, 13.8 mmol) in AcOH (20 mL) was added ethyl 2-oxocyclopentanecarboxylate (2.37 g, 15.2 mmol) at room temperature and the reaction mixture was allowed to be heated at reflux and stirred for 3 h. The reaction mixture was cooled to room temperature and diluted with Et2O/hexane (1:3). The precipitates were collected by filtration to give 3-(2-methyl-4-methoxyphenyl)-2-methyl-6,7-dihydro-5H-cyclopenta[d]pyrazolo[1,5-a]pyrimidin-8-ol (3.88 g, 91% yield) as an off-white powder, which was used for the next reaction without further purification.

The synthetic route of 57595-23-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Saito, Tetsuji; Obitsu, Tetsuo; Kondo, Takashi; Matsui, Toshiaki; Nagao, Yuuki; Kusumi, Kensuke; Matsumura, Naoya; Ueno, Sonoko; Kishi, Akihiro; Katsumata, Seishi; Kagamiishi, Yoshifumi; Nakai, Hisao; Toda, Masaaki; Bioorganic and Medicinal Chemistry; vol. 19; 18; (2011); p. 5432 – 5445;,
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Tetrahydrofuran | (CH2)3CH2O – PubChem

57595-23-0, Methyl 4-oxotetrahydrofuran-3-carboxylate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 1 5,7-dihydrofuro[3,4-d]pyrimidine-2,4(1H,3H)-dione: To Methyl 4-oxotetrahydrofuran-3-carboxylate (18.30 g), urea (11.44 g), methanol (100 mL) and concentrated hydrochloric acid (5 mL) were added. The mixture was refluxed with heating for two hours. The obtained suspension was stirred for 15 minutes in an ice-bath. The precipitate was filtered under reduced pressure, and washed with water (20 mL x 2 times). 2 mol/L aqueous solution of sodium hydroxide (100 mL) and water (30 mL) were added to the obtained precipitate. The mixture was refluxed with heating for 1 hour. Concentrated hydrochloric acid was dropped to the reaction solution in an ice-bath. The precipitate was filtered under reduced pressure, and then the precipitate was washed with water and acetone, dried under reduced pressure to give the title compound (15.7 g) having the following physical data. TLC: Rf 0.32 (methanol: ethyl acetate = 10 : 1); 1H-NMR (300MHz, DMSO-d6). delta 11.23, 11.44-11.10, 11.00, 4.70.

As the paragraph descriping shows that 57595-23-0 is playing an increasingly important role.

Reference£º
Patent; ONO PHARMACEUTICAL CO., LTD.; EP1666468; (2006); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4344-84-7,5-Oxotetrahydrofuran-2-carboxylic acid,as a common compound, the synthetic route is as follows.

(2) room temperature and nitrogen protection,Compound 2 was dissolved in 700 mL of THF,Cooling to 0 ,Began to slowly add 345mL B2H6.Me2S, with bubbles,1h after the drop is completed, the system was green turbidity,Natural recovery to room temperature reaction 1h,System cooling to 0 ,To the system slowly add 500mL methanol quenching,Then returned to room temperature,45 water pump and pump concentrated dry.Vacuum distillation, external temperature 150 ,The temperature of 60 began to produce products.Outside the temperature of 160 , the temperature of 110 -120 stable product to the end,Distilled to give 16 g of product (Compound 3).

4344-84-7 5-Oxotetrahydrofuran-2-carboxylic acid 636468, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; Si Fenke Si Pharmaceutical Research And Development (Tianjin) Co., Ltd.; Yao Qingjia; Wu Simin; Xu Yangjun; (6 pag.)CN106748972; (2017); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19311-37-6,3-Bromotetrahydrofuran,as a common compound, the synthetic route is as follows.

10560] To 2.lh (18 mg, 0.047 mmol) was added DMF (Volume: 0.5 mE) and cesium carbonate (53.8 mg, 0.165 mmol). The reaction was stirred at room temperature for 5 minutes then 3-bromotetrahydrofuran (17.81 mg, 0.118 mmol) was added. The reaction was heated to 70 C. and stirred for 3 hours or until done by ECMS. The reaction was cooled, 0.5 ml of DMF was added, then filtered through a 0.45 nM in line filtet The DMF solution with the desired product 2.37a was used as is for the next step, assume quantitative yield. EC-MS (mlz): 452.4 [M+H], 0.75 mm.

As the paragraph descriping shows that 19311-37-6 is playing an increasingly important role.

Reference£º
Patent; Novartis AG; FU, Jiping; HAN, Wooseok; KARUR, Subramanian; LU, Peichao; PFISTER, Keith Bruce; YOUNG, Joseph Michael; (97 pag.)US2018/312507; (2018); A1;,
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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-naphthylmethyl) thiomethyl] isoxazole-3-carboxylic acid chloride ( In ethyl acetate solution (30 mL) Tetrahydrofuran-3-ylmethylamine hydrochloride (1.00 g, 7.26 mmol) And 1 mol / L sodium hydroxide aqueous solution (16 mL) Were simultaneously added at room temperature. After vigorously stirring at room temperature for 1 hour, 1 mol / L sodium hydroxide aqueous solution was added. The separated organic layer was washed successively with water and saturated brine, After drying over anhydrous magnesium 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 – [(2-naphthylmethyl) thiomethyl] isoxazole-3-carboxamide (Hereinafter referred to as present amide compound (253)) 480 mg was obtained.

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;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5061-21-2,2-Bromo-4-butanolide,as a common compound, the synthetic route is as follows.

General procedure: Anhydrous K2CO3 (5 equiv) was added to the solution of relevantamine (1 equiv) and tetrabutylammonium bromide (TBAB)(0.01 equiv) in the acetonitrile and the mixture was stirred at at0 C for 1.5 h. Then a solution of 3-bromodihydrofuran-2(3H)-one(8) or 3-bromo-5-methyldihydrofuran-2(3H)-one (9) (1 equiv)was added dropwise and stirring was continued for 12-48 h atroom temperature. After the reaction was completed, the precipitatewas filtered off and the filtrate was concentrated under vacuum.Obtained crude products were purified by columnchromatography. Reagents and conditions: 6.03mmol 4 (1.43g), 30.19mmol K2CO3 (4.17g), 0.06mmol TBAB (0.02g), 6.03mmol 8 (1.00g), 15ml MeCN, 48h; purification by column chromatography (S6); Yield 78%; yellow oil; Rf: 0.70 (S6); 1H NMR (CDCl3) delta [ppm]: 2.17-2.20ppm (m, 2H(CH2CH2N)), 2.23-2.30 (m, 2H(NCHCH2)) 2.31 (s, 3H (Me)), 2.68-2.74ppm (t, 2H (CH2N)), 3.62-3.68ppm (t, 1H(NCH)), 4.13-4.37ppm (m, 2H(CH2CH2O), 6.13 (t, 1H(C=CH)), 7.17-7.40ppm (m, 10H (Ar)), ESI-MS (m/z) 322.1 [M+H]+

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

Reference£º
Article; Kowalczyk, Paula; Sa?at, Kinga; Hoefner, Georg C.; Guzior, Natalia; Filipek, Barbara; Wanner, Klaus T.; Kulig, Katarzyna; Bioorganic and Medicinal Chemistry; vol. 21; 17; (2013); p. 5154 – 5167;,
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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

Step 4. A solution of furo[2,3-c]pyridine-2-carboxylic acid (60 mg, 0.37 mmol, 1 .16 equiv) EDCI (70 mg, 0.37 mmol, 1 .1 5 equiv), HOBt (45 mg, 0.33 mmol, 1 .05 equiv), and triethylamine (0.5 mL) in DMF (4 mL) was stirred for 10 min at rt. (5-[[3-(Trifluoromethyl)benzene] sulfonyl] pyridin-2-yl)methanamine ( 100 mg, 0.32 mmol, 1 00 equiv) was then added and the reaction mixture was stirred overnight at rt. The resulting solution was diluted with 120 mL of ethyl acetate and washed with 2×100 mL of water. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column with ethyl acetate/petroleum ether ( 1 : 1 – 1 :9) to give 46.4 mg (32%) of the title compound as a light yellow solid. 1HNMR (300 MHz, DMSO-d6) delta 9.59 (t, J= 6.0 Hz, 1H), 9.15 (d, J= 1.8 Hz, 1H), 9.03 (s, 1H), 8.38 (m, 2H), 8.31 (m, 2H), 8.07 (d, J = 8.1 Hz, 1H), 7.79 (m, 2H), 7.57 (m, 2H), 4.62 (d, J= 6.0 Hz, 2H). LC/MS (Method F, ESI): RT= 1.44 min, m/z – 462.0 [M+H]+.

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

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;,
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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.

In the same apparatus as in Example 1, The residue (Ir-Pt -Re catalyst (1)) obtained in Example 1, and 0.342 g (3.0 mmol) of epsilon-caprolactone were added, It was made up with 1,2-dimethoxyethane to make epsilon-caprolactone 5%. Pressurized to 8.0 MPa with hydrogen gas, the mixture was reacted at 80 C. for 2 hours with stirring. After completion of the reaction, the resulting reaction solution was cooled to room temperature, And then filtered through a syringe equipped with a membrane filter (0.45 mum). When the obtained filtrate was analyzed by gas chromatography, The conversion of epsilon-caprolactone is 100% The yield of 1,6-hexanediol was 92.3%. The selectivity was 92.3% The yield of 1-hexanol was 8.0% The selectivity was 8.0%. In Example 1A, The catalyst was added to the Ir-Pt-Re catalyst (2) prepared in Example 2, A 1,2-dimethoxyethane solution of 5% epsilon-caprolactone was added to 50% gamma-valerolactone 1, To a 2-dimethoxyethane solution (7.5 mmol of gamma-valerolactone) Except for changing the reaction time to 4 hours, The reaction was carried out in the same manner as in Example 1A. When the obtained filtrate was analyzed by gas chromatography, The conversion of gamma-valerolactone was 50.0% . The yield of 1,4-pentanediol was 40.0%. The selectivity was 80.0%. The yield of 2-pentanol was 10.1% . The same selectivity was 20.2%.

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Reference£º
Patent; UBE INDUSTRIES LIMITED; YOSHII, KIYOTAKA; YAMADA, ATSUSHI; (22 pag.)JP2015/86199; (2015); A;,
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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.

A 0 C. suspension of (R)-(+)-tetrahydro-3-furylamine p-toluenesulfonate salt (1.00 g, 3.86 mmol) in THF (40 mL) was treated with NaH (60% in mineral oil, 0.170 g, 4.24 mmol), stirred at 0 C. for 1.5 h, treated with 2-chloroethyl isocyanate (0.362 mL, 4.24 mmol) and stirred at RT overnight as the cooling bath expired. The mixture was treated with satd. NH4Cl and water, extracted with EtOAc (2*) and the combined organics were washed with brine (2*), dried over Na2SO4 and concentrated to dryness. The residue was treated with 1:1 EtOAc/Hex and the resulting solid collected via filtration to afford (R)-1-(2-chloroethyl)-3-(tetrahydrofuran-3-yl)urea (522 mg, 70%). MS (ESI) m/z: 193.1 (M+H+).

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

Reference£º
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Samarakoon, Thiwanka; Caldwell, Timothy Malcolm; Vogeti, Lakshminarayana; Ahn, YuMi; Patt, William C.; Yates, Karen M.; US2014/315917; (2014); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem