Heterocyclic Building Blocks-Tetrahydrofuran

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.

General procedure: 3-aminobenzamide (50 mg, 0.37 mmol) and maleic anhydride (43.2 mg, 0.44 mmol) were dissolved in dry THF (1 ml) and stirred at room temperature for 18 hours. The precipitate was filtered off and dried in vacuo to give 2 (71 mg, 83%).

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

Reference£º
Article; Ekblad, Torun; Lindgren, Anders E.G.; Andersson, C. David; Caraballo, Remi; Thorsell, Ann-Gerd; Karlberg, Tobias; Spjut, Sara; Linusson, Anna; Schueler, Herwig; Elofsson, Mikael; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 546 – 551;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.63095-51-2,(R)-4-Propyldihydrofuran-2(3H)-one,as a common compound, the synthetic route is as follows.

63095-51-2, To a 250 ml three-necked flask with mechanical stirring function was added compound I (12.8 g, 99.9 mmol), L-2-aminobutyramide (20.4 g, 20.0 mmol), and ethanol (50 ml). Stir at reflux for 24h. The reaction solution was concentrated, purification by column chromatography gave the compound.

As the paragraph descriping shows that 63095-51-2 is playing an increasingly important role.

Reference£º
Patent; Fujian Haixi New Drug Initiative Co., Ltd.; Kang Xinshan; Wang Ruyong; Ye Yizhang; Gong Xuan; Zhang Fengsen; Wang Zhonghong; Li Dandan; Fu Yueli; Feng Yan; (35 pag.)CN110357790; (2019); A;,
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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.

5-Butyl-1,2,4-oxadiazole-3-carboxylic acid (1.36 g, 8 mmol), Tetrahydrofuran-3-ylmethylamine hydrochloride (1.65 g, 12 mmol), Triethylamine (1.21 g, 12 mmol) And 1-hydroxybenzotriazole (0.11 g, 0.8 mmol) Was added to chloroform (amylene added product) (16 mL). To the mixture, 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (1.83 g, 12 mmol) was added at room temperature, After stirring overnight, Add water, It was extracted three times with chloroform. The organic layer was washed with saturated brine, After drying with anhydrous sodium 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-butyl-1,2,4-oxadiazole-3-carboxamide (Hereinafter referred to as the amide compound (57)) 0.76 g was obtained.

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; SUMITA, YUSUKE; (264 pag.)JP2015/51963; (2015); A;,
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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

Production Example 142 (0462) 5-(2-Phenoxyethoxymethyl)isoxazole-3-carboxylic acid (1.40 g, 5.3 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (0.88 g, 6.4 mmol), triethylamine (0.65 g, 6.4 mmol) and 1-hydroxybenzotriazole (0.08 g, 0.64 mmol) were added to chloroform (amylene addition product) (20 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (1.23 g, 6.4 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 1.60 g of N-(tetrahydrofuran-3-ylmethyl)-5-(2-phenoxyethoxymethyl)iso xazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (149)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)):1.66-1.69(1H, m), 2.05-2.13(1H, m), 2.56-2.60(1H, m), 3.47(2H, t), 3.56-3.61(1H, m), 3.74-3.80(1H, m), 3.84-3.88(1H, m), 3.91-3.93(3H, m), 4.15-4.17(2H, m), 4.77(2H, s), 6.76(1H, s), 6.90-7.00(4H, m), 7.27-7.32(2H, m), 184950-35-4

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; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (2015); A1;,
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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

Stage II: Preparation of N-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl) methylamino]propyl]tetrahydrofuran-2-carboxamide (Alfuzosin); Ethyl chloroformate (22.35 g, 0.206 mol) was added to a mixture of tetrahydrofuran-2- carboxylic acid (23.90 g, 0.206 mol), and triethylamine (20.80 g, 0.206 mol) in methylene dichloride (300 ml) at 0-50C. The stirring was continued for 30 min at 0-50C to complete the formation of mixed anhydride. To this, mixture of N]-(4-amino-6,7- dimethoxyquinazolin-2-yl)-Ni-methylpropane-l,3-diamine (50 g, 0.172 mol) in methylene dichloride (200 ml) was added at 0-50C and stirring was continued for additional 1 hr at 0-50C to complete the reaction. Thereafter, water was added to the reaction mass and pH was adjusted to 4.0-4.5. The organic layer was discarded and the pH of the aqueous layer was raised to 10-10.5 with aqueous sodium hydroxide. The aqueous layer was extracted with methylene dichloride and the organic extract was concentrated to remove methylene dichloride. The concentrated mass was stirred with acetone to afford Alfuzosin. The product was filtered and dried under vacuum. Yield: 50 g (75percent of theory). HPLC purity: 99.97percent.

16874-33-2, As the paragraph descriping shows that 16874-33-2 is playing an increasingly important role.

Reference£º
Patent; AUROBINDO PHARMA LIMITED; WO2007/74364; (2007); A1;,
Tetrahydrofuran – Wikipedia
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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.

Tetrahydrofuran-3-ylmethylamine hydrochloride (0.55 g, 3.97 mmol) And triethylamine (0.40 g, 3.97 mmol) Was added to chloroform (amylene added product) (15 mL). To the mixture, At room temperature 5- (5,6,7,8-tetrahydronaphthalen-2-ylmethyl) oxymethyl isoxazole-3-carboxylic acid (0.76 g, 2.65 mmol) 1-Hydroxybenzotriazole (0.04 g, 0.26 mmol) And 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0. 76 g, 3.97 mmol) After stirring at room temperature for 5 hours, Dilute hydrochloric acid was added, It was extracted twice with chloroform. The organic layer was washed with saturated sodium bicarbonate water, After drying with anhydrous sodium sulfate, And concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, The following equationIndicated by N- (tetrahydrofuran-3-ylmethyl) -5- (5,6,7,8-tetrahydronaphthalen-2-ylmethyl) oxymethyl isoxazole-3-carboxyamide (Hereinafter referred to as present amide compound (119)) 0.80 g was obtained., 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; SUMITA, YUSUKE; (264 pag.)JP2015/51963; (2015); A;,
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.219823-47-9,(R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

At room temperature, 3-methoxy-4-bromophenol (0.4 g, 1.97 mmol) and cesium carbonate (0.96 g, 2.96 mmol) were added to a solution of compound 15-c (0.43 g, 1.78 mmol) in N,N-dimethylformamide (4 mL) respectively. After the addition, the reaction solution was stirred at 80 C. for 16 hours. The reaction solution was diluted with ethyl acetate (10 mL), washed sequentially with water (10 mL¡Á3) and brine (10 mL¡Á3). The organic phase was dried over anhydrous sodium sulfate and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate=10:1) to give compound 15-b (0.31 mg, yield 64%). (0265) 1H-NMR (400 MHz, CDCl3) delta: 7.40 (d, J=8.4 Hz, 1H), 6.48 (d, J=2.8 Hz, 1H), 6.33 (dd, J=2.8, 8.8 Hz, 1H), 4.85-4.94 (m, 1H), 3.94-4.05 (m, 3H), 3.87-3.94 (m, 1H), 3.86 (s, 3H), 2.07-2.29 (m, 2H) ppm

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; GUANGZHOU MAXINOVEL PHARMACEUTICALS CO., LTD.; XU, Zusheng; ZHANG, Nong; WANG, Tinghan; SUN, Qingrui; WANG, Yuguang; (90 pag.)US2018/208604; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.105-21-5,Gamma-heptalactone,as a common compound, the synthetic route is as follows.

gamma-heptalactone was added into an decarboxylation and dimerisation reactor R1, in which the upper layer of the catalyst bed layers was loaded with Amberlyst catalyst (Amberlyst 15WET), and the lower layer of the catalyst bed layers was loaded with the decarboxylation and dimerisation catalyst B produced above, two catalyst layers having a same packing height. Decarboxylation and dimerisation was conducted under conditions of a temperature of 180 degree Celsius and a WHSV of 1.5 h-1, resulting in a conversion of 96%, and a selectivity to C8 olefin of 81%. After separation, the C8 olefin was fed into an aromatization reactor R2 for aromatization under the actions of a temperature of 500 degree Celsius, an aromatization catalyst MCM-22, and a space velocity of 2 h-1, to provide a stream containing a xylene product, with a selectivity to xylene of 94%, and a yield of carbon as xylene of 73.1%. The olefin not reacted completely could be recycled to the dimer reactor for continued reaction. The olefin obtained was further separated to provide light aromatics comprising benzene, toluene and the like, simultaneously providing PX in high-purity. In addition, an additional part was obtained as a heavy component from the column bottom. Hydrogen out of the column top could be used as a raw material for hydrogenating oligomers into gasoline or diesel oil, while the heavy component from the column bottom could be used as a raw material for diesel oil or be combusted to supply heat., 105-21-5

105-21-5 Gamma-heptalactone 7742, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; CHINA PETROLEUM & CHEMICAL CORPORATION; SHANGHAI RESEARCH INSTITUTE OF PETROCHEMICAL TECHNOLOGY, SINOPEC; KONG, Dejin; ZHENG, Junlin; SONG, Qi; QI, Xiaolan; XU, Xuan; JIANG, Xiangdong; YANG, Deqin; (19 pag.)US2018/282256; (2018); A1;,
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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

To a mixture of 0.7 g of tetrahydrofuran-2 – carboxylic acid and 10 ml of THF was added 0.84 g of oxalyl chloride and 0.05 ml of DMF. The mixture was stirred for 2 hours at room temperature, then, THF was distilled off under reduced pressure. To the residue was added 20 ml of THF and 1.02 g of 3-amino-6- (pyridin- 3-yl ) -pyran-2-one , then, 0.91 g of triethylamine was added, and the mixture was stirred for 18 hours at room temperature. Water (10 ml) was added, and about 15 ml of THF was distilled off under reduced pressure, then, the precipitate was filtrated. The filtratedprecipitate was washed with 10 ml of water and 15 ml of hexane, then, drying under reduced pressure wasperformed to obtain 0.88 g of N- [2-oxo-6- (pyridin-3-yl) – 2H-pyran-3-yl ] -tetrahydrofuran-2-carboxamide(hereinafter, referred to as the inventive compound 49) . Inventive compound 491 H-NMR (CDC13) delta: 9.19 (1H, s), 9.03-9.00 (1H, m) , 8.66- 8.63 (1H, m) , 8.42 (1H, d) , 8.10-8.06 (1H, m) , 7.40 (1H, dd) , 6.79 (1H, d) , 4.48 (1H, dd) , 4.14-4.08 (1H, m) , 4.00-3.95 (1H, m) , 2.42-2.32 (1H, m) , 2.19-2.10 (1H, m) , 2.02-1.91 (2H, m) .

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; SUMITOMO CHEMICAL COMPANY, LIMITED; ARIMORI, Sadayuki; SHUTO, Akira; MIZUNO, Hajime; WO2011/49150; (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.219823-47-9,(R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

Tert-butyl(4-(2-chloro-5-iodobenzyl)phenoxy)dimethylsilane (1 .0 Kg), tetrahydrofuran (6.0 L) and (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl) tetrahydro-2H-pyran-2-one (1 .221 Kg) were charged into a 20 L flask under Nitrogen atmosphere. Toluene (6.0 L) was charged into the flask and the resulted mixture was cooled to -80 C. n-Butyl Lithium in hexane (1 .6M, 2.8 Kg) was added slowly over a period of 3 hours at -80 C. The reaction mixture was maintained for 1 hour at -80 C. A solution of methanesulfonic acid (1 .46 Kg of methanesulfonic acid in 9.0 L of methanol) was added to the reaction mass at -70 C. The reaction mass was heated to -10 C and stirred for 30 minutes and heated to 30 C and stirred for 12 hours at 30 C. The reaction mass was cooled to 5 C and sodium bicarbonate solution (2.0 Kg of sodium bicarbonate in 23 L of water) was added slowly. The reaction mass was stirred for 30 minutes at 30 C. The reaction mass was washed with Toluene (6.0 Lx 3) and the reaction mass was concentrated under vacuum until 20 volumes remains in the flask. The reaction mass was extracted with ethylacetate (10.0 Lx5) and the ethylacetate layer was washed with water (3.0 L). The ethylacetate layer was charged into a 100 L reactor and concentrated under vacuum to 3 volumes remained in the reactor. The concentrated ethylacetate layer was stripped off with acetonitrile (3.0 Lx 3) then dichloromethane (7.0 L) and acetonitrile (1 .2 L) were charged into the reactor and the reaction mass was cooled to -30 C. Triethylsilane (0.57 Kg) and Borontrifluoride etherate solution (1 .307 Kg) were charged into the reactor and the reaction mass was stirred for 3 hours at -30 C. Temperature was raised to -5 C and stirred for 6 hours. A solution of sodium carbonate (2.0 Kg of sodium carbonate in 20.0 L of water) was added to the reaction mass over a period of 30 minutes at 5 C. The reaction mass was heated to 30 C and stirred for 30 minutes. The reaction mass was concentrated under vacuum until 25 volumes remained in the reactor. The mass was washed with toluene (4.0 L) and extracted with ethylacetate (8.0 Lx2 and 4.0 Lx4) and the ethylacetate layer washed with water (2.0 Lx2) The organic layer was concentrated under vacuum until 2 volumes remained in the reactor then the crude mass was stripped off with ethylacetate (3.0 l_x2) and with DMF (1 .4 L). Tosyl-THF (0.634 Kg) and DMF (0.20 L) were charged into the reactor and the resulted mass was stirred for 30 minutes at 30 C. Cesium carbonate lot 1 (0.57 Kg) was added to the reaction mass. Reaction mass was heated to 45 C and stirred for 2 hours at 45 C. Cesium carbonate lot 2 (0.57 Kg) was added to the reaction mass and the reaction mass was stirred for 2 hours. Cesium carbonate lot 3 (0.57 Kg) was added to the reaction mass the reaction mass was stirred for 20 hours at 45 C. The reaction mass was cooled to 30 C and water (4.0 L) was added to the mass and stirred for 30 minutes. Layers were separated and the aqueous layer was washed with toluene (4.0 L). The aqueous layer was concentrated at 70 C under vacuum until 1 .0 volume remained in the reactor. The concentrated mass was cooled to 30 C and water (10.0 L) and acetonitrile 1 .0 L) were charged into the reactor at 30 C and the resulted mixture was heated to 45 C and the mixture was stirred for 6 hours at 45 C. The suspension was cooled to 25 C and stirred for 7 hours at 25 C. The precipitation was filtered and the wet solid was washed with water (3.0L) and the solid was suck dried. The wet compound and DMF (1 .0 L) were charged into another reactor and the solution was heated to 45 C. Acetonitrile (1 .0 L) charged followed by water (10.0 L) into the reactor at 45 C and stirred for 6 hours. The suspension was cooled to 25 C and stirred for 6 hours. The precipitation was fileted and the wet cake was washed with water. The wet material was suck dried. The wet material was dried under vacuum at 60 C for 6 hours to yield 0.55 Kg of crystalline empagliflozin. Purity by HPLC 99%., 219823-47-9

219823-47-9 (R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate 13837325, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; DR. REDDY’S LABORATORIES LIMITED; CHAKKA, Ramesh; PATHIVADA, Deepika; PEDDI REDDY, Subba Reddy; IPPALAPALLI, Sandeep; CHINTADA, Krishnarao; KOYA, Ravi Teja; ORUGANTI, Srinivas; BADARLA, Venkata Krishna Rao; DONIPARTHI, Kiran Kumar; SUD, Abhishek; MADAVARAM, Sateesh; LEKKALA, Amarnath Reddy; KUNHIMON, Syam Kumar Unniaran; JAWLEKAR, Suhas; KANDAGATLA, Bhaskar; (72 pag.)WO2017/203457; (2017); A1;,
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