Day: November 19, 2020

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.

Under nitrogen atmosphere, to a mixture of 1.4 g of (tetrahydrofuran-3-yl)methylamine hydrochloride (Reference Production Example 3) and 20 ml of anhydrous tetrahydrofuran, 1.0 g of triethylamine was added at room temperature and: stirred for 30 minutes. To the mixed liquid, 0.63 g of (2E, 4E) -hepta-2 , 4-dienoic acid and 1.9 g of l-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride were added, and stirred for 4 hours at room temperature. Then, to the reaction mixture, water was added and extracted with ethyl acetate 2 times. The organic layer was washed with brine, and dried over anhydrous sodium sulfate, then, concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 0.75 g of (2E, 4E) -N- (tetrahydrofuran-3-ylmethyl) hepta-2, 4-dienamide of the formula :(hereinafter, referred to as The Present Compound (5)).( 5 )[0105]The Present Compound (5)1H NMR (GDC13) : delta ppm: 7.24-7.16 (1H, m) , 6.15-6.10 (2H, m) , 5.74 (1H, d) , 5.61 (1H, brs), 3.89 (1H, td) , 3.81 (1H, dd) , 3.74 (1H, q) , 3.55 (1H, dd) , 3.42-3.31 (2H, m) , 2.57-2.47 (1H, m) , 2.22-2.14 (2H, m) , 2.09-1.99 (1H, m) , 1.67-1.57 (1H, m) , 1.03 (3H, t)

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; MATSUO, Noritada; OHSHITA, Jun; WO2012/133861; (2012); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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

To tetrahydro-furan-3-ol (1.0 g, 11.4 mmol) in anhydrous dichloromethane (15 mL) with triethylamine (2.37 mL, 17.03 mmol), was added methane sulfonyl chloride (12.5 mmol) at 0 C. The reaction mixture was stirred at RT for 3.5 hours, diluted with dichloromethane (50 mL) and washed with water. The organic phase was dried (MgSO4) and evaporated in-vacuo to give methanesulfonic acid tetrahydro-furan-3-yl ester as light orange oil (1.68 g, 89%). A mixture of piperazine-1-carboxylic acid tert-butyl ester (1.0 g, 5.38 mmol), methanesulfonic acid tetrahydrofuran-3-yl ester (1.07 g, 6.45 mmol) and K2CO3 (2.96 g, 21.5 mmol) was stirred in anhydrous acetonitrile (50 mL) under reflux conditions for 12 hours. The reaction mixture was cooled and poured onto water and extracted with dichloromethane to give after silica chromatography, 4-(tetrahydro-furan-3-yl)-piperazine-l-carboxylic acid tert-butyl ester, as a colourless oil (0.57 g, 41%). NMR deltaH(400 MHz, CDCl3): 1.54 (s, 9H); 1.85-2.10 (m, 2H); 2.37-2.48 (m, 4H); 3.06 (m, IH); 3.46 (m, 4H); 3.67-3.97 (m, 4H).4-(Tetrahydro-furan-3-yl)-piperazine-l-carboxylic acid tert-butyl ester (0.57 g, 2.21 mmol) was BOC-deprotected as in Reference Example 3, to give, the title compound as a gummy residue (264 mg, 76%).

453-20-3 3-Hydroxytetrahydrofuran 9960, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; WO2009/53715; (2009); 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.

The raw material 12 – carbonyl oleanolic acid (189 mg, 0 . 40 mmol) is dissolved in anhydrous pyridine (3 ml) in, adding 2, 2 – dimethyl succinic anhydride (256 mg, 2 mmol), DMAP (49 mg, 0 . 40 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 202 mg, is compound 17, yield 68percent.

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; Chen Zhong; Duan Huaqing; Yang Shilin; Li Guoxiong; (26 pag.)CN109485688; (2019); A;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

915095-89-5,915095-89-5, (S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 2.90 g (S)-3-[4-(5-bromo-2-chloro-benzyl)-phenoxy]-tetrahydrofuran in 4 mL of THF at 0 to 20 C. (or alternatively at 20 C.), is slowly charged 8.4 mL of 1.0 M i-PrMgCl/LiCl in THF. The reaction is stirred at 20 C. for 16 hours and cooled to -23 C. 4.3 g of 2,3,4,6-tetrakis-O-(trimethylsilyl)-D-glucopyranone in 2 mL of THF is added dropwise. The reaction is then stirred at -20 C. for 2 h. Aqueous NH4Cl solution (25 weight-%, 12 mL) is added to quench the reaction. MTBE (8 mL) is added and the organic layer is separated. The aqueous layer is extracted with EtOAc (30 mL). The combined organic phases are dried over MgSO4 and concentrated.

915095-89-5 (S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran 15941217, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; Boehringer Ingelheim International GmbH; US2006/258749; (2006); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

97-99-4, (Tetrahydrofuran-2-yl)methanol is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,97-99-4

To a solution of (2R)-tetrahydrofuran-2-ylmethanol (58 mg, 0.57 mmol) in dry DMF (5 mL) was added NaH (23 mg, 60% in mineral oil, 0.57 mmol) under a N2 atmosphere. After the addition, the reaction mixture was stirred at room temperature for 1 hr. Then, to the mixture was added (2R)-2-[({2-chloro-6-[4-(1 /-/-pyrazolo[3,4-b]pyridin-3-yl)piperidin-1 -yl]pyrimidin-4- yl}carbonyl)amino]propyl benzoate (1-183) (100 mg, 0.19 mmol). After the addition, the resulting mixture was heated at 50 C for 4 hr. LCMS showed the reaction was completed. The mixture was cooled to room temperature and quenched with H20 (20 mL). The mixture was extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine (4 x 50 mL), dried over Na2S04 and concentrated to give the residue, which was purified by silica gel chromatography (CH2CI2/MeOH = 10/1 , Rf ~ 0.6) to give the crude product, which was further purified with preparative HPLC(Column: Phenomenex Gemini C18 250 x 21 .2 mm, deltamuetaiota. Mobile phase: from 20% MeCN (0.225% HCOOH) in water to 40% MeCN (0.225% HCOOH) in water. Wavelength: 220 nm) Lyophilization afforded N-[(2f?)-1 -hydroxypropan-2-yl]-6-[4-(1 H- pyrazolo[3,4-b]pyridin-3-yl)piperidin-1 -yl]-2-[(2R)-tetrahydrofuran-2-ylmethoxy]pyrimidine-4- carboxamide (Example 80) (20.1 mg, 22%) as a white solid. LCMS (APCI), m/z 482.2 [M + H]+; (400 MHz, DMSO-c/s) 8 ppm 13.29 (br. s., 1 H), 8.48 – 8.49 (m, 1 H), 8.31 (d, J = 8.0 Hz, 1 H), 8.18 (d, J = 8.8 Hz, 1 H), 7.13 -7.16 (m, 1 H), 7.04 (s, 1 H), 4.89 (t, J = 5.5 Hz, 1 H), 4.50 (br. s., 1 H), 4.26 (d, J = 5.5 Hz, 2 H), 4.12 – 4.18 (m, 1 H), 4.03 – 4.04 (m, 1 H), 3.77 – 3.82 (m, 1 H), 3.65 -3.70 (m, 1 H), 3.42 – 3.47 (m, 3 H), 3.16 – 3.23 (m, 2 H), 3.00 (br. s., 1 H), 2.12 (d, J = 1 1 Hz, 2 H), 1.96 – 2.04 (m, 1 H), 1 .81 -1 .88 (m, 4 H), 1 .62 – 1 .71 (m, 1 H), 1 .15 (d, J = 6.5 Hz, 3 H).

The synthetic route of 97-99-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PFIZER INC.; JOHNSON, Ted William; RICHARDSON, Paul Francis; COLLINS, Michael Raymond; RICHTER, Daniel Tyler; BURKE, Benjamin Joseph; GAJIWALA, Ketan; NINKOVIC, Sacha; LINTON, Maria Angelica; LE, Phuong Thi Quy; HOFFMAN, Jacqui Elizabeth; (335 pag.)WO2016/97918; (2016); 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.97-99-4,(Tetrahydrofuran-2-yl)methanol,as a common compound, the synthetic route is as follows.

97-99-4, Example 11; N-[(3E)-5-tert-butyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]isoxazol-3(2H)-ylidene]-5-chloro-2-methoxybenzamide; Example 11A; (2R)-tetrahydrofuran-2-ylmethyl 4-methylbenzenesulfonate; To (R)-(tetrahydrofuran-2-yl)methanol (1.0 g, 9.8 mmol) in CH2Cl2 (3 mL) and pyridine (3 mL) at ambient temperature was added 4-methylbenzene-1-sulfonyl chloride (2.0 g, 10.3 mmol) portion-wise over 5 minutes. This mixture was stirred for 16 hours at ambient temperature then was quenched with 10 mL of 5% aqueous HCl and was extracted with 3¡Á5 mL CH2Cl2. The combined organics were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (SiO2, 75% hexanes in ethyl acetate) to give the title compound (1.7 g, 6.8 mmol, 69% yield). MS (DCI/NH3) m/z 257 (M+H)+ and 274 (M+NH4)+.

As the paragraph descriping shows that 97-99-4 is playing an increasingly important role.

Reference£º
Patent; ABBOTT LABORATORIES; US2010/249129; (2010); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

17347-61-4, 2,2-Dimethylsuccinicanhydride is a Tetrahydrofurans compound,it involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy- 5a,5b,8,8,11a-pentamethyl-N-((5-phenyl-1H-imidazol-2-yl)methyl)-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxamide (0.6 g, 0.98 mmol, 1.0 eq) and 2,2-dimethyl succinic anhydride (0.5 g, 3.92 mmol, 4.0 eq) in toluene (12 mL) was added DMAP (0.239 g, 1.96 mmol, 2.0 eq). The reaction mixture was heated at 90 C for overnight. TLC indicated starting material was consumed and the desired product was observed. The mixture was concentrated under reduced pressure, cooled to 0 C, acidified to pH= 6-7 with 1N HCl and extracted with CH2CI2. The combined organic extracts were washed with water, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by silicagel column chromatography by using 60% EtOAc: n-Hexane as an eluent gave the desired product (0.13 g, 18% yield) as brown color solid. 1H MR (300 MHz, DMSO): delta 12.2 (bs, 1H), 11.66 (bs, 1H), 8.13-8.11 (m, 1H), 7.73 (d, J = 6.3 Hz, 2H), 7.32 (s, 1H), 7.3 (t, J = 6.9Hz, 2H), 7.17-7.14 (m, 1H), 4.64 (s, 1H), 4.52 (s, 1H), 4.37-4.22 (m, 4H), 3.05-2.98 (m, 1H), 2.31-2.18 (m, 2H), 1.91-1.61 (m, 6H), 1.6-1.21 (m, 18H), 1.09-0.96 (m, 8H), 0.92 (s, 3H), 0.81-0.63 (m, 12H). ES Mass: [M+l]+ 740.55. HPLC: 86.0%.

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

Reference£º
Patent; HETERO RESEARCH FOUNDATION; BANDI, Parthasaradhi Reddy; KURA, Rathnakar Reddy; GAZULA LEVI, David Krupadanam; ADULLA, Panduranga Reddy; NEELA, Sudhakar; MOGILI, Narsingam; (87 pag.)WO2017/21922; (2017); 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.453-20-3,3-Hydroxytetrahydrofuran,as a common compound, the synthetic route is as follows.

To a solution of tetrahydrofuran-3-ol (10 g, 113.5 mniol) in DCM (150 mL) was added MsCI (15.6 g, 136.2 mmoL) and TEA (23 g, 227 mmol). The reaction mixture was stirred at room temperature for 18 h. Water (100 mL) was added and the mixture was extracted with DCM(100 mL x 2). The combined organic layers was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the title compound (16 g, 85%) as a brown oil. 1H NMR (400 MHz, CDCJ3) 6 5.27-5.25 (m, I H), 4.00-3.83 (m, 4 H), 3.01 (s, 3 H), 2.23 -2.18 (m, 2H)., 453-20-3

453-20-3 3-Hydroxytetrahydrofuran 9960, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ROMERO, F. Anthony; MAGNUSON, Steven; PASTOR, Richard; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy; CRAWFORD, Terry; ALBRECHT, Brian, K.; COTE, Alexandre; TAYLOR, Alexander, M.; LAI, Kwong Wah; CHEN, Kevin, X.; BRONNER, Sarah; ADLER, Marc; EGEN, Jackson; LIAO, Jiangpeng; WANG, Fei; CYR, Patrick; ZHU, Bing-Yan; KAUDER, Steven; (0 pag.)WO2016/86200; (2016); A1;,
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

Under nitrogen atmosphere, to a mixture of (tetrahydrofuran-3-yl)-methanol represented by the following formula: (25 g) and pyridine (125 ml) was added p-toluenesulfonyl chloride (56 g) under ice-cooling, and the mixture wasstirred under ice-cooling for 4. hrs. Then, water was added to the reaction mixture, and the mixture was extracted twice with tert-butyl methyl ether. The organic layer was washed with 1 mol/L hydrochloric acid followed by saturated brine. The organic layer was dried over anhydrous sodiumsulfate, and then filtered. The filtrate was concentrated under reduced pressure to obtain a crude product (58 g) of tetrahydrofuran-3-ylmethyl p-toluenesulfonate represented by the following formula:, 124391-75-9

As the paragraph descriping shows that 124391-75-9 is playing an increasingly important role.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; MIYAZAKI, Hiroyuki; MATSUO, Noritada; OHSHITA, Jun; WO2013/47904; (2013); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

165253-29-2, 3-(Bromomethyl)tetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A solution of ethyl 2-oxocyclopentanecarboxylate 8a (0.50 mL, 3.4 mmol) and benzyl bromide (0.50 mL, 4.2 mmol) in N,N-dimethylacetamide (5 mL) is treated with powdered cesium carbonate (1.93 g, 5.9 mmol) and stirred at 65 ¡ãC overnight. The mixture is cooled, filtered, and concentrated in vacuo. Purification of the crude material by flash chromatography(hexanes/ethyl acetate gradient) affords ethyl 1-benzyl-2-oxocyclopentane carboxylate 8b as a clear oil., 165253-29-2

165253-29-2 3-(Bromomethyl)tetrahydrofuran 14173422, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Article; Azimioara, Mihai; Alper, Phil; Cow, Christopher; Mutnick, Daniel; Nikulin, Victor; Lelais, Gerald; Mecom, John; McNeill, Matthew; Michellys, Pierre-Yves; Wang, Zhiliang; Reding, Esther; Paliotti, Michael; Li, Jing; Bao, Dingjiu; Zoll, Jocelyn; Kim, Young; Zimmerman, Matthew; Groessl, Todd; Tuntland, Tove; Joseph, Sean B.; McNamara, Peter; Seidel, H. Martin; Epple, Robert; Bioorganic and Medicinal Chemistry Letters; vol. 24; 23; (2014); p. 5478 – 5483;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem