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.

97-99-4, Example 45; N-{(3E)-5-tert-butyl-1-methyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2-dihydro-3H-pyrazol-3-ylidene}-5-chloro-2-methoxybenzamide; Example 45A; (R)-((tetrahydrofuran-2-yl)methyl)hydrazine dihydrochloride; To (R)-(tetrahydrofuran-2-yl)methanol (4.0 g, 39.2 mmol), di-tert-butyl hydrazine-1,2-dicarboxylate (3.64 g, 15.67 mmol) and triphenylphosphine (15.41 g, 58.7 mmol) in THF (100 mL) was added (E)-di-tert-butyl diazene-1,2-dicarboxylate (13.5 g, 5.87 mmol). The mixture was stirred at ambient temperature for 3 h then diluted with water and extracted with EtOAc (100 mL¡Á2). The organic extract was washed with brine and concentrated. Purification by flash chromatography (silica gel, 5-30% EtOAc/hexane) afforded 10.2 g (82%) of (R)-di-tert-butyl 1-((tetrahydrofuran-2-yl)-methyl)-hydrazine-1,2-dicarboxylate, which was dissolved in a solution of 4M HCl in dioxane (40 mL) and stirred at ambient temperature overnight. The solvent was removed under reduced pressure and ethyl acetate (20 mL) was added with stirring. The solid precipitate was filtered, washed with ether (10 mL) and dried under vacuum to yield 7.8 g (97%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) delta ppm 1.48-1.63 (m, 1H), 1.73-1.88 (m, 2H), 1.90-2.02 (m, 1H), 2.84-3.01 (m, 2H), 3.61-3.71 (m, 1H), 3.72-3.83 (m, 1H), 3.97-4.08 (m, 1H), 5.76 (br, 5H); MS (ESI) m/z 117 (M+H)+.

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

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 52 (0367) 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) were added to chloroform (amylene addition product) (16 mL). 1-Ethyl-3-(3-dimetrylaminopropyl) carbodiimide hydrochloride (1.83 g, 12 mmol) was added to the mixture at room temperature, and the mixture was stirred overnight. Then, water was added thereto, and the mixture was extracted three times with chloroform. 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 0.76 g of N-(tetrahydrofuran-3-ylmethyl)-5-butyl-1,2,4-oxadiazole-3-c arboxamide (hereinafter, referred to as Compound of Present Invention (57)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)):0.96(3H, t), 1.38-1.49(2H, m), 1.62-1.73(1H, m), 1.80-1.87(2H, m), 2.05-2.15(1H, m), 2.55-2.67(1H, m), 2.95(2H, t), 3.45-3.55(2H, m), 3.61(1H, dd), 3.73-3.80(1H, m), 3.85(1H, dd), 3.92(1H, td), 7.10(1H, brs), 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;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

149809-43-8, ((3R,5R)-5-((1H-1,2,4-Triazol-1-yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methyl 4-methylbenzenesulfonate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example -3: Preparation of 4-(4-(4-(4-(((3R,5R)-5-((lH-l,2,4-triazol-l-yl)methyl)-5- (2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)phenyl)piperazin-l-yl)phenyl)-l- ((2S,3S)-2-(benzyloxy)pentan-3-yl)-lH-l,2,4-triazol-5(4H)-one of the structural formula (III) of crystalline Form B-3 l-((2S,3S)-2-(benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-l-yl)phenyl)- lH-l,2,4-triazol-5(4H)-one (4.0 Kg, 1.0 eq.) of the structural formula (II) was dissolved in Dimethyl sulfoxide (6.0 vol.) at 25¡À2C under nitrogen and cooled to 15-20 C. 25% aqueous sodium hydroxide solution (1.3 eq.) was added to the reaction mixture and was stirred for 10 minutes. ((3S,5R)-5-((lH-l,2,4-triazol-l-yl)methyl)-5-(2,4- difluorophenyl)tetrahydrofuran-3-yl)methyl 4-methylbenzenesulfonate of the structural formula (I) (4.02 Kg) was added to the reaction mixture and continued to stir for lh at 15- 20 C. Reaction temperature was raised to 28¡À2C and stirred for 45-50 h. Ethyl acetate (5.0 vol.) was added to the reaction mass and cooled to 15-20 C followed by addition of water (5.0 vol.), reaction mass was slowly warmed to 25¡À2C and stirred. Layers were separated; organic layer was collected. Aqueous layer was again extracted with Ethyl acetate (3 vol.). Combined organic layers were washed with water (3 vol.) and organic layer was concentrated partially to contain 5.0 Vol. of Ethyl acetate. Cooled the partially concentrated solution to 25¡À2C and was added n-Heptane (5.0 vol.), stirred at 28¡À2C for 30 min and further diluted with n- Heptane (2.0 vol.) heated to 42¡À2C, stirred for 30 min and then slowly cooled to 28¡À2C and continue to stir at 28¡À2C for 2h. The above mixture was cooled to 0-5 C and stirred for lh. Solid was filtered; washed with Heptane (5 vol.). Dried under VTD at 60+5 C to yield 4-(4-(4-(4-(((3R,5R)-5-((lH-l,2,4-triazol- 1 -yl)methyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methoxy)phenyl)piperazin- 1 – yl)phenyl)-l-((2S,3S)-2-(benzyloxy)pentan-3-yl)-lH-l,2,4-triazol-5(4H)-one of the structural formula (III) of crystalline Form B-3 with 96% yield. Characteristic Physico-Chemical Data of Crystalline Form B-3 of the Compound of Structural Formula III Physical appearance: Off-white to white solid X-ray Powder Diffraction Pattern: See Figure 3 and Table 3 DSC: See Figure 4 IR: See Figure 5

149809-43-8, The synthetic route of 149809-43-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BIOCON LIMITED; CHARYULU, Palle, Venkata, Raghavendra; GOWDA, Dharshan, Jakkali, Chandre; RAJMAHENDRA, Shanmughasamy; RAMAN, Manikandan; (41 pag.)WO2017/51342; (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.16874-33-2,Tetrahydrofuran-2-carboxylic acid,as a common compound, the synthetic route is as follows.

General procedure: To a mixture of 26b (100 mg, 0.28 mmol), 3-methoxypropionic acid (31.4 muL, 0.33 mmol), HOBt¡¤H2O (45.2 mg, 0.33 mmol) and Et3N (97 muL, 0.70 mmol) in THF (1.4 mL) was added WSC¡¤HCl (64.1 mg, 0.33 mmol). The mixture was stirred at room temperature for 3 h, and then poured into water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, Hexane/EtOAc) to give (6R,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((3-methoxypropanamido)methyl)-1,4-oxazepane-4-carboxylate (81 mg, 65percent) as a colorless oil.

16874-33-2, The synthetic route of 16874-33-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Yukawa, Tomoya; Fujimori, Ikuo; Kamei, Taku; Nakada, Yoshihisa; Sakauchi, Nobuki; Yamada, Masami; Ohba, Yusuke; Ueno, Hiroyuki; Takiguchi, Maiko; Kuno, Masako; Kamo, Izumi; Nakagawa, Hideyuki; Fujioka, Yasushi; Igari, Tomoko; Ishichi, Yuji; Tsukamoto, Tetsuya; Bioorganic and Medicinal Chemistry; vol. 24; 14; (2016); p. 3207 – 32174;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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

Step 6: Synthesis of 4-(lR,3aS,5aR,5bR,7aR,9S, l laR,l lbR,13aR,13bR)-3a-((R)-2-(5-(4- chloro phenyl)- 1 H-imidazo l-2-yl)pyrro lidine- 1 -carbonyl)-5 a,5b, 8 ,8,11 a-pentamethyl- 1 – (prop- 1 -en-2-yl) icosahydro- 1 H-cyclopenta[a]chrysen-9-yl)oxy)-2,2-dimethyl-4-oxobutanoic acid: [0225] To a stirred solution of (R)-2-(5-(4-chlorophenyl)-lH-imidazol-2- yl)pyrrolidin-l -yl)(( lR,3aS,5aR,5bR,7aR,9S, 11 aR, 1 IbR, 13aR, 13bR)-9-hydroxy- 5a,5b,8,8,l la-pentamethyl-l-(prop-l-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysen-3a- yl)methanone (step 5, 0.300 g, 0.43 mmol, 1.0 eq) and 2,2-dimethyl succinicanhydride (0.22 g, 1.75 mmol, 4.0 eq) in toluene (7.5 mL) was added DMAP (0.10 g, 0.87 mmol, 2.0 eq). The reaction mixture was heated at 90¡ãC for overnight. TLC indicated starting material was consumed and the desired product was observed. The mixture was concentrated under reduced pressure, cooled to 0¡ãC, acidified to pH= 5 with IN HC1 and extracted with CH2CI2. The combined organic extracts were washed with water, dried over Na2S04, filtered and evaporated under reduced pressure. The crude residue was purified by column chromatography by using 2percent methanol: dichloromethane as an eluent to gave the desired product (0.150 g, 43.0percent) as a white solid. H1 NMR (DMSO-d6, 300 MHz): delta 12.16 (s, 1H), 11.67 (s, 1H), 7.74 (d, 2H), 7.48 (s. 1H), 7.36 (d, 2H), 5.04 (s, 1H), 4.54 (d, 2H), 4.36 (t, 1H), 3.78 (s, 1H), 3.56 (bs, 2H), 2.08 (m 1H), 2.38-1.85 (m, 9H), 1.58-1.32 (m, 15H), 1.16 (m, 7H), 0.93-0.87 (m, 10H) and 0.83-0.78 (m, 12H); Mass: [M]+ 814.53 (100percent); HPLC: 89.00percent., 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; HETERO RESEARCH FOUNDATION; PANDURANGA REDDY, Adulla; PARTHASARADHI REDDY, Bandi; RATHNAKAR REDDY, Kura; VL SUBRAHMANYAM, Lanka; DAVID KRUPADANAM, Gazula, Levi; VENKATI, Mukkera; SUDHAKAR, Neela; SRINIVAS REDDY, Kallem; WO2014/105926; (2014); 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 138 (0458) 5-(3-Phenoxypropyl)isoxazole-3-carboxylic acid (0.50 g, 2.0 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (0.33 g, 2.4 mmol), triethylamine (0.25 g, 2.4 mmol) and 1-hydroxybenzotriazole (0.03 g, 0.24 mmol) were added to chloroform (amylene addition product) (5 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.46 g, 2.4 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 0.51 g of N-(tetrahydrofuran-3-ylmethyl)-5-(3-phenoxypropyl)isoxazole -3-carboxamide (hereinafter, referred to as Compound of Present Invention (145)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)):1.64-1.70(1H, m), 2.04-2.12(1H, m), 2.18-2.22(2H, m), 2.52-2.62(1H, m), 3.03(2H, t), 3.43-3.47 (2H, m), 3.59(1H, dd), 3.76(1H, dd), 3.83-3.94(2H, m), 4.02(2H, t), 6.50(1H, s), 6.88-6.90(2H, m), 6.94-6.98(1H, m), 7.00(1H, s), 7.28-7.30(2H, m), 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; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (2015); 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

5- (3-chloro-5-fluorobenzyloxymethyl) isoxazole-3-carboxylic acid (1.04 g, 3.6 mmol), Tetrahydrofuran-3-ylmethylamine hydrochloride (0.75 g, 5.5 mmol), Triethylamine (0.76 mL, 5.5 mmol) And 1-hydroxybenzotriazole (0.05 g, 0.4 mmol) Was added to chloroform (amylene added product) (10 mL). To the mixture, 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.84 g, 4.4 mmol) was added at room temperature, After stirring overnight, And concentrated under reduced pressure. Dilute hydrochloric acid was added to the residue, And extracted three times with ethyl acetate.The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, 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- (3-chloro-5-fluorobenzyloxymethyl) isoxazole-3-carboxamide (Hereinafter referred to as the amide compound (268)) 0.40 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

219823-47-9, (R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(mixture of stereoisomers) (5-(4-fluoro-2-hydroxyphenyl)-9-{2-methyl-2-[3-(trifluoromethyl)phenyl]propanoyl}-1,3,9- triazaspiro[5.5]undecan-2-one (50.0 mg, 101 mihoI, Intermediate 16), (3R)-oxolan-3-yl 4- methylbenzene-1 -sulfonate (36.8 mg, 152 pmol) and potassium carbonate (56 mg, 0.405 mmol) were mixed in dimethylformamide (0.6 ml_) and heated to 100 13 for 5 hours. The reaction was cooled down to room temperature, filtered and purified by preperative HPLC (Method 1 1) to give the title compound 42.0 mg (74 % yield). LC-MS (Method 4): Rt = 1.15 min; MS (ESIpos): m/z = 564 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) d [ppm]: 0.429 (0.64), 0.984 (1.48), 1.306 (5.33), 1.470 (5.72), 1.938 (1.48), 2.152 (1.35), 2.173 (2.57), 2.187 (3.08), 2.206 (2.70), 2.221 (1.80), 2.331 (2.70), 2.518 (16.00), 2.522 (10.15), 2.673 (2.83), 2.729 (0.58), 2.888 (2.83), 3.142 (3.28), 3.172 (4.18), 3.207 (3.98), 3.316 (2.44), 3.343 (3.08), 3.497 (1.22), 3.737 (5.85), 3.761 (8.55), 3.813 (3.73), 3.828 (2.76), 4.033 (0.84), 5.028 (2.44), 6.359 (8.80), 6.485 (5.40), 6.498 (4.76), 6.758 (4.24), 6.867 (3.41), 6.873 (3.53), 6.895 (4.95), 6.901 (4.31), 6.919 (1.80), 7.176 (1.67), 7.279 (3.41), 7.379 (7.26), 7.396 (6.30), 7.583 (3.73), 7.595 (5.53), 7.613 (3.28).

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; BAYER AKTIENGESELLSCHAFT; GRAHAM, Keith; AIGUABELLA FONT, Nuria; HEINRICH, Tobias; BRAeUER, Nico; LANGE, Martin; BADER, Benjamin; PRECHTL, Stefan; LIENAU, Philip; NOWAK-REPPEL, Katrin; POTZE, Lisette; STEUBER, Holger; NIU, Haitao; WANG, Qiuwen; (248 pag.)WO2020/48827; (2020); 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, General procedure: To a solutionof the corresponding aldehyde (1.2 eq.; unless stated otherwise) in DMF (2 inL per 0.3 mmol of aldehyde; unless stated otherwise) was added the corresponding amine (2.5 eq.; unless stated otherwise) and the resulting solution was stirred at 25 C to form the corresponding inline. Then, the corresponding isocyano(tosyl)methyl)arene reagent (1 eq.; unless stated otherwise) and K2CO3 (1.5 eq.; unless stated otherwise*) were added and the reaction mixture was stirred at 25 C (unless stated otherwise). The reaction was stopped after the time indicated for each particular reaction. The reaction progress was monitored by TLC. (0083) A saturated aqueous solution of NH4CI (10 mL per 1 mmol of aldehyde) was added to the reaction mixture, which was then extracted with EtOAc (2 x 30 mL per 1 mmol of aldehyde). The combined organic extracts were washed with H2O (2 x 25 mL per 1 mmol of aldehyde), dried over MgSCC, filtered, and the solvent was evaporated in vacuo to provide the crude product. The residue obtained after the workup was purified using column chromatography or preparative TLC (unless stated otherwise). (0084) * note: in cases when the amine was used as HC1 salt, 4 eq. of K2CO3 were used

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

Reference£º
Patent; MASARYKOVA UNIVERZITA; BRYJA, Vitezslav; JANOVSKA, Pavlina; GREGOROVA, Michaela; NEMEC, Vaclav; KHIRSARIYA, Prashant; PARUCH, Kamil; (171 pag.)WO2019/185631; (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.165253-29-2,3-(Bromomethyl)tetrahydrofuran,as a common compound, the synthetic route is as follows.

A solution of 3-(bromomethyl)tetrahydrofuran (8.OOg, 48.48 mmol) and 2-amino pyridine (9.12g,97.02 mmol) in sulfolane (250 mL) was heated to 80 00 for 70 hours. The reaction was thencooled to room temperature and then diluted with 5 L of CH2CI2, and twice extracted with 500 mL of water. The aqueous phase was concentrated in vacuo. To the residue was then added CH2CI2 (100 mL) and a thick orange oil precipitated. The CH2CI2 was decanted and the oil dried in vacuo to afford the desired salt as a wax contaminated with a trace amount of sulfolane (1 .1 g,9percent yield).LC-MS: mass calc?d. for 010H15N20 [M] 179.1, found 179.3; RT = 0.326 mm.

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

Reference£º
Patent; BASF SE; BANDUR, Nina Gertrud; MCLAUGHLIN, Martin John; POHLMAN, Matthias; DIETZ, Jochen; VON DEYN, Wolfgang; WO2015/28630; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem