Heterocyclic Building Blocks-Tetrahydrofuran

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
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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