New learning discoveries about 57319-65-0

57319-65-0 6-Aminoisobenzofuran-1(3H)-one 93631, abenzofuran compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.57319-65-0,6-Aminoisobenzofuran-1(3H)-one,as a common compound, the synthetic route is as follows.

57319-65-0, Phthalide 29. To a stirred solution of 6-aminophthalide (10.0 g, 67.0 mmol, 1.0 equiv), DMAP (164 mg, 1.34 mmol, 0.02 equiv), and Et3N (13.6 g, 18.7 mL, 134 mmol, 2.0 equiv) in THF (40 mL) at 0 C, Boc20 (17.6 g, 80.4 mmol, 1.2 equiv) was added portionwise over 10 min under vigorous stirring at 0 C (CA UTION: gas evolution). Upon completion of addition, the ice bath was removed and the reaction mixture was stirred for 3 h at 40 C and was diluted with EtOAc (50 mL), cooled to 0 C, quenched by careful addition of saturated aq. NH4CI (40 mL). The resulting mixture was extracted with EtOAc (3 x 50 mL), and the combined organic layers were washed with water (50 mL) and brine (50 mL), dried over MgSC>4 and concentrated. Flash column chromatography (silica gel, hexanes:EtOAc 2: 1 to 1 : 1) gave phthalide 29 as a yellowish solid (13.4 g, 53.6 mmol, 80% yield). 29: R/ = 0.31 (silica gel, hexanes:EtOAc 2: 1); IR (film) vmax = 3341, 2979, 2931, 2851, 1741, 1719, 1604, 1538, 1497, 1450, 1423, 1390, 1365, 1316, 1299, 1234, 1126, 1063, 1002 cm”1; FontWeight=”Bold” FontSize=”10″ H NMR (500 MHz, CDC13): delta = 7.83 (d, J = 2.0, 1 H), 7.76 (d, J = 7.8, 1 H), 7.36 (d, J = 8.3, 1 H), 6.92 (br, 1 H), 5.23 (s, 2 H), 1.47 (s, 9 H) ppm; 1 C NMR (125 MHz, CDC13): delta = 170.9, 152.5, 140.5, 139.6, 126.4, 124.8, 122.5, 114.6, 81.1, 69.5, 28.2 ppm; HRMS (ESI-TOF): calcd for Ci3H16N04+ [M+H+]: 250.1074, found 250.1076.

57319-65-0 6-Aminoisobenzofuran-1(3H)-one 93631, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; WILLIAM MARSH RICE UNIVERSITY; BRISTOL-MYERS SQUIBB COMPANY; THE SCRIPPS RESEARCH INSTITUTE; NICOLAOU, Kyriacos, C.; LU, Min; MANDAL, Debashis; GANGWAR, Sanjeev; CHOWDARI, Naidu, S.; POUDEL, Yam, B.; WO2015/23879; (2015); A1;,
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Analyzing the synthesis route of 57319-65-0

As the paragraph descriping shows that 57319-65-0 is playing an increasingly important role.

57319-65-0,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.57319-65-0,6-Aminoisobenzofuran-1(3H)-one,as a common compound, the synthetic route is as follows.

To a solution of 6-aminoisobenzofuran-1(3H)-one 1 (1 g, 6.70 mmol) in methanol (1 mL) was added ethane-1,2-diamine (2.246 mL, 33.5 mmol). The reaction mixture was stirred at RT for 3 h. LCMS (M+H-H2O=192.2) showed the disappearance of starting material and the presence of product. The solvent and the excess reagent was removed by evaporation and the crude 8 was taken to next step.

As the paragraph descriping shows that 57319-65-0 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; POUDEL, Yam B.; GANGWAR, Sanjeev; (37 pag.)US2019/365915; (2019); A1;,
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Benzofuran | C8H6O – PubChem

Some tips on 57319-65-0

The synthetic route of 57319-65-0 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.57319-65-0,6-Aminoisobenzofuran-1(3H)-one,as a common compound, the synthetic route is as follows.

57319-65-0, A solution of 400 mg (1.44 mM) of 4-chloro-6,7-diethoxy-quinoline-3-carbonitrile, 230 mg (1.54 mM) of 6-Aminophthalide and 161 mg of pyridine hydrochloride in 12 ml of 2-methoxyethanol was refluxed for 3 hours. To the warm solution was added 1 ml of 1M sodium carbonate and the sample was heated for 5 minutes at 100C, then poured into 300 ml of ice water. The solid was collected, washed with water followed by ether and dried under vacuum at 80C to yield 535 mg of 6,7-Diethoxy-4-(3-oxo-1,3-dihydro-isobenzofuran-5-ylamino)-quinoline-3-carbonitrile as a white solid: mass spectrum (electrospray, m/e): M+H 390.1, mp = 280-284C.

The synthetic route of 57319-65-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Wyeth Holdings Corporation; EP1117659; (2003); B1;,
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Benzofuran | C8H6O – PubChem

Downstream synthetic route of 57319-65-0

57319-65-0 6-Aminoisobenzofuran-1(3H)-one 93631, abenzofuran compound, is more and more widely used in various fields.

57319-65-0, 6-Aminoisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

57319-65-0, 2,2,2-trichloroethyl (3-oxo-1,3-dihydroisobenzofuran-5-yl)carbamate 2 To a suspension of 6-aminoisobenzofuran-1(3H)-one 1 (Maybridge, 13.43 g, 90 mmol) in dichloromethane (DCM, 200 mL) at 0 C. was added 2,2,2-trichloroethyl carbonochloridate 1a (18.23 mL, 135 mmol) and pyridine (17.79 mL, 180 mmol). The reaction mixture was stirred at room temperature (RT, ca. 25 C.) for 1 h. Thin layer chromatography (TLC) and high performance liquid chromatography (HPLC) showed the reaction was complete. The reaction mixture was filtered and washed with DCM (2*30 mL) to afford carbamate 2 as a white solid (17.03 g, 58%). LCMS: [M+l]=324.

57319-65-0 6-Aminoisobenzofuran-1(3H)-one 93631, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; CHOWDARI, Naidu S.; Gangwar, Sanjeev; Sufi, Bilal; US2013/209494; (2013); A1;,
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Simple exploration of 57319-65-0

The synthetic route of 57319-65-0 has been constantly updated, and we look forward to future research findings.

57319-65-0, 6-Aminoisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,57319-65-0

Example 16 3-(6-Amino-3H-isobenzofuran-1-ylidene)-5-chloro-1,3-dihydro-indol-2-one To a solution of 5-chlorooxindole (0.629 g, 3.78 mmol) in 10.0 mL monoglyme was added 7.51 mL sodium hexamethyldisilazane (1.0 M in THF) over 3 min. After stirring at room temperature for 8 min, a slurry of 6-aminophthalide (0.561 g, 3.78 mmol) in 4.0 mL of monoglyme was added in one portion. The mixture was stirred for 40 min and then quenched into 100 mL of 4% aqueous HCl solution. The yellow solid was filtered and then partitioned between EtOAc and saturated NaHCO3 (heated to dissolve the solid). The organic phase was washed with H2O, brine and then dried with Na2SO4. The solvent was removed in vacuo and the residue was triturated with MeOH to give the title compound (439 mg, 39%) as a yellow solid.

The synthetic route of 57319-65-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Allergan Sales, LLC; US6541504; (2003); B1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

Downstream synthetic route of 57319-65-0

As the paragraph descriping shows that 57319-65-0 is playing an increasingly important role.

57319-65-0, 6-Aminoisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

57319-65-0, 6-Amino-1(3H)-isobenzofuranone (3.0 g, 20 mmol) obtained from Example 26-(1) was dissolved in a mixture of 47% aqueous hydrobromic acid solution (15 ml) and water (15 ml), then the mixture was cooled to 0C, and a solution of sodium nitrite (1.45 g, 21 mmol) in water (7 ml) was slowly added thereto. Further, a solution of copper (I) bromide (3.6 g, 25 mmol) dissolved in 47% aqueous hydrobromic acid solution (10 ml) was added to the reaction mixture, and the resulting mixture was stirred at 80C for 20 minutes. After cooling the mixture, the liberated product was collected by filtration and then washed with water. The obtained pale brown solid was dissolved in ethyl acetate, then the insoluble material was removed by filtration, and the filtrate was washed successively with a 1N aqueous solution of hydrochloric acid, an aqueous solution of sodium hydrogen carbonate, and an aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated to afford the title compound (3.57 g, 84% yield) as a crystalline solid. NMR spectrum (400 MHz, CDCl3) delta ppm: 5.289 (2H, s), 7.391 (1H, d, J=8 Hz), 7.808 (1H, dd, J=8, 2 Hz), 8.068 (1H, d, J=2 Hz) IR spectrum nu max KBr cm-1: 1778, 1458, 1359, 1191, 1046, 998, 768 Mass spectrum m/z (EI): 214, 212 (M+), 185, 183, 157, 155.

As the paragraph descriping shows that 57319-65-0 is playing an increasingly important role.

Reference£º
Patent; Sankyo Company, Limited; EP1362856; (2003); A1;,
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Simple exploration of 57319-65-0

The synthetic route of 57319-65-0 has been constantly updated, and we look forward to future research findings.

57319-65-0,57319-65-0, 6-Aminoisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a cooled solution (0 C) of 6-aminophthalide (5.13 g, 34.05 mmol) in THF (80 ml.) was added /V-bromosuccinimide (6.12 g, 34.05 mmol, 1 eq). The cooling bath was removed and the solution stirred for 1 h, then the solvent was removed under reduced pressure. The yellow residue was taken up in ethyl acetate (400 ml) and washed three times with water (200 ml. each). The organic phase was dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to give 6-amino-7-bromophthalide as a brown solid (6.53 g, 28.63 mmol, 84%). Rf = 0.2 (cyclohexane/ethyl acetate 2:1 ); UPLC-MS: tR = 1.45 min (gradient 10-90% B in 5 min); UPLC-purity (210 nm) = 83.1%; ESI-MS: (calculated MH+: 227.97, 229.96, found: 228.01 , 230.01 )

The synthetic route of 57319-65-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BELYNTIC GMBH; ZITTERBART, Robert; REIMANN, Oliver; (102 pag.)WO2020/43747; (2020); A1;,
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Brief introduction of 57319-65-0

As the paragraph descriping shows that 57319-65-0 is playing an increasingly important role.

57319-65-0, 6-Aminoisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a stirred solution of 2-(3,4-bis(3,4-dimethoxyphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid 1 (70 mg, 0.16 mmol) and EDCI (47 mg, 0.25 mmol) in dry CH2Cl2 (5 mL) at 0 C under N2 atmosphere was added DMAP (30 mg, 0.25 mmol) and 14, 15, 18, or 19 (0.2 mmol) in batch over 10 min. The reaction mixture was stirred overnight while the reaction temperature rose to room temperature naturally. The solution was diluted with CH2Cl2 (20 mL), washed with brine, and dried over anhydrous MgSO4. The solvent was evaporated to dryness to give the crude residue. The residue was purified by flash chromatography on silica gel (EtOAc/PE = 2:1, v/v) to afford the desired compound 16, 17. 2-(3,4-Bis(3,4-dimethoxyphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-(3-oxo-1,3-dihydroisobenzofuran-4-yl)-acetamide (16) Yield 69%; mp 244-246 C; 1H NMR (CDCl3, 500 MHz) d: 8.4 (s,1H), 8.0 (d, J = 8.2 Hz, 1H), 7.94 (s, 1H), 7.42 (d, J = 8.3 Hz, 1H), 7.23 (d, J = 8.4 Hz, 2H), 7.06 (s, 3.70 (s, 6H); 13C NMR (CDCl3, 126 MHz) d: 170.7, 164.9, 150.5, 148.7, 142.1, 138.5, 134.5, 126.1, 123.6, 122.7, 121.0, 116.1, 112.5, 110.9, 69.7, 55.9, 55.8, 41.8, 29.6; HRMS calcd for (C30H26O9N2+H)+ 559.1711, found 559.1704., 57319-65-0

As the paragraph descriping shows that 57319-65-0 is playing an increasingly important role.

Reference£º
Article; Wang, Zhen; Wong, Iris L.K.; Li, Fu Xing; Yang, Chao; Liu, Zhen; Jiang, Tao; Jiang, Ting Fu; Chow, Larry M.C.; Wan, Sheng Biao; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5566 – 5573;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

Some tips on 57319-65-0

The synthetic route of 57319-65-0 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.57319-65-0,6-Aminoisobenzofuran-1(3H)-one,as a common compound, the synthetic route is as follows.

57319-65-0, To a suspension of 6-aminoisobenzofuran-1(3H)-one 4 (13.43 g, 90 mmol) in CH2Cl2 (200 mL) at 0 C was added 2,2,2-trichloroethyl carbonochloridate (18.23 mL, 135 mmol) followed by pyridine (17.79 mL, 180 mmol) and allowed to stir at room temperature for 1 h. TLC and HPLC shows reaction was complete. Filtered and washed with DCM (2×30 ml) to afford product 5 as white solid (17.03g, 58%). LCMS: [M+1] = 324. 1H NMR (400 MHz,Acetone-D6): delta 9.55 (brs, 1H), 8.16 (d, J = 2.0 Hz, 1H), 7.91 (dd, J = 8.0, 2.0 Hz, 1H), 7.64 (d, J = 8.0 Hz, 1H), 5.36 (s, 2H), 4.95 (s, 2H).

The synthetic route of 57319-65-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Chowdari, Naidu S.; Pan, Chin; Rao, Chetana; Langley, David R.; Sivaprakasam, Prasanna; Sufi, Bilal; Derwin, Daniel; Wang, Yichong; Kwok, Eilene; Passmore, David; Rangan, Vangipuram S.; Deshpande, Shrikant; Cardarelli, Pina; Vite, Gregory; Gangwar, Sanjeev; Bioorganic and Medicinal Chemistry Letters; vol. 29; 3; (2019); p. 466 – 470;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

Downstream synthetic route of 57319-65-0

57319-65-0 6-Aminoisobenzofuran-1(3H)-one 93631, abenzofuran compound, is more and more widely used in various fields.

57319-65-0, 6-Aminoisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

57319-65-0, A mixture of 6-aminoisobenzofuran-1(3H)-one 1 (1.0 g, 6.70 mmol) and methanamine (2M in MeOH, 16.76 mL, 33.5 mmol) in DCM (5 mL) was stirred for 3 days. LCMS (M+H-H2O=163.0) showed the presence of ring-opened product. The solvent was evaporated to obtain compound 2 as a colorless paste (quantitative yield).

57319-65-0 6-Aminoisobenzofuran-1(3H)-one 93631, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; POUDEL, Yam B.; GANGWAR, Sanjeev; (37 pag.)US2019/365915; (2019); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem