Heterocyclic Building Blocks-Tetrahydrofuran

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.

5- (5-phenoxypentyl) isoxazole-3-carboxylic acid (0.70 g, 2.5 mmol), Tetrahydrofuran-3-ylmethylamine hydrochloride (0.42 g, 3.0 mmol), Triethylamine (0.31 g, 3.0 mmol) And 1-hydroxybenzotriazole (0.04 g, 0.30 mmol) Was added to chloroform (amylene added product) (8 mL). To the mixture, 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.58 g, 2.4 mmol) was added at room temperature, After stirring overnight, And concentrated under reduced pressure. Dilute hydrochloric acid was added to the concentrate, Extracted twice with ethyl acetate. The organic layer was 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- (5-phenoxypentyl) isoxazole-3-carboxamide (Hereinafter referred to as the amide compound (147)) 0.81 g was obtained., 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; SUMITA, YUSUKE; (264 pag.)JP2015/51963; (2015); 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.184950-35-4,(Tetrahydrofuran-3-yl)methanamine hydrochloride,as a common compound, the synthetic route is as follows.

Production Example 243 (0564) 5-[3-(4-Chlorophenyl)propyl]isoxazole-3-carboxylic acid (0.78 g, 2.9 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (0.60 g, 4.4 mmol), triethylamine (0.44 g, 4.4 mmol) and 1-hydroxybenzotriazole (0.04 g, 0.3 mmol) were added to a mixed solvent of chloroform (amylene addition product) (4 mL) and tetrahydrofuran (4 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.67 g, 3.5 mmol) was added to the mixture at room temperature, and the mixture was stirred at room temperature overnight and then concentrated under reduced pressure. Dilute hydrochloric acid was added to the residue, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated saline water and dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 0.78 g of N-(tetrahydrofuran-3-ylmethyl)-5-[3-(4-chlorophenyl]propyl) isoxazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (252)) represented by the following formula. 1H-NMR (CDCl3, TMS, delta (ppm)) : 1.62-1.73 (1H, m), 1.99-2.15 (3H, m), 2.53-2.63 (1H, m), 2.66(2H, t), 2.80(2H, t), 3.46(2H, t), 3.59 (1H, dd), 3.73-3.80 (1H, m), 3.83-3.95(2H, m), 6.46 (1H, s), 6.92 (1H, br s), 7.11(2H, d), 7.27(2H, d)

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

138498-97-2, 2-(Tetrahydrofuran-3-yl)acetic acid is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 58N-(2,5-dichloro-3-(((S)-4-(cyclopentanecarbonyl)-3-methylpiperazin-1-yl)methyl)phenyl)-2- (tetrahydrofuran-3-yl)acetamide (E58)H(YNNYpTo a suspension of 2-(tetrahydrofuran-3-yl)acetic acid (39.4 mg) in DCM (10 mL), oxalyl chloride (0.030 mL) was added dropwise. The reaction mixture was stirred at 40C for 30 mm. Solvent wasremoved by rotavap, then re-dissolved with DCM (1 mE), added to a solution of (S)-(4-(3 -amino2,5-dichlorobenzyl)-2-methylpiperazin-1 -yl)(cyclopentyl)methanone (D158, 70 mg) in pyridine (2 mL). The reaction mixture was stirred at RT overnight. The reaction mixture was diluted with DCM (10 mL) then washed with brine (10 mE). DCM layer was separated and concentrated. The residue was purified by MADP to afford the title compound (7 mg) as white solid. 111 NMR (400 MHz, MeOD-d4): 7.71 (d, J= 1.5 Hz, 1H), 7.35 (d, J= 2.0 Hz, 1H), 4.61 (brs, 0.5H), 4.33-4.17 (m, 1H), 3.90-3.51 (m, 5.5H), 3.45-3.27 (m, 1.5H), 3.01-2.67 (m, 3.5H), 2.67-2.41 (m, 3.5H), 2.27 (brs, 1H), 2.14-1.99 (m, 1.5H), 1.84-1.43 (m, 1011), 1.35-1.13 (m, 3H). MS (ESI): C24H33C12N303requires 481; found 482 {M+H].

138498-97-2, As the paragraph descriping shows that 138498-97-2 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; DENG, Jing; LEI, Hui; MA, Xin; LIN, Xichen; WO2015/180612; (2015); A1;,
Tetrahydrofuran – Wikipedia
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, Step B. Methyl 4- ( (3, 4-dimethoxybenzyl) amino) -2, 5-dihydrofuran-3-carboxylate (12)[0227][0228]To a solutio n of (3, 4-dimethoxyphenyl) methanamine (212 g, 1.27 mol) in anhydrous ethanol (1.1 L) was added dropwise the solution of crude 11 (300 g, assay 55 1.15 mol) in anhydrous ethanol (1.1 L) over 30 min using an addition funnel at 90 (note: slow addition is crucial to good yield) . The reaction was subsequently aged at 90 for 1 h. After the reaction was complete shown by LCMS, the reaction was cooled to ambient temperature and concentrated. The crude residual was purified by trituation with methanol (5 V) to give methyl 4- ( (3, 4-dimethoxybenzyl) amino) -2, 5-dihydrofuran-3-carboxylate (12) as a solid.1H NMR (CDCl3, 400 MHz) delta: 7.08 (m, 1H) , 6.46 (m, 2H) , 4.76 (m, 4H) , 4.19 (m, 2H) , 3.81 (s, 3H) , 3.81 (s, 3H) , 3.69 (s, 3H) , 2.69 (t, 1H) . LC/MS (m/z) : 294 (M+H)+.

The synthetic route of 57595-23-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; CAI, Jiaqiang; CRESPO, Alejandro; DEBENHAM, John; DU, Xiaoxing; LIU, Ping; LIU, Rongqiang; MADSEN-DUGGAN, Cristina B.; QUAN, Weiguo; SINZ, Christopher; WANG, Liping; (38 pag.)WO2016/45126; (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.184950-35-4,(Tetrahydrofuran-3-yl)methanamine hydrochloride,as a common compound, the synthetic route is as follows.

Tetrahydrofuran-3-ylmethylamine hydrochloride (0.17 g, 1.22 mmol) And triethylamine (0.12 g, 1.22 mmol) Was added to chloroform (amylene added product) (6 mL). To the mixture, 5- (3-phenoxybenzyl) isoxazole-3-carboxylic acid (0.30 g, 1.02 mmol) at room temperature, 1-Hydroxybenzotriazole (0.01 g, 0.10 mmol) And 1-ethyl-3- (3-dimethylaminopropyl) Carbodiimide hydrochloride (0.23 g, 1.22 mmol) was added, After stirring overnight, Dilute hydrochloric acid was added, It was extracted twice with chloroform. The organic layer was washed with saturated sodium bicarbonate water, After drying with anhydrous sodium sulfate, And concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, The following equation Indicated by N- (tetrahydrofuran-3-ylmethyl) -5- (3-phenoxybenzyl) isoxazole-3-carboxamide (Hereinafter referred to as present amide compound (163)) 0.31 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

13031-04-4, 4,4-Dimethyldihydrofuran-2,3-dione is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Examples 1-4 [00041] The process of the present invention as set forth in FIG. 1 is typically initiated by dissolving the alpha ketocarbonyl compound and the modifier in vessel (1). The resulting solution contains from about 0.1 wt % to about 100 wt % of the alpha ketocarbonyl compound and from about 1¡Á10-5 wt % to about 0.5 wt % of modifier. [00042] The mass flow is started at the reaction temperature, for example, at 17 C. or 20 C. (Examples 1 and 2, respectively). The above solution containing an alpha ketocarbonyl compound and a modifier is pumped into the fixed bed reactor (2) and contacted with hydrogen to start the hydrogenation reaction. Before catalytic runs, the reactor is flushed with nitrogen. [00043] Subsequently, the content of vessel (1) is continuously pumped into the fixed bed reactor. The solution flow rate is preferably from about 0.1 to about 50 ml/minute, the preferred flow of the alpha ketocarbonyl compound is 2¡Á10-5-2¡Á10-2 mol/gcat/minute. More preferably, the solution flow rate is preferably from about 2.5 to about 10 ml/minute, and the flow of the alpha ketocarbonyl compound is from about 2¡Á10-4-3¡Á10-3 mol/gcat/minute. [00044] The modifier flow rate is preferably from about 2¡Á10-9 to about 2¡Á10-4 mol/gcat/minute, such as, for example, from about 2¡Á10-8 to about 7¡Á10-6 mol/gcat/minute. [00045] Hydrogen is continuously fed into the fixed bed reactor via flow line (3) containing a compressor (4) and a pressure control system (5). The inert gas, e.g. nitrogen, is fed into the reactor (2) via line (7). [00046] The hydrogen flow rate into the reactor is metered and monitored by a rotameter. Suitable hydrogen flow rates are from about 0.0001 mol/minute (2.4 ml/minute) to about 1 mol/minute (24000 ml/minute), for example, from about 5¡Á10-6 to about 10 mol/gcat/minute. [00047] The hydrogenation reaction can be carried out at a relatively low temperature ranging between about -20 C. and about 100 C., the preferred temperature range is from about -10 C. to about 50 C., such as for example from about 0 C. to about 20 C. [00048] The pressure in the reactor is suitably adjusted to between about 2 bar and about 150 bar, preferably from about 40 bar to about 100 bar. [00049] The effluent from the hydrogenation reaction zone is fed over a two-step expansion module (6) to a separator where the alpha hydroxy carbonyl compound is recovered. [00050] The process set forth in FIG. 2 is initiated by dissolving the alpha ketocarbonyl compound and the modifier in vessel (1) or by adding a solution containing the modifier to a liquid alpha ketocarbonyl compound. The resulting solution has the following concentration: [00051] about 0.1 wt % to about 100 wt % of alpha ketocarbonyl compound; and [00052] about 1¡Á10-6 wt % to about 0.5 wt % of modifier. [00053] The reactor vessel (2) is charged with a supercritical solvent via flow line (3) containing a compressor (4) and a pressure control system (5). [00054] The organic flow is started at a reaction temperature of, for example, about 50 C. (Example 3) or 36 C. (Example 4). The solution set forth above is pumped into the fixed bed reactor (2) and contacted with hydrogen to start the hydrogenation reaction. [00055] Subsequently, the content of vessel (1) is continuously pumped into the fixed bed reactor with the same solution flow rate as in the process according to FIG. 1. [00056] The flow rate of the supercritical co-solvent is preferably from about 50 ml/minute to about 5000 ml/minute. [00057] When using a liquid alpha ketocarbonyl compound, the supercritical co-solvent is used with a flow rate of about 50 ml/minute to about 5000 ml/minute. [00058] The modifier flow rate is preferably from about 2¡Á10-11 to about 2¡Á10-4 mol/gcat/min. [00059] Hydrogen is continuously fed into the fixed bed reactor via flow line (7) containing a pressure control system (5). The hydrogen flow rate into the reactor was metered and monitored by a rotameter. [00060] Suitable hydrogen flow rates are from about 0.0001 mol/minute (2.4 ml/minute) to about 1 mol/minute (24000 ml/minute) such as for example from 5¡Á10-6 to about 10 mol/gcat/minute. [00061] The hydrogenation reaction can be carried out at a relatively low temperature ranging between about 20 C. to about 100 C., preferably from about 30 C. to about 60 C., such as for example from about 35 C. to about 50 C. The pressure is suitably adjusted to between about 2 bar to about 150 bar, preferably about 40 bar to about 100 bar., 13031-04-4

As the paragraph descriping shows that 13031-04-4 is playing an increasingly important role.

Reference£º
Patent; Roche Vitamins Inc.; US6646135; (2003); B1;,
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.

Description 20 : Dihydro-3(2H)-furanone; A mixture of 3-hydroxytetrahydrofuran (3.0 g, 0.034 mol) and pyridinium chlorochromate (14.7 g, 0.068 mol) in DCM (100 ml) was stirred at room temperature overnight. The title product was obtained by pouring the crude product through a silica pad using ethyl acetate as the eluent. The title product was obtained from 2 elutions (2.29 g; 79percent). 1H NMR (CDCI3) delta: 2.50 (2H, t), 3.87 (2H, s), 4.26 (2H, t).

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

Reference£º
Patent; GLAXO GROUP LIMITED; WO2006/67430; (2006); 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.204512-95-8,(S)-Tetrahydrofuran-3-amine hydrochloride,as a common compound, the synthetic route is as follows.

Example 96 N-[4-(dimethylphosphoryl)phenyl]-N?-(tetrahydrofuran-2-yl)-1,3,5-triazine-2,4-diamine (0697) (0698) To a solution of 4-chloro-N-[4-(dimethylphosphoryl)phenyl]-1,3,5-triazin-2-amine (prepared as in Example 92: 0.12 mmol) in 2 mL of ethanol is added 50 muL of triethylamine and (s)-3-aminotetrahydrofuran hydrochloride salt (14 mg, 0.12 mmol). The mixture can be microwaved at 120 degrees until formation of the desired compound. The reaction mixture is filtered through a syringe filter and purified by prep-HPLC., 204512-95-8

As the paragraph descriping shows that 204512-95-8 is playing an increasingly important role.

Reference£º
Patent; ARIAD PHARMACEUTICALS, INC.; Wang, Yihan; Huang, Wei-Sheng; Liu, Shuangying; Shakespeare, William C.; Thomas, Ranny M.; Qi, Jiwei; Li, Feng; Zhu, Xiaotian; Kohlmann, Anna; Dalgarno, David C.; Romero, Jan Antoinette C.; Zou, Dong; US2015/225436; (2015); 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.124391-75-9,(S)-(Tetrahydrofuran-3-yl)methanol,as a common compound, the synthetic route is as follows.

A solution of tetrahydro-3-furanmethanol (0.14 ml_, 1 .42 mmol), triethylamine (0.2 ml_, 1 .42 mmol) in THF (4 ml.) was prepared in a round bottom flask under inert atmosphere. The mixture was cooled to 0C and freshly prepared oleoyl chloride (212 mg, 0.7 mmol) in THF (4 ml.) was added via cannula. After stirring for overnight at RT, the mixture was worked up by addition of distilled water (6 ml_). The product was extracted with ethyl acetate (3 x 15 ml_), dried over MgS04 and purified by column chromatography on Si02. (petroleum ether/ ethyl acetate (5:1 ), Rf = 0.70), m= 236.1 mg. Aspect: colorless oil. yield: 93 %. 1H NMR (500 MHz, CDCI3) d (ppm): 5.34 (qd, 2H, J = 1.9 Hz, J = 3.9 Hz), 4.09 (dd, 1 H, J = 6.5 Hz, J = 10.9 Hz), 3.97 (dd, 1 H, J = 8.0 Hz, J = 10.9 Hz), 3.90-3.82 (m, 2H), 3.79-3.71 (m, 1 H), 3.56 (dd, 1 H, J = 5.6 Hz, J = 8.8 Hz), 2.62-2.51 (m, 1 H), 2.30 (t, 2H, J = 7.5 Hz), 2.08-1.96 (m, 5H), 1 .67-1 .57 (m, 4H), 1 .37-1.20 (m, 19H), 0.88 (t, 3H, J = 6.9 Hz). 13C {1 H} NMR (126 MHz, CDCI3) d (ppm): 173.77, 130.00, 129.71 , 70.54, 67.70, 65.66, 38.26, 34.25, 31.89, 29.75, 29.67, 29.50, 29.30 (2x), 29.14, 29.10, 29.08, 28.94, 27.20, 27.14, 24.95, 22.66, 14.09., 124391-75-9

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

Reference£º
Patent; UNIVERSITE DE BOURGOGNE; INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE); KHAN, Naim; JUGE, Sylvain; HICHAMI, Aziz; BAYARDON, Jerome; MANGIN, Floriane; KHAN, Amira; (0 pag.)WO2019/228994; (2019); 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 155 (0475) Tetrahydrofuran-3-ylmethylamine hydrochloride (0.17 g, 1.22 mmol) and triethylamine (0.12 g, 1.22 mmol) were added to chloroform (amylene addition product) (6 mL). 5-(3-Phenoxybenzyl)isoxazole-3-carboxylic acid (0.30 g, 1.02 mmol), 1-hydroxybenzotriazole (0.01 g, 0.10 mmol) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.23g, 1.22 mmol) were added to the mixture at room temperature, and the mixture was stirred overnight. Then, dilute hydrochloric acid was added thereto, and the mixture was extracted twice with chloroform. The organic layer was washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 0.31 g of N-(tetrahydrofuran-3-ylmethyl)-5-(3-phenoxybenzyl)isoxazole -3-carboxamide (hereinafter, referred to as Compound of Present Invention (163)) represented by the following formula. 1H-NMR ( CDCl3, TMS, delta(ppm)):1.62-1.71(1H, m), 2.03-2.11(1H, m), 2.51-2.61(1H, m), 3.43-3.46(2H, m), 3.56-3.59(1H, m), 3.73-3.79(1H, m), 3.82-3.94(2H, m), 4.08(2H, s), 6.41(1H, s), 6.90-7.02(6H, m), 7.10-7.14(1H, m), 7.28-7.37(3H, m), 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