Month: August 2020

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-fluoro-4-methoxybenzyloxymethyl) isoxazole-3-carboxylic acid (1.10 g, 3.9 mmol), Tetrahydrofuran-3-ylmethylamine hydrochloride (0.81 g, 5.9 mmol), Triethylamine (0.82 mL, 5.9 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 (0.90 g, 4.7 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, The following equation Indicated by N- (tetrahydrofuran-3-ylmethyl) -5- (3-fluoro-4-methoxyxybenzyloxymethyl) isoxazole-3-carboxamide (Hereinafter referred to as present amide compound (277)) 0.38 g was obtained.

184950-35-4 (Tetrahydrofuran-3-yl)methanamine hydrochloride 17750392, aTetrahydrofurans compound, is more and more widely used in various.

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.165253-31-6,(Tetrahydrofuran-3-yl)methanamine,as a common compound, the synthetic route is as follows.

A 0.5-2 mL microwave vial containing a stir bar was placed under argon by attaching a rubber septum and performing 4 vacuum/argon cycles. The intermediate from Example 9 Step C (100 mg, 0.146 mmol), sodium tert-butoxide (20.99 mg, 0.218 mmol), 2-(di- tert-butylphosphino)biphenyl (8.7 mg, 0.029 mmol), Pd2(dba)3 (13.33 mg, 0.015 mmol) were added, and the vial was sealed. While adding the solids to the vial, 30 mL of toluene was deoxygenated by bubbling argon through for 30 minutes; 1.0 mL of this was added to the sealed reaction vial. 3-(Aminomethyl)tetrahydrofuran (0.024 ml, 0.204 mmol) was added via microsyringe, and men argon was flushed gently through the vial for 5 min. The reaction was heated to 90C for 15 hours and then cooled to room temperature. A solution of tetrabutylammonium fluoride (1 M in tetrahydrofuran, 0.710 ml, 0.710 mmol) was added, and the vial was heated in a microwave oven for 10 min at 1500C. After cooling to room, temperature, the reaction mixture was partitioned between a 1 :1 mixture of EtOAc: ether (20 mL) and water (10 mL). The layers were separated, and the organic layer was washed sequentially with water (10 mL), saturated NaHCtheta3 (10 mL), and brine (10 mL), dried over Na2SO4, filtered, and concentrated. The resulting solid was purified by reverse phase HPLC. After lypophilization, the title compound was obtained. 1H NMR (600 MHz, DMSO) delta: 11.44 (s, 1 H), 9.57 (s, 1 H), 8.22 (m, 1 H), 7.68 (m, 1 H), 7.49 (t, 1 H, J= 6.3 Hz), 7.38 (t, 2 H, J= 8.2 Hz), 7.16 (d, 2 H, J= 5.6 Hz), 3.78 (m, 2 H), 3.64 (q, 1 H, J= 7.6 Hz), 3.51 (dd, 1 H, J= 8.5, 5.6 Hz), 3.17 (m, 2 H), 2.60 (m, 1 H), 2.04 (m, 1 H), 1.66 (m, 1 H): [M+l]+ 447.

165253-31-6 (Tetrahydrofuran-3-yl)methanamine 10898660, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; MERCK & CO., INC.; WO2007/145957; (2007); 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 139 (0459) 5-(4-Phenoxybutyl)isoxazole-3-carboxylic acid (0.52 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 (0.46g, 2. 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-(4-phenoxybutyl)isoxazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (146)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)):1.66-1.69(1H, m), 1.83-1.98(4H, m), 2.08-2.11(1H, m), 2.54-2.61(1H, m), 2.89(2H, t), 3.44-3.47(2H, m), 3.59(1H, dd), 3.77(1H, dd), 3.84-3. 94 (2H, m), 3.99(2H, t), 6.48(1H, s), 6.89(2H, ddd), 6.95(2H, dq), 7.27-7.31(2H, m)

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

1679-47-6, 3-Methyldihydrofuran-2(3H)-one is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A: ethyl 4-bromo-2-methylbutanoateTo a HBr saturated solution of EtOH (100 mL) at 0 C was added a-methyl~y- butyrolactone (3.0 mL, 31.7 mmol). The mixture was allowed to stir at rt for 3 days and then poured onto ice (500 g). After warming to rt, the mixture was extracted with Et20 (2×200 mL). The combined organic layer was further washed with H20 (300 mL) sat. NaHC03 (3×300 mL) and brine (300 mL), dried over MgSC>4, and concentrated to give the title compound, which was used without further purification: 1H NMR (500 MHz, CDC13) delta 4.15 (q, J= 7.1 Hz, 2H), 3.43 (dt, J= 1.1, 6.9 Hz, 2H), 2.68 (m, 1H), 2.26 (m, 2H)5 1.93 (m, 2H), 1.26 (t, J= 7.0 Hz, 3H), 1.19 (d, J= 7.1 Hz, 3H).

The synthetic route of 1679-47-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; NARGUND, Ravi; LO, Michael Man-Chu; YAN, Lin; HUO, Pei; FRANKLIN, Christopher; WO2011/53519; (2011); 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.112372-15-3,Furo[2,3-c]pyridine-2-carboxylic acid,as a common compound, the synthetic route is as follows.

e. methyl 3-(4-((furo[2.,3-clpyridine-2- carboxamido)methyl)phenylsulfonyl)propanoate:A 25-mL RBF equipped with a magnetic stir bar was charged with furo[2,3- c]pyridine-2-carboxylic acid (135 mg, 0.828 mmol), methyl 3-(4- (aminomethyl)phenylsulfonyl)propanoate hydrochloride (243 mg, 0.828 mmol), EtOH (Volume: 2.7 ml), N-METHYLMORPHOLINE (0.218 ml, 1.986 mmol), and finally EDC (190 mg, 0.993 mmol). The reaction mixture was stirred at rt. LCMS after 75 min shows some conversion, with longer-retaining by-product also forming. LCMS after 3 h shows some more conversion, but not significant. After 3.5 h, HOBT (6.34 mg, 0.041 mmol) was added. LCMS, 75 min after HOBT addition, not much different. LCMS after overnight not much different. The reaction mixture was slowly diluted with water (8.1 mL). The resulting slurry was stirred at rt for 1 h, then filtered on a 30-mL, medium frit, glass Buchner funnel. The solid was washed with water and dried under suction and a positive pressure of nitrogen to yield methyl 3-(4-((furo[2,3-c]pyridine-2- carboxamido)methyl)phenylsulfonyl)propanoate (0.12 g, 0.298 mmol, 36.0 % yield) as a slightly off- white fluffy powder.1H NMR (400 MHz, DMSO-d6): delta 9.67 (t, J = 6.1 Hz, 1H), 9.05 (s, 1H), 8.47 (d, J = 5.2 Hz, 1H), 7.85 (d, J = 8.4 Hz, 2H), 7.82 (dd, J = 5.3, 1.1 Hz, 1H), 7.65 (d, J = 0.8 Hz, 1H), 7.60 (d, J = 8.4 Hz, 2H), 4.59 (d, J = 6.1 Hz, 2H), 3.53 (t, J = 7.2 Hz, 2H), 3.49 (s, 3H), 2.59 (t, J = 7.2 Hz, 2H) ppm.ESMS: 403.03 (M+l)

The synthetic route of 112372-15-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; FORMA THERAPEUTICS, INC.; GENENTECH, INC.; BAIR, Kenneth, W.; BAUMEISTER, Timm; BUCKMELTER, Alexandre, J.; CLODFELTER, Karl, H.; DRAGOVICH, Peter; GOSSELIN, Francis; HAN, Bingsong; LIN, Jian; REYNOLDS, Dominic J.; ROTH, Bruce; SMITH, Chase, C.; WANG, Zhongguo; YUEN, Po-Wai; ZHENG, Xiaozhang; WO2012/31197; (2012); A1;,
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

Under the protection of argon gas, the 6 – (4-hydroxy -1,2-dihydro-furo [3,2-f] quinoline-9-yloxy)-N-methyl-1-naphthalene carboxamide 1p (20 mg, 0 . 052mmol), (R)-tetrahydrofuran-3-yl tosylates 13a (under WO2007007886 relates to the method of preparing) (63 mg, 0 . 26mmol), cesium carbonate (127 mg, 0 . 39mmol) and 2 ml in dimethyl acetamide is put into the reaction bottle, for 60 C reaction under 30 minutes. Cooling, adding 2 ml water and 5 ml ethyl acetate, separating, the aqueous phase is extracted with ethyl acetate (3 ml ¡Á 2), combined with the phase, saturated sodium chloride solution used for washing, drying by anhydrous magnesium sulphate, filtered, filtrate concentrated under reduced pressure, in order to thin-layer chromatography for purification of the resulting product A developing agent system, to obtain the title product (S) – 6 – ((4 – ((tetrahydrofuran-3-yl) oxy) – 1,2-dihydro-furo [3,2-f] quinolin-9-yl) oxy)-N-methyl-1-naphthalene carboxamide 13 (40 mg, pale yellow solid), yield: 67.0%.

As the paragraph descriping shows that 219823-47-9 is playing an increasingly important role.

Reference£º
Patent; Shanghai Hengrui Pharmaceutical Co., Ltd.; Jiangsu Hengrui Pharmaceutical Co., Ltd.; Lv Hejun; Chen Yiqian; Wang Shenglan; Hu Qiyue; Zheng Suxin; (73 pag.)CN103382206; (2016); B;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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

A solution of 50 gm of (S)-4-bromo-l-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)- benzene in tetrahydrofuran 300 mL and toluene 100 mL was cooled to -90 C to -100 C, 90 mL of n-hexyl Lithium (33% in tetrahydrofuran) was gradually added and the solution was stirred for 15 to 30 min. Then a solution of 2, 3, 4, 6 -tetrakis-0-(trimethylsilyl)-D- glucopyranone in toluene was added at -90 C to -100 C and the reaction mixture was stirred for 2 to 5 hrs. Thereafter 200 mL solution of methanesulphonic acid in methanol was added to the reaction mixture at -70 C to -90 C, the temperature of the reaction mixture was raised to 0 C to 15 C and the reaction mixture was stirred for 10 to 15 hrs at ambient temperature. The solution was then quenched with 8% aq. sodium bicarbonate solution followed by layer separation. The aqueous layer was extracted with ethylacetate (2 X 250 mL).The combined organic layer was washed with 250 mL 10% brine solution. The combined organic layer was concentrated under vacuum followed by stripping with acetonitrile 50mL to afford 95 gm of crude intermediate compound of formula (IV) as an oily mass. 200 mL of dichloromethane and 100 mL of acetonitrile was added to the oily mass at -30 C to -40 C followed by addition of trimethylsilane and borontrifluoride etherate. The reaction mixture was stirred for 2 to 3 hrs followed by addition of 550 mL of 8% aq. sodium bicarbonate solution at 5 C to 20 C. The organic layer was separated and extracted with dichloromethane (I X 250 mL and 1 X 100 mL). The combined organic layer was concentrated to get an oily mass of compound of formula (V). A solution of compound of formula (V) in 200 mL dichloromethane was added to slurry of 50 gm L-proline in 200 mL isopropanol and heated at 40 oC to 50 C for 7-10 hrs. The reaction mixture was filtered and washed with 25 mL dichloromethane and dried under vacuum to afford 53 gm of crystalline Form A of Empagliflozin L-proline complex.

The synthetic route of 915095-89-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; LUPIN LIMITED; AGARKAR, Amit, Madan; MITRA, Rangan; RANANAWARE, Umesh, Babanrao; GODBOLE, Himanshu, Madhav; SINGH, Girij, Pal; (27 pag.)WO2017/141202; (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.88675-24-5,Tetrahydrofuran-3-amine,as a common compound, the synthetic route is as follows.

EXAMPLE 1 7,8-Dimethoxy-N-(tetrahydrofuran-3-yl)quinazolin-4-amine To a solution of 4-chloro-7,8-dimethoxyquinazoline (1.5 g, 6.7 mmol) in DMF (30 mL) was added tetrahydrofuran-3-amine (698 mg, 8.01 mmol), DIPEA (2.3 mL, 13 mmol). Nitrogen was bubbled through the mixture for 5 min. The reaction was then heated at 100¡ã C. for 2 h. The crude mixture was evaporated and the residue was dissolved in ethyl acetate (20 mL), and filtered. The solid was washed with ethyl acetate (10 mL) to give 7,8-dimethoxy-N-(tetrahydrofuran-3-yl)quinazolin-4-amine 1.4 g (76percent).The racemate of 7,8-dimethoxy-N-(tetrahydrofuran-3-yl)quinazolin-4-amine 1.4 g was purified by SFC separation and numbered according to the order of elution: [0117] Stereoisomer 1 (first eluting by SFC): 388 mg, [0118] LC-MS (m/z) 276.1 (MH+) tR (minutes, method 3)=1.82. [0119] [alpha]20D=?32 (c=0.10 mg/mL, MeOH) [0120] Stereoisomer 2 (second eluting by SFC): 413 mg [0121] LC-MS (m/z) 276.1 (MH+) tR (minutes, method 3)=1.81. [0122] [alpha]20D=23 (c=0.10 mg/mL, MeOH)

#N/A

Reference£º
Patent; Kehler, Jan; Rasmussen, Lars Kyhn; Langgard, Morten; US2015/175584; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

112372-15-3, Furo[2,3-c]pyridine-2-carboxylic acid is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 4. A solution of furo[2,3-c]pyndine-2-carboxylic acid (120 mg, 0.74 mmol, 1.48 equiv), 4-(6-methyl-pyridine-3-suIfonyl)-benzyIamine ( 130 mg, 0.50 mmol, 1.00 equiv), EDCI (125 mg, 0.65 mmol, 1 .32 equiv), HOBt (90 mg, 0.67 mmol, 1.34 equiv), and diisopropylethylamine (0.5 mL) in DMF (5 mL) was stirred overnight at rt. After the reaction completed, the resulting solution was diluted with 100 mL of DCM. The mixture was washed with 2×30 mL of water and 2×30 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was then purified on a silica gel column eluted with DCM/MeOH (93 :7) to give 0.045 g (22%) of the title compound as a white solid. LC/MS (Method C, ESI), RT= 1 .70 min, m/z = 407.8 [M+H]+. 1G NMR (300 MHz, DMSO-d6) 6 9.60 (t, J = 6 0 Hz, 1 H), 9.05 (s, 1 H), 8.97 (d, J = 2.1 Hz, l H), 8.97 (d, J = 5.1 Hz, 1 H), 8.19 (dd, J = 8.1 Hz, J = 2.4 Hz, 1 H), 7.97 (d, J = 8.4 Hz, 2H), 7.81 (d, J = 4.8 Hz, 1 H), 7.64 (s, 1 H), 7.57 (d, J = 8.4 Hz, 2H), 7.47 (d, J = 8.4 Hz, 1 H), 4.55 (d, J = 6.0 Hz, 2H), 2.54 (s, 3H).

The synthetic route of 112372-15-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GENENTECH,INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; BUCKMELTER, Alexandre J.; CLODFELTER, Kanl H.; DRAGOVICH, Peter; HAN, Bingsong; LIN, Jian; LIU, Xiongcai; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; YUEN, Po-Wai; ZAK, Mark; ZHANG, Yamin; ZHENG, Xiaozhang; ZHAO, Guiling; WO2013/127268; (2013); 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.17347-61-4,2,2-Dimethylsuccinicanhydride,as a common compound, the synthetic route is as follows.

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%. 1H NMR (CDCl3, 400 MHz,ppm) delta: 4.76 (d, 1H, J=12 Hz, CH-OCO), in C3), 4.73 (s, 1H, C=CH,in C29), 4.60 (s, 1H, C=CH, in C29), 4.51-4.67 (m, 1H, CH-F, in C2),3.66 (s, 3H, CO2CH3), 2.92-2.98 (m, 1H, in C19), 2.62-2.76 (2d,J=16 Hz, CO-CH2-C(CH3)2), 2.17-2.23 (m, 3H, in C18 and C22),1.87-1.90 (m, 2H, in C1), 1.67 (s, 3H, CH3, in C30), 1.32 (s, 6H, 2CH3,CO2H-C(CH3)2-CH2-), 0.90 (s, 3H, CH3), 0.88 (s, 3H, CH3), 0.86 (s, 3H,CH3), 0.83 (s, 3H, CH3), 0.81 (s, 3H, CH3). 13C NMR (150 MHz, CDCl3) delta 176.50 (s), 176.23 (s), 170.83 (s), 150.27 (s), 109.60 (s), 89.47 (d,J=173.2 Hz), 81.47 (d, J=15.1 Hz), 56.38 (s), 54.89 (s), 51.13 (s),50.28 (s), 49.28 (s), 46.85 (s), 44.40 (d, J=17.8 Hz), 42.32 (s), 40.60(s), 39.42 (d, J=6.9 Hz), 38.55 (d, J=10.2 Hz), 38.01 (s), 36.80 (s),33.89 (s), 31.98 (s), 30.42 (s), 29.47 (s), 28.13 (s), 25.33 (s), 25.26 (s),25.16 (s), 24.92 (s), 20.93 (s), 19.17 (s), 18.02 (s), 17.39 (s), 17.14 (s),15.81 (s), 14.51 (s). 19F NMR (CDCl3, 376 MHz, ppm) delta: -190.57. ESIHRMS(m/z): calcd for C37H57FO6 [M+H]+: 617.4217, found617.4169.

As the paragraph descriping shows that 17347-61-4 is playing an increasingly important role.

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