Heterocyclic Building Blocks-Tetrahydrofuran

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.124391-75-9,(S)-(Tetrahydrofuran-3-yl)methanol,as a common compound, the synthetic route is as follows.

A suspension of magnesium bromide (2 eq/mole, 108.17 g) in acetonitrile (300 ml) is added, at 0C, with acetic anhydride (4 eq/mole, 119.95 g). The mixture is left under stirring for 15 minutes at 0C, then 3-hydroxymethyl tetrahydrofuran (30 g, 293 mmoles) is added. The mixture is kept at the reflux temperature until complete disappearance of the substrate (18 h), then is added with 300 ml of a sodium bicarbonate saturated solution and left under stirring at room temperature for 30 minutes. The mixture is extracted with ethyl acetate (3×100 ml), the organic phase is dried over anhydrous sodium sulfate, filtered and the solvent is evaporated off to a residue. The reaction conversion is quantitative. 59.02 g (yield: 75%) of a colourless oil are obtained. The gas-chromatographic and nuclear magnetic resonance analysis of the residue show the presence of a mixture consisting of 2-acetoxymethyl-4-bromo-butyl-1-acetate and its 2-bromomethyl-4-acetoxybutyl-1-acetate isomer in a yield of 90% (53.12 g) and 10% (5.902 g), respectively. This mixture can be used directly in the subsequent reaction for the alkylation of 2-aminochloropurine (IV) as no addition products due to the presence of the minor isomer are formed. (The two isomers can anyway be separated, if necessary, by fractional distillation).2-Acetoxymethyl-4-bromo-butyl-1-acetate:1H-NMR (d, ppm): 1.83 (q, 2H, CH2) 1.98 (s, 6H, 2(CH3)) 2.07-2.13 (m, 1H, CH) 3.45 (t, 2H, CH2Br) 4.04 (d, 4H, 2(CH2O)).13C-NMR (d, ppm): 21.33 (CH2Br) 31.03(2(CH3)) 32.01 (CH2) 36.55 (CH) 64.00 (2(CH20)) 171.37 (2(CO)).2-Bromomethyl-4-acetoxy-butyl-1-acetate:1H-NMR (d, ppm): 1.63 (m, 2H, CH2) 1.88 (s, 3H, CH3) 1.90 (s, 3H, CH3) 1.99 (m, 1H, CH) 3.37 (d, 2H, CH2Br) 4.01 (d, 2H, CH2O) 4.13 (t, 2H, CH2O).13C-NMR (d, ppm): 20.55 (CH3) 21.03 (CH3) 28.37 (CH) 34.49 (CH2Br) 36.03 (CH2) 61.25 (OCH2) 66.26 (OCH2) 170.39 (CO) 170.42 (CO).

124391-75-9, 124391-75-9 (S)-(Tetrahydrofuran-3-yl)methanol 40784875, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; RECORDATI S.A.; WO2004/7418; (2004); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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

88675-24-5, Step-a: Synthesis of 3-Nitro-N-(tetrahydrofuran-3-yl)benzamide Tetrahydrofuran-3-amine (0.1 g, 1.148 mmol) and 3-nitrobenzoic acid (0.192 g, 1.148 mmol) were taken in pyridine (2 ml), to the mixture EDC.HCl (0.220 g, 1.148 mmol) was added, the reaction mixture was stirred under nitrogen for 10 hrs at room temperature. The reaction mixture was diluted with cold water (15 ml), extracted with ethyl acetate (2*10 ml). Combined organic layer was washed with satd. aq. sod bicarbonate and dil HCl, the organic layer was dried over sodium sulfate and concentrated under vacuum to afford the title product (240 mg). 1HNMR (400 MHz, CDCl3): delta 8.62-8.61 (m, 1H), 8.39-8.36 (m, 1H), 8.19-8.17 (m, 1H), 7.67 (t, 1H, J=8 Hz), 6.62 (d, 1H, J=6 Hz), 4.79-4.75 (m, 1H), 4.08-4.00 (m, 1H), 3.93-3.83 (m, 3H), 2.44-2.37 (m, 1H), 2.01-1.98 (m, 1H).

As the paragraph descriping shows that 88675-24-5 is playing an increasingly important role.

Reference£º
Patent; Dave, Bhavesh; Banerjee, Rakesh Kumar; Phukan, Samiron; Khoje, Abhijit Datta; Hangarge, Rajkumar; Jadhav, Jitendra Sambhaji; Palle, Venkata P.; Kamboj, Rajender Kumar; US2015/133424; (2015); 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

Example 85B (tetrahydrofuran-3-yl)methyl 4-methylbenzenesulfonate To a solution of (tetrahydrofuran-3-yl)methanol (5.15 g, 50.4 mmol) in dichloromethane (200 mL) were added triethylamine (21.08 mL, 151 mmol) and p-toluenesulfonyl chloride (9.61 g, 50.4 mmol) and the mixture was stirred at room temperature overnight. The reaction mixture was washed with water (100 mL) and brine (100 mL). The organic layer was dried with sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography using an Analogix Intelliflash280 (SiO2, 0-40% ethyl acetate in hexane) to provide the title compound (12.5 g, 97%) as colorless viscous liquid. 1H NMR (300 MHz, DMSO-D6) delta ppm 1.40-1.51 (m, 1H) 1.83-1.95 (m, 1H) 2.43 (s, 3H) 3.28-3.31 (m, 1H) 3.31-3.37 (m, 1H) 3.51-3.67 (m, 3H) 3.90-4.00 (m, 2H) 7.48-7.51 (m, 2H) 7.78-7.82 (m, 2H); MS (DCI/NH3) m/z 274 (M+NH4)+.

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

Reference£º
Patent; ABBOTT LABORATORIES; US2009/105306; (2009); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem