Heterocyclic Building Blocks-Tetrahydrofuran

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.,19311-37-6

4,4?-Di-tert-butyl-2,2?-bipyridine (16.10 mg, 0.06 mmol, 0.6 equiv.) and 1,2-dimethoxyethane -dichloronickel (1:1) (10.99 mg, 0.05 mmol, 0.5 equiv.) were charged under argon in a flask and suspended in dry 1 ,2-dimethoxyethane (10 ml). This mixture was sonicated for 5 mm. In a separated microwave vial under argon Iridium( 1+), [4,4?-bis( 1,1 -dimethylethyl)-2,2?-bipyridine-icNl ,icNl ?]bis [3,5- difluoro-2- [5-(trifluoromethyl)-2-pyridinyl-icN]phenyl-icC] -, (OC-6-3 3)-, hexafluorophosphate( 1-) (1:1) (CAS 870987-63-6) (5.61 mg, 5.00 jimol), N-[5-(7-bromo-4-oxoquinazolin-3(4H)-yl)-2- (trifluoromethoxy)phenyl] -1 -(4-methylpiperazin- 1 -yl)cyclopropanecarboxamide (56.6 mg, 100 jimol),and lithium hydroxide (4.79 mg, 200 jimol) were charged in a 2 mL vial. 1 mL of the nickel pre-catalyst solution was syringed into the vial containing the reaction mixture. The solution was degassed a second time by sparging with argon while stirring for 10 minutes. Under a constant flow of argon, 3- bromotetrahydrofurane (racemate) (14 jil, 150 jimol) and 1,1,1,3,3,3-hexamethyl-2- (trimethylsilyl)trisilane (31 jil, 100 jimol) were added to the reaction mixture using a Hamilton syringe.The reaction mixture was iffadiated with one 34 W blue LED lamp in the EvoluChemTM PhotoChemistry Device using the 8 x 2 mL vial rack which contains an incorportated fan for cooling to maintain the experiment at room temperature. The reaction mixture was then allowed to stir in the device for 15 hours. The reaction mixture was charged completely on a silica gel column and a chromatographic separation was performed with a gradient of dichloromethane/methanol from 100:0 to90:10. The material obtained was purified by preparative RP-HPLC on a 125x30mm column with acetonitrile/water (0.2% ammonia) to provide 10.0 mg (96 % purity, 17 % yield) of the title compound.LC-MS (Method 2): R = 1.88 mm; MS (ESIpos): m/z = 558 [M+H]1HNMR (500 MHz, DMSO-d6) [ppm]: -0.007 (1.09), 0.007 (0.77), 1.106 (1.50), 1.115 (4.03), 1.122 (4.31), 1.129 (1.98), 1.237 (1.98), 1.245 (4.44), 1.251 (3.60), 1.261 (1.50), 1.908 (0.53), 1.968 (0.47),1.983 (1.12), 1.992 (0.62), 1.999 (1.14), 2.008 (1.32), 2.014 (0.54), 2.024 (1.29), 2.039 (0.54), 2.194(16.00), 2.359 (0.43), 2.362 (0.50), 2.366 (0.46), 2.375 (0.89), 2.384 (1.03), 2.391 (1.41), 2.400 (1.97),2.406 (1.52), 2.409 (1.46), 2.415 (2.29), 2.425 (2.09), 2.431 (2.27), 2.453 (4.01), 2.519 (0.66), 2.523(0.54), 3.249 (1.47), 3.265 (1.68), 3.286 (1.08), 3.577 (0.40), 3.592 (1.13), 3.607 (1.72), 3.622 (1.37),3.636 (0.55), 3.651 (2.79), 3.667 (2.88), 3.681 (1.82), 3.813 (1.07), 3.828 (2.52), 3.844 (2.88), 3.859(1.21), 3.981 (1.12), 3.990 (1.19), 3.997 (2.06), 4.007 (2.02), 4.014 (0.95), 4.023 (0.88), 4.079 (2.08),4.094 (2.64), 4.095 (2.57), 4.110 (1.82), 7.374 (2.49), 7.379 (2.51), 7.391 (2.59), 7.396 (2.80), 7.528(2.04), 7.531 (2.08), 7.545 (2.10), 7.548 (2.20), 7.629 (3.95), 7.633 (3.60), 7.677 (1.95), 7.680 (1.86),7.691 (0.78), 7.694 (1.63), 7.697 (1.50), 8.127 (4.08), 8.143 (3.73), 8.352 (9.84), 8.365 (0.76), 8.584(4.25), 8.589 (4.19), 10.650 (3.53).

The synthetic route of 19311-37-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; JIMENEZ, NUNEZ, Eloisa; BORISSOFF, Julian; HAHN, Michael; DIETZ, Lisa; ZDENKA, GAUGAZ, Fabienne; BENDER, Eckhard; LANG, Dieter; GIESE, Anja; THEDE, Kai; ZORN, Ludwig; BOULTADAKIS ARAPINIS, Melissa; (190 pag.)WO2019/63708; (2019); 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.,453-20-3

To a solution of tetrahydro-furan-3-ol (9.0 g, 79 mmol) and triethyl amine (20 mL, 176 mmol) in THF (200 mL) was added methanesulfonyl chloride (12.9 g, 1 13 mmol) at 0C. The mixture was stirred overnight and then evaporated to dryness. The residue was extracted with EtOAc (3 x 300 mL) and washed with saturated, aqueous NaHC03. The organic layer was dried over Na2S04 and evaporated to dryness to give methanesulfonic acid tetrahydro-furan-3-yl ester as a yellow viscous liquid (12.4 g, 94%) which was used without further purification.

The synthetic route of 453-20-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; H. LUNDBECK A/S; ESKILDSEN, J¡ãrgen; WO2014/49133; (2014); 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.5061-21-2,2-Bromo-4-butanolide,as a common compound, the synthetic route is as follows.,5061-21-2

EXAMPLE VI 2-Azido-gamma-butyrolactone 1.56 g (10 mmol) of 2-bromo-gamma-butyrolactone are dissolved in 2 ml of dimethylformamide and treated at 0 C. with 612 mg (12.5 mmol) of lithium azide. The mixture is stirred at room temperature for 2 h, treated with water and extracted three times with methylene chloride. The combined organic phases are washed three times with water, dried over sodium sulphate and concentrated. 1.10 g (86.6% of theory) of the title compound are obtained. MS: 127

The synthetic route of 5061-21-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bayer Aktiengesellschaft; US6194428; (2001); B1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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

General procedure: Anhydrous K2CO3 (1 equiv.) was added to the solution of relevant amine (1 equiv.) in 20 mL of solvent (acetonitrile, DCM or Me2CO) and the mixture was stirred at room temperature for 0.5 h. Then a solution of 3-bromodihydrofuran-2(3H)-one (1 equiv.) in 5 mL of appropriate solvent was added dropwise and stirring was continued for 3-20 h. In the synthesis of compounds 11 and 12 tetrabutylammonium bromide (TBAB) (0.1 equiv.) was added. After the reaction was completed, the precipitate was filtered off and the filtrate was concentrated under vacuum. Obtained crude products were recrystallized from suitable solvent (solid) or purified by column chromatography (oil). Lactone 11 was isolated as a hydrochloride salt and recrystallized from DCM. Synthesis of compound 13 was described elsewhere [24] B. Malawska and S. Gobaille, Pharmazie 50 (1995), pp. 390-393. View Record in Scopus | Cited By in Scopus (10)[24].

The synthetic route of 5061-21-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Kulig, Katarzyna; Wickowski, Krzysztof; Wickowska, Anna; Gajda, Justyna; Pochwat, Bart?omiej; Hoefner, Georg C.; Wanner, Klaus T.; Malawska, Barbara; European Journal of Medicinal Chemistry; vol. 46; 1; (2011); p. 183 – 190;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

53662-85-4, Methyl tetrahydrofuran-3-carboxylate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,53662-85-4

To an ice-cooled solution of methyl tetrahydrofuran-3-carboxylate (50 g, 0.385 mol) and acetonitrile (47 g, 1.154 mol) in tetrahydrofuran (500 mL) was added potassium ieri-butoxide (129 g, 1.15 mol) portion- wise. The resulting mixture was warmed to room temperature and stirred for 1 h. The reaction mixture was poured into saturated aqueous ammonium chloride solution (1 L) and extracted with ethyl acetate (3 x 400 mL). The collected organic layers were washed with saturated aqueous sodium chloride solution (400 mL), dried over sodium sulfate, and concentrated in vacuo to afford product (41 g, crude, 76.6% yield).

The synthetic route of 53662-85-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; LIU, Wen; PATEL, Snahel; SIU, Michael; WO2014/111496; (2014); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

79-50-5, 3-Hydroxy-4,4-dimethyldihydrofuran-2(3H)-one is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,79-50-5

A mixture of 29.5 g of pantolactone, 300 mg of ruthenium (III) chloride, 400 ml of water and 200 ml of ethyl acetate was heated with stirring to reflux temperature by applying a microwave field generated from a microwave reactor (Ethos 1600, available from MLS GmbH, D-88299 Leutkirch im Allgau, Germany) having a power output of 700 W. 145.5 g of sodium (meta) periodate were added to the boiling mixture within 10 minutes. The reaction mixture was then stirred for a further 20 minutes and thereafter rapidly cooled. The organic phase was separated from the aqueous phase and the sodium iodate precipitate in the former phase filtered off by suction and washed five times with 20 ml quantities of ethyl acetate. The two-phase mixture was separated and the aqueous phase extracted twice with 50 ml of ethyl acetate. The combined organic phases were dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure. Ketopantolactone was thus obtained in a purity of 98% and a yield of 60% based on starting pantolactone. From the aqueous phase an additional 12% of product could be isolated. Unreacted pantolactone was recovered from the aqueous phase. Following this procedure an 80% conversion of the starting pantolactone into ketopantolactone and a selectivity of 0.95 could be achieved.

The synthetic route of 79-50-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ROCHE VITAMINS AG; WO2003/91235; (2003); 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

Example 1 : Lambda/-((2S)-5-{[(2/?)-tetrahydro-2-furanylmethyl]oxy}-2,3-dihydro-1H-inden-2- yl)-2-propanesulfonamide; To a solution of Lambda/-[(2S)-5-hydroxy-2,3-dihydro-1 H-inden-2-yl]-2-propanesulfonamide (300 mg, 1.175 mmol, Description 3) and (2R)-tetrahydro-2-furanylmethanol (0.125 ml, 1.292 mmol) in dichloromethane (6 ml) was added DIAD (0.228 ml, 1.175 mmol) followed by triphenylphosphine (308 mg, 1.175 mmol). The reaction mixture was stirred at 25 0C overnight. 75 mul of (2/?)-tetrahydro-2-furanylmethanol, 0.115 ml of DIAD and 150 mg of triphenylphosphine were added to the reaction mixture which was stirred at room temperature overnight again.Solvent was removed and the residue was partitioned between water (10 ml) and EtOAc (30 ml). The aqueous phase was further extracted with EtOAc (30 ml). Organics were dried over MgSO4 and concentrated to give crude product which was purified by reverse phase chromatography using the MDAP. Relevant fractions were combined and concentrated to give the title compound as a white solid (170 mg).LC/MS (ES): Found 340 (ES+), retention time 0.97 mins (2 minute method). C17H25NO4S requires 339.1H NMR (400 MHz, MeOH-d4) delta 1.35 (d, J=6.8 Hz, 6 H), 1.69 – 1.85 (m, 1 H), 1.86 – 2.14(m, 3 H), 2.73 – 2.93 (m, 2 H), 3.10 – 3.28 (m, 3 H), 3.76 – 3.84 (m, 1 H), 3.85 – 3.97 (m, 3H), 4.16 (quintet, J=7.5 Hz, 1 H), 4.19 – 4.26 (m, 1 H), 6.73 (dd, J=8.0, 2.4 Hz, 1 H), 6.78(s, 1 H), 7.06 (d, J=8.3 Hz, 1 H).

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

Reference£º
Patent; GLAXO GROUP LIMITED; WARD, Simon, E; BERTHELEME, Nicolas; WO2010/37760; (2010); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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 53 (0368) Ethyl 3-butyl-1,2,4-oxadiazole-5-carboxylate (0.40 g, 2 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (2.75 g, 20 mmol) and diisopropylethylamine (2.58 g, 20 mmol) were added to ethanol (40 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, then water was added to the residue, and the mixture was extracted three times 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 0.43 g of N-(tetrahydrofuran-3-ylmethyl)-3-butyl-1,2,4-oxadiazole-5-c arboxamide (hereinafter, referred to as Compound of Present Invention (58)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)):0.96(3H, t), 1.36-1.46(2H, m), 1.64-1.79(3H, m), 2.07-2.16(1H, m), 2.58-2.65(1H, m), 2.79(2H, t), 3.45-3.55(2H, m), 3.62(1H, dd), 3.74-3.81(1H, m), 3.85(1H, dd), 3.93(1H, td), 7.19(1H, brs)

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
Tetrahydrofuran | (CH2)3CH2O – PubChem

86087-24-3, (R)-Tetrahydrofuran-3-ol is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 : Synthesis of [(3R)-Tetrahydrofuran-3-yl] 4-methylbenzenesulfonateTo a solution of 25.43 g (R)-tetrahydro-furan-3-ol in 60 mL pyridine and 250 mL DCM was added 73.0 g of 4-methyl-benzenesulfonyl chloride followed by 1 .0 g N,N-dimethylpyridin-4- amin. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with DCM and washed with 2M hydrochloric acid and water. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (DCM ->DCM : methanol 95:5) to yield 59.46 g [(3R)-tetrahydrofuran-3-yl] 4-methylbenzenesulfonate as oil.Analysis: MS: M+H = 243

86087-24-3 (R)-Tetrahydrofuran-3-ol 641512, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; DAHMANN, Georg; HOFFMANN, Matthias; KLICIC, Jasna; LAMB, David James; MCCARTHY, Clive; NAPIER, Spencer; PARRISH, Karen; SCOTT, John; SWANTEK FITZGERALD, Jennifer L.; WALKER, Edward; WO2015/140054; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

111769-27-8, (R)-Tetrahydrofuran-3-amine 4-methylbenzenesulfonate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 244 : (R)- l-(5,6-dichloro- 1-p-tolyl- lH-benzo [d] imidazol-2-yl)-7V-(tetrahydrofuran- 3-yl)piperidine-4-carboxamideEthyl l-(5,6-dichloro-lH-benzo[d]imidazol-2-yl)piperidine-4-carboxylate (110 mg, 0.321 mmol) dimethylsulfoxide (1 mL), caesium carbonate (147 mg, 0.45 mmol), l-iodo-4-methylbenzene (140 mg, 0.643 mmol), 8-hydroxyquinoline (9.3 mg, 0.064 mmol), polyethylene glycol 400 (64.3 mg, 0.161 mmol) and copper(I) oxide (4.6 mg, 0.032 mmol) was subjected to microwave conditions for one hour at 15O0C. The reaction mixture was diluted with N,N-dimethyl- formamide (4 mL), filtered and the filtrate concentrated in vacuo. The residue was dissolved in ethanol (4 mL) and aqueous sodium hydroxide (2 mL, 1 N), and stirred at room temperature over the weekend. The reaction mixture was treated with aqueous hydrochloric acid (1 mL, 2 N) and concentrated. The residue was mixed with N,N-dimethylformamide (13 mL), N,7V-diisopropyl- ethylamine (Hunig’s base, DIEA, 19.2 mg, 0.148 mmol), 2-(7-aza-lH-benzotriazole-l-yl)-1,1,3,3-tetramethyluronium hexafluoro-phosphate (EtaATU, 14.1 mg, 0.037 mmol) and (R)-(+)- tetrahydrofuran-3 -amine 4-methylbenzenesulfonate (9.6 mg, 0.0371 mmol). The reaction mixture was stirred at room temperature for 2 hours, concentrated in vacuo and purified on hplc (preparative RP-LC was performed on a Gilson system equipped with a Zorbax SB-C8 (5 mum, 21.2 x 150 mm) column, using methano I/water (0.05% formic acid) gradients at a flow rate of 4 niL/min with UV (214 or 254 nm) and MS (ESI) detection) to give 7.7 mg of (R)- 1 -(5,6- dichloro- 1 -p-tolyl- lH-benzo[d]imidazol-2-yl)-N-(tetrahydrofuran-3-yl)piperidine-4- carboxamide. LC-MS (m/z) 473.1 (M+ 1).

The synthetic route of 111769-27-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVASAID AB; WANNBERG, Johan; ALTERMAN, Mathias; MALM, Johan; STENBERG, Patric; WESTMAN, Jacob; WALLBERG, Hans; WO2011/23812; (2011); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem