Heterocyclic Building Blocks-Tetrahydrofuran

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.

The mixture of triethylamine (6.4 mL, 45.53 mmol), TsCl (6.4 g, 33.39 rnrnol) and 185 mgof DMAP were combined in CH2Clz (70 mL). this solution was cooled in an ice bath andto it was added a solution of tetrahydrofurfuryl alcohol Sa (3.1 g, 30.35 mmol) in 30 mL ofCH2Clz over 20 min. the reaction stirred overnight and was then concentrated in vacuum,the residue was taken up in ethyl acetate and then washed 2 times with a saturated solutionof NaHC03 and once with a brine. The organic layers were dried over MgS04, filtered andconcentrated in vacuum. The crude product was purified by Column chromatography onsilica gel (CH2Clz/cHex: 50/50) to give the expected product as oil (m = 5.6 g, 72 %). 1HNMR (300 MHz, CDCb): () (ppm) 1.48-1.68 (m, lH), 1.71-2.05 (m, 3H), 2.40 (s, 3H),3.58-3.82 (m, 2H), 3.86-4.15 (m, 3H), 7.31 (d, J = 8.0 Hz, 2H), 7.75 (d, J = 8.2 Hz, 2H).MS: [M+Ht rnlz = 257, 97-99-4

97-99-4 (Tetrahydrofuran-2-yl)methanol 7360, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; UNIVERSITE DE LILLE 2 DROIT ET SANTE; INSTITUT PASTEUR DE LILLE; INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE); CHARTON, Julie; DEPREZ, Benoit; BOULAHJAR, Rajaa; LEROUX, Florence; HOGUET, Vanessa; STAELS, Bart; MUHR-TAILLEUX, Anne; HENNUYER, Nathalie; BELLOY, Loic; (92 pag.)WO2017/134188; (2017); A1;,
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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 19 (0330) 5-Cyclopentyloxymethylisoxazole-3-carboxylic acid (0.26 g, 1.2 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (0.20 g, 1.5 mmol), triethylamine (0.15 g, 1.5 mmol) and 1-hydroxybenzotriazole (0.02 g, 0.15 mmol) were added to chloroform (amylene addition product) (15 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.28 g, 1.5 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 0.10 g of N-(tetrahydrofuran-3-ylmethyl)-5-cyclopentyloxymethylisoxaz ole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (19)) represented by the following formula. 1H-NMR (CDCl3, TMS, delta(ppm)): 1.54-1.59(2H, m), 1.68-1.72(7H, m), 2.04-2.13(1H, m), 2.56-2.58(1H, m), 3.46(2H, t), 3.57-3.60(1H, m), 3.75-3.78(1H, m), 3.84-3.94(-2H, m), 4.03-4.04(1H, m), 4.58(2H, s), 6.69(1H, s), 6.93(1H, br s)

184950-35-4, 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;,
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17347-61-4, 2,2-Dimethylsuccinicanhydride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Compound 5 (16 mg, 0.032 mmol), 2,2-dimethyl succinic anhydride(41 mg, 0.32 mmol), DMAP (8 mg, 0.064 mmol), and pyridine (1.5 mL)were placed in a 10 mL glass tube and sealed. The mixture was stirred at120 C for about 12 h. The reaction mixture was then transferred into a50 mL flask. Pyridine was removed under reduced pressure. HCl (3 N,10 mL) was added, the mixture was extracted three times with EtOAc,and the organic layer washed with 3 N HCl for a second time. Then theorganic layer was washed with brine, dried over anhydrous Na2SO4,and concentrated in vacuo. The residue was purified by silica gelcolumn chromatography (hexane/EtOAc as eluent) to provide targetproduct 7 (11 mg). White solid, yield: 54%.

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; Li, Jizhen; Chang, Ling-Chu; Hsieh, Kan-Yen; Hsu, Pei-Ling; Capuzzi, Stephen J.; Zhang, Ying-Chao; Li, Kang-Po; Morris-Natschke, Susan L.; Goto, Masuo; Lee, Kuo-Hsiung; Bioorganic and Medicinal Chemistry; vol. 27; 13; (2019); p. 2871 – 2882;,
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.88675-24-5,Tetrahydrofuran-3-amine,as a common compound, the synthetic route is as follows.

To a solution of 4-chloropyrrolo[l,2-b]pyridazine-3-carbonitrile (15g) (0.15 g, 0.84 mmol) in DMF (2 mL) was added at room temperature tetrahydrofuran-3-amine (53a) (0.22 mgs, 2.52 mmol), DIPEA (0.87 mL, 5 mmol) and stirred at room temperature overnight. The reaction was quenched with water (10 mL) and extracted with ethyl acetate (10 mL). The aqueous layer was separated and extracted with ethyl acetate (2 x 10 mL). The organic layers were combined washed with water (2 x 10 ml), brine (10 mL), dried, filtered and concentrated in vacuum. The residue obtained was purified by flash column chromatography (silica gel 12g, eluting with 0-100% ethyl acetate in hexanes) to furnish 4-(tetrahydrofuran-3- ylamino)pyrrolo[l,2-b]pyridazine-3-carbonitrile (53b) (0.175 g, 91%) as a tan solid; 1H NMR (300 MHz, DMSO) d 7.95 (s, IH), 7.89 (d, J = 7.0, IH), 7.71 (dd, J = 1.6, 2.6, IH), 7.24 (dd, J = 1.6, 4.5, IH), 6.69 (dd, J = 2.7, 4.4, IH), 4.86 (dt, J = 3.6, 11.1, IH), 4.01 – 3.83 (m, 3H), 3.76 (td, J = 5.8, 8.3, IH), 2.39 – 2.23 (m, IH), 2.15 (m, IH); IR (KBr) 2194 cm-1; MS (ES-) 227.0(M-I) 262.9 (M+Cl); Analysis: Calcd for C12H12N4O? 0.25 H2O: C, 61.92; H, 5.41; N, 24.07; Found: C, 62.05; H, 5.23; N, 24.01., 88675-24-5

The synthetic route of 88675-24-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda S.; KOTIAN, Pravin L.; KUMAR, V. Satish; WU, Minwan; LIN, Tsu-Hsing; WO2011/14817; (2011); A1;,
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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

57595-23-0, To a solution of methyi-4-oxo-tetrahydrofuro-3-carboxylate (1.0 g, 6.94 mmol) in ethanol (16 niL) was added 4-bromobenzylamme (1.621 g5 7.29 mmol) followed by triethylamine (0.919 niL, 6.59 mmol) and acetic acid (0.119 mL, 2.082 mmol). The mixture was refluxed for 2 h. The mixture was concentrated in vacuo, taken up in EtOAc (30 mL) and water (30 mL). The organic layer was then washed with saturated NaHCC>3 (20 mL). The aqueous layer was then extracted with EtOAc (3 x 40 mL) and the combined organic extracts were washed with water (30 mL) and brine (30 mL), dried over Na2SC>4 and concentrated in vacuo to give a brown oil which solidified over time to an oily brown solid, which was taken on crude to the next reaction.

57595-23-0 Methyl 4-oxotetrahydrofuran-3-carboxylate 14666564, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK & CO., INC.; WO2009/108496; (2009); 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, The synthesis was conducted in flow. Reagent solution A contained 4-(4-chlorophenyl)isoquinoline-6-carboxylic acid (8 mg, 28.2 11mol), 0-(benzotriazol-1-yl)- N,N,N’,N’-tetramethyluronium tetrafluoroborate (TBTU, 10.9 mg, 33.8 11mol) and N,N diisopropylethylamine (10.9 mg, 14.8 111, 84.6 11mol) in dimethylformamide (230 Ill) and reagent solution B contained tetrahydrofuran-3-ylamine (106 111 of a 0.4 M stock solution in dimethylformamide, 42.3 11mol) in dimethylformamide (144 Ill). The two reagent solutions were injected (0.250 mL of each solution) by means of Gilson LH 215 auto-sampler into the reactor sample loops (Gilson 819). Then, both reagent streams were combined at aT-piece connectorand the reagent mixture heated at 120 ¡ãC for 5 min in a 10 ml PFA tube reactor coil. The crude product stream was purified in-line by preparative HPLC (C18 reverse phase, acetonitrile I water (0.05 percenttriethylamine)= 2:98 to 98:2) to yield the title compound as a colorless oil (2.2 mg,16 percent). MS: m/e = 353.4 [M+Ht.

The synthetic route of 88675-24-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CECCARELLI, Simona M.; JAGASIA, Ravi; JAKOB-ROETNE, Roland; MARTIN, Rainer E.; WICHMANN, Juergen; WO2014/177596; (2014); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

87219-29-2,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.87219-29-2,(S)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

REFERENTIAL EXAMPLE 194 tert-Butyl (3S)-5-oxotetrahydro-3-furanylcarbamate: di-tert-Butyl dicarbonate (4.1 g) and 10% palladium on carbon (0.4 g) were added to a solution of benzyl (3S)-(-)-tetrahydro-5-oxo-3-furanylcarbamate (3.3 g) in tetrahydrofuran (20 ml), and the mixture was stirred for a day in a hydrogen atmosphere. After insoluble matter was filtered through Celite pad, the filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1) to obtain the title compound (1.5 g). 1H-NMR (CDCl3) delta: 1.45(9H,s), 2.45(1H,dd,J=17.8, 2.7 Hz), 2.86(1H,dd,J=17.8, 7.3 Hz), 4.12-4.23(1H,m), 4.54-4.62(2H,m), 4.85-4.95(1H,m).

The synthetic route of 87219-29-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; US2005/20645; (2005); 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.915095-89-5,(S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran,as a common compound, the synthetic route is as follows.

915095-89-5, (3S) -3- [4-[(2-chloro-5-iodophenyl) methyl] phenoxy] tetrahydrofuran (1.0 g, 2.72 mmol), tetrahydrofuran (16 mL),PMDTA (1.2mL, 1.5equiv) was added to a 250mL three-necked bottle in sequence, and after replacing the air in the reaction bottle with nitrogen,The temperature of the cold trap is controlled at about -78 C, and 2.5M n-butyllithium (1.6mL, 1.5equiv) is slowly added dropwise and stirred for about 1h.TMS-protected gluconolactone 4 (1.5 g, 1.3 equiv) and toluene (16 mL) were added to another 50 mL round bottom flask and mixed well, and the temperature of the cold trap was controlled at about -78 C.The toluene solution of 4 was slowly dropped into a three-necked flask, keeping the temperature unchanged, and stirred for 2h.Keeping the temperature unchanged, methanol (10 mL) was slowly dropped into a three-necked flask and stirred for 20 min.Then the temperature rose to about -20 C, and a 15% citric acid aqueous solution (50 mL) was slowly dropped into the three-necked flask. After the drop was completed, the temperature was raised to room temperature and stirred for 2 hours.Then, a saturated sodium bicarbonate aqueous solution (100 mL) was slowly dropped into a three-necked flask, and the drop was completed, and stirred for 20 min.Transfer the reaction solution to a 250mL separatory funnel, let stand for layer separation, separate the organic phase, and extract the aqueous phase with ethyl acetate,The organic phases were combined and washed three times with brine, and the organic phase was dried over anhydrous magnesium sulfate.After filtering off the desiccant, the solvent was removed by rotary evaporation to obtain a yellow oil.

As the paragraph descriping shows that 915095-89-5 is playing an increasingly important role.

Reference£º
Patent; Shenyang Pharmaceutical University; Ren Xuhong; Zhang Letian; (8 pag.)CN111040000; (2020); 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.696-59-3,2,5-Dimethoxytetrahydrofuran,as a common compound, the synthetic route is as follows.

696-59-3, General procedure: Oxone (0.09 g, 0.30 mmol) was added to a solution of the aromatic primary amines (2.5 mmol) and 2,5-dimethoxytetrahydrofuron (3.0 mmol) in a solvent (5 mL) was further added (Scheme1). The reaction mixture was heated under microwave irradiation for 10 min at 110 ¡À 10 C. The reaction mixture was irradiated until total consumption of the amine was verified by TLC. Water was added and the products were extracted with EtOAc (3×20 mL). The organic phasewas dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. The product was purified on a silica gel column chromatography eluted with mixture of ethylacetate/hexane (1:4) to afford the product.

696-59-3 2,5-Dimethoxytetrahydrofuran 79098, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Article; Gullapelli, Kumaraswamy; Brahmeshwari; Ravichander; Bulletin of the Chemical Society of Ethiopia; vol. 33; 1; (2019); p. 143 – 148;,
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52079-23-9, (S)-(-)-alpha-Hydroxy-gamma-butyrolactone is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5- (2-aminoethoxy)-N- [3-chloro-4- (pyridin-2-ylmethoxy) phenyl] quinazolin-4-amine (obtained as described in Example 2.6, preparation of starting materials, 0.5 g, 1.19 mmol) was heated to 130C in xylene (20 ml) until it had dissolved. (S)- (-)-a-hydroxy-y- butyrolactone (0.10 ml, 1.31 mmol) was added and the mixture was stirred at 130C for 3 hours. More (S)-(-)-oc-hydroxy-y-butyrolactone (0.05 ml, 0.66 mmol) was added and the mixture was heated for a further 2 hours. The resultant precipitate was filtered off while the mixture was hot, washed with diethyl ether (3 x 10 ml) and dried to give the title compound as a solid (430 mg, 69%) ; NMR spectrum (DMSO-d6) 1.38-1. 55 (m, 1H), 1.69-1. 85 (m, 1H), 3.37-3. 50 (m, 2H), 3.61-3. 77 (m, 2H), 3.89-4. 00 (m, 1H), 4. 28-4. 45 (m, 3H), 5.29 (s, 2H), 5.51 (d, 1H), 7.13 (d, 1H), 7.22 (d, 1H), 7.28-7. 41 (m, 2H), 7.49-7. 62 (m, 2H), 7.71 (t, 1H), 8.01 (d, 1H), 8.14-8. 25 (m, 1H), 8.45 (s, 1H), 8. 59 (d, 1H), 9. 82 (s, 1H) ; Mass spectrum MU 523.9, 52079-23-9

52079-23-9 (S)-(-)-alpha-Hydroxy-gamma-butyrolactone 357853, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/51923; (2005); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem