Simple exploration of 69999-16-2

As the paragraph descriping shows that 69999-16-2 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.69999-16-2,2,3-Dihydrobenzofuranyl-5-acetic acid,as a common compound, the synthetic route is as follows.,69999-16-2

Step 3. N-[2-(2, 3-dihydro-l-benzofiiotaran-5~ylmethyl)-l-(3-methylbutyl)-lH-benzimidazol-5-yl]~ N, 3-dimethylbutanamide[0171] To a mixture of N-{3-amino-4-[(3-methylbutyl)amino]phenyl}-N,3-dimethylbutanamide (Step 2 of Example 2, 0.097g, 0.33 mmol, lequiv), 2,3-dihydro-l-benzofuran-5-ylacetic acid (0.065g, 0.36 mmol, 1.1 equiv) and HATU (0.139g, 0.366 mmol, 1.1 equiv) was added a solution of DIPEA (116 muL, 0.666 mmol, 2equiv) in DMF (5 mL). The mixture was stirred overnight at room temperature. Complete consumption of the starting material was confirmed by LC-MS. DMF was removed under reduced pressure. Ethyl acetate was added to the resulting residue. The organic layer was washed once with a saturated aqueous NaHCO3 solution, once with brine and dried over anhydrous Na2SO4. Ethyl acetate was removed under reduce pressure. The resulting residue was dissolved in dichloroethane and a few drops of concentrated HCl were added. The mixture was stirred at 80 C for a few hours. Complete consumption of the starting material was confirmed by LC-MS. Dichloromethane was added. The organic layer was washed once with a 2M aqueous NaOH solution, once with brine and dried over anhydrous Na2SO4. Dichloromethane was removed under reduced pressure. The resulting residue was purified by reversed-phase HPLC and lyophilized to afford N-[2-(2,3-dihydro-l-benzofuran-5-yhnethyl)-l- (3-methylbutyl)-lH-benzimidazol-5-yl]-N,3-dimethylbutanamide as the corresponding TFA salt (0.110 mg) in 58% yield. 1H NMR (400 MHz, METHANOL-D4) delta ppm 0.72 – 0.89 (m, 6 H) 0.96 (d, /=6.64 Hz, 6 H) 1.47 – 1.54 (m, 2 H) 1.64 – 1.76 (m, 1 H) 1.91 – 2.14 (m, 3 H) 3.19 (t, /=8.69 Hz, 2 H) 4.36 – 4.43 (m, 2 H) 4.50 (s, 2 H) 4.55 (t, /=8.69 Hz, 2 H) 6.76 (d, /=8.20 Hz, 1 H) 7.08 (dd, /=8.30, 1.86 Hz, 1 H) 7.21 (s, 1 H) 7.46 (dd, /=8.79, 1.95 Hz, 1 H) 7.65 (d, /=1.37 Hz, 1 H) 7.85 (d, /=8.59 Hz, 1 H); MS (ESI) m/z 434.0 (M+H)+; Anal. Calcd (%) for C27H35N3O2 + 1.1 TFA + 0.1 H2O: C, 62.54; H3 6.52; N, 7.49. Found: C, 62.51; H, 6.59; N 7.46.

As the paragraph descriping shows that 69999-16-2 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; WO2007/91950; (2007); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

New learning discoveries about 69999-16-2

The synthetic route of 69999-16-2 has been constantly updated, and we look forward to future research findings.

69999-16-2, 2,3-Dihydrobenzofuranyl-5-acetic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,69999-16-2

(A) Preparation of 5-(2-hydroxyethyl)-2,3-dihydrobenzofuran STR76 A solution of (2,3-dihydrobenzofuran-5-yl)acetic acid (4.9 g — see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added over 10 minutes, dropwise, to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was then added dropwise with caution followed by 10% aqueous sodium hydroxide (1.5 ml) and, finally, water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate (2*50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as an oil, yield 3.3 g. 1 H N.M.R. (CDCl3) delta=7.10 (s, 1H); 7.00 (d, 1H); 6.75 (m, 1H); 4.65-4.55 (m, 2H); 3.90-3.75 (m, 2H); 3.30-3.15 (m, 2H); 2.90-2.80 (m, 2H); 1.85-1.75 (brs, 1H) ppm.

The synthetic route of 69999-16-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Pfizer Inc.; US5192765; (1993); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

Simple exploration of 69999-16-2

As the paragraph descriping shows that 69999-16-2 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.69999-16-2,2,3-Dihydrobenzofuranyl-5-acetic acid,as a common compound, the synthetic route is as follows.

EXAMPLE 6 Obtaining 2-(2,3-dihydrobenzofuran-5-yl)-acetamide [Show Image] 5 ml of DMF and a solution of 45 ml (0.617 moles) of thionyl chloride in 100 ml of acetonitrile were added consecutively to a solution of 100 g (0.560 moles) of (2,3-dihydrobenzofuran-5-yl)-acetic acid in 900 ml of acetonitrile. The reaction mixture was maintained at 45C for 4 hours. Once the reaction was finished, the obtained solution was cooled at 15C and was slowly added during approximately one hour to a mixture consisting of 800 ml of 25% NH3 aqueous solution and 400 ml of acetonitrile cooled at 5C. Once the reaction mixture was added, it was maintained at room temperature for 4 hours. Then 800 ml of water were added and it was stirred for 30 minutes; the obtained phases were separated and the aqueous phase was extracted with 2x 100 ml of acetonitrile. The combined extracts were concentrated under vacuum to a final volume of 500 ml. The obtained suspension was maintained under stirring at 5C for 30 minutes and the solid was isolated by filtration, obtaining 96.5 g (97% yield) of a white solid having the following spectroscopic properties: 1H NMR (400 MHz, DMSO): 3.09 (2H, t, J=8Hz), 3.26 (2H, s), 4.45 (2H, t, J=8Hz), 6.64 (1H, d, J=8Hz), 6.81 (1H, s), 6.93 (1H, d, J=8Hz), 7.09 (1H, s), 7.34 (1H, s) ppm. 13C NMR (100 MHz, DMSO): 29.12 (CH2), 41.69 (CH2), 70.79 (CH2), 108.39 (CH), 125.7 (CH), 127.09 (C), 128.21 (C), 128.33 (CH), 158.30 (C), 172.89 (C) ppm. LRMS (electrospray, positive ion): m/z [M++Na+] 199.8

As the paragraph descriping shows that 69999-16-2 is playing an increasingly important role.

Reference£º
Patent; Ragactives, S.L.; EP2236509; (2010); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

Some tips on 69999-16-2

As the paragraph descriping shows that 69999-16-2 is playing an increasingly important role.

69999-16-2, 2,3-Dihydrobenzofuranyl-5-acetic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

PREPARATION 30 5-(2-Hydroxyethyl)-2,3-dihydrobenzofuran STR136 A solution of (2,3-dihydrobenzofuran-5-yl)acetic acid (4.9 g–see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added dropwise over 10 minutes to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0 C. The mixture was allowed to warm to room temperature and stirred for 1 hour. Water (1.5 ml) was cautiously added dropwise followed by 10% aqueous sodium hydroxide (1.5 ml) and, finally, water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate (2*50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as as oil, (3.3 g). 1 H-n.m.r. (CDCl3) delta=7.10 (s, 1H); 7.00 (d, 1H); 6.75 (m, 1H); 4.65-4.55 (m, 2H); 3.90-3.75 (m, 2H); 3.30-3.15 (m, 2H); 2.90-2.80 (m, 2H); 1.85-1.75 (broad s, 1H) ppm.

As the paragraph descriping shows that 69999-16-2 is playing an increasingly important role.

Reference£º
Patent; Pfizer Inc.; US5089505; (1992); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

Simple exploration of 69999-16-2

As the paragraph descriping shows that 69999-16-2 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.69999-16-2,2,3-Dihydrobenzofuranyl-5-acetic acid,as a common compound, the synthetic route is as follows.

Preparation 16 Preparation of 5-(2-hydroxyethyl) -2,3-dihydrobenzofuran A solution of (2,3-dihydrobenzofuran-5-yl)acetic acid (4.9 g – see EP-A-132130) in anhydrous tetrahydrofuran (50 ml) was added dropwise over 10 minutes to a stirred suspension of lithium aluminium hydride (1.57 g) in anhydrous tetrahydrofuran (50 ml) at 0C. The mixture was allowed to warm to room temperature and stirred for 1 hour. water (1.5 ml) was cautiously added dropwise followed by 10% aqueous sodium hydroxide (1.5 ml) and, finally, water (4.5 ml). The mixture was filtered and the inorganic salts washed with ethyl acetate (2 x 50 ml). The filtrate and washings were combined and concentrated in vacuo to give the title compound as an oil, yield 3.3 g. 1H-N.M.R. (CDCl3 delta = 7.10 (s, 1H); 7.00 (d, 1H); 6.75 (m, 1H); 4.65-4.55 (m, 2H); 3.90-3.75 (m, 2H); 3.30-3.15 (m, 2H); 2.90-2.80 (m, 2H); 1.85-1.75 (brs, 1H) ppm.

As the paragraph descriping shows that 69999-16-2 is playing an increasingly important role.

Reference£º
Patent; Pfizer Limited; PFIZER INC.; EP505377; (1996); B1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

Simple exploration of 69999-16-2

As the paragraph descriping shows that 69999-16-2 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.69999-16-2,2,3-Dihydrobenzofuranyl-5-acetic acid,as a common compound, the synthetic route is as follows.

Step 3. 2~(2,3-dihydro-l~benzofuran-5-ylmethyl)-l-(3-rnethylbutyl)-N,N-bis(2,2,2-trifluoro- ethyI)-lH-benzimidazole-5-carboxamide[0168] To a mixture of 3-amino-4-[(3-methylbutyl)amino]-N,N-bis(2,2,2- trifluoroethyl)benzamide (Step 2 of the Example 1, 0.175g, 0.454 mmol, lequiv), 2,3-dihydro-l- benzofuran-5-ylacetic acid (0.089g, 0.50 mmol, 1.1 equiv) and HATU (0.19Og, 0.500 mmol, 1.1 equpsiloniv) was added a solution of DIPEA (160 muL, 0.92 mmol, 2equiv) in DMF (5 mL). The mixture was stirred overnight at room temperature. Complete consumption of the starting material was confirmed by LC-MS. DMF was removed under reduced pressure. Ethyl acetate was added to the resulting residue. The organic layer was washed once with a saturated aqueous <n=”54″/>NaHCtheta3 solution, once with brine and dried over anhydrous Na2SO4. Ethyl acetate was removed under reduce pressure. The resulting residue was dissolved in dichloroethane and a few drops of concentrated HCl were added. The mixture was stirred at 80 C for 3 hours. Complete consumption of the starting material was confirmed by LC-MS. Dichloromethane was added. The organic layer was washed once with a 2M aqueous NaOH solution, once with brine and dried over anhydrous Na2SO4. Dichloromethane was removed under reduced pressure. The resulting residue was purified by column chromatography on silica gel (hexanes/EtOAc, 50:50) to afford 2-(2,3-dmydro-l-benzofuran-5-ylmethyl)-l-(3-methylbutyl)-N,N-bis(2,2,2-trifluoro- ethyl)-lH-benzimidazole-5-carbochiamide (0.173 mg) in 72% yield. The product was dissolved in methanol (about 5 mL) and 1 equivalent of TFA was added. The mixture was stirred at room temperature for about 30 minutes. Methanol was removed under reduced pressure. Water was added and the resulting residue was lyophilized to afford 2-(2,3-dihydro-l-benzofuran-5- ymiethyl)-l-(3-me1hylbu1yl)-N,N-bis(2,2,2-trifluoro-e&yl)-lH-benzimidazole-5-carboxamide as the corresponding TFA salt. 1H NMR (400 MHz, METHANOL-D4) 6 ppm 0.96 (d, /=6.64 Hz, 6 H) 1.45 – 1.54 (m, 2 H) 1.63 – 1.75 (m, 1 H) 3.18 (t, /=8.79 Hz, 2 H) 4.32 – 4.44 (m, 6 H) 4.49 (s, 2 H) 4.54 (t, J=8.79 Hz, 2 H) 6.75 (d; /=8.20 Hz, 1 H) 7.07 (dd, J=8.20, 1.95 Hz, 1 H) 7.20 (s, 1 H) 7.58 (dd, /=8.50, 1.46 Hz, 1 H) 7.79 (d, /=0.78 Hz, 1 H) 7.87 (d, /=8.59 Hz, 1 H); MS (ESI) m/z 527.8 (MHhH)+; Anal. Calcd (%) for C26H27F6N3O2 + 1.0 TFA: C, 52.42; H, 4.40; N, 6.55. Found: C, 52.52; H, 4.27; N 6.18.

As the paragraph descriping shows that 69999-16-2 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; WO2007/91950; (2007); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

Brief introduction of 69999-16-2

69999-16-2 2,3-Dihydrobenzofuranyl-5-acetic acid 2737455, abenzofuran compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.69999-16-2,2,3-Dihydrobenzofuranyl-5-acetic acid,as a common compound, the synthetic route is as follows.

2-(2,3-Dihydro-benzofuran-5-yl)-ethanol Borane-THF complex (1 M) (52ml_, 52mmol) was slowly added to a solution of 2,3- dihydro-5-benzofuranacetic acid (4.62g, 25.9mmol) in 15OmL dry THF cooled to O0C under a nitrogen atmosphere. The reaction mixture was allowed to warm up to RT and stirred for 2Oh. Water (5OmL) was added, and the mixture stirred for 20 min. Ethyl acetate was added and the phases were separated. The aqueous layer was further extracted with ethyl acetate, the combined organic layers were dried (MgSO4) and concentrated to give the title product as light brown viscous oil. Yield: 4.2g (100%) LC-MS (Method 2): Rt 2.37 mins, molecular ion not observed.

69999-16-2 2,3-Dihydrobenzofuranyl-5-acetic acid 2737455, abenzofuran compound, is more and more widely used in various.

Reference£º
Patent; ARGENTA DISCOVERY LTD.; WO2008/96093; (2008); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem