Novel benzimidazole compound and pharmaceutical use of same
A compound and pharmaceutical technology, applied in the field of new benzimidazole compounds and their medical uses, can solve the problems of no disclosure and the like
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0613] Example 1: Preparation of 1-[6-(4-fluorophenoxy)-1H-benzimidazol-1-yl]-2-methylpropan-2-alcohol (compound 1)
[0614]
[0615] Step (i): Preparation of 1-[(5-fluoro-2-nitrophenyl)amino]-2-methylpropan-2-ol (Compound 62)
[0616] A mixture of compound 61 (1.59 g), 1-amino-2-methylpropan-2-ol (0.98 g), diisopropylethylamine (5.22 mL) and DMF (50 mL) was stirred at 60 °C for 2 hours . A mixture of water and ethyl acetate / hexane (=1 / 1) was added to the reaction mixture, and the target product was extracted in the organic layer. The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain Compound 62 as a crude product.
[0617] Step (ii): Preparation of 1-[(5-(4-fluorophenoxy)-2-nitrophenyl]amino)-2-methylpropan-2-ol (compound 63)
[0618] A mixture of the crude product of compound 62 prepared in step (i), 4-fluorophenol (1.68 g), cesium carbonate (6.52 g) and NMP (25 mL) was stirred at 100 °C for 2 hours. ...
Embodiment 2
[0625] Example 2: Preparation of 6-(4-fluorophenoxy)-1-(tetrahydrofuran-2-ylmethyl)-1H-benzimidazole (compound 2)
[0626]
[0627] Compound 2 (0.26 g) was prepared according to the method of Example 1 by using the starting material (tetrahydrofuran-2-yl)methanol (0.607 g) instead of 1-amino-2-methylpropan-2-ol.
[0628] 1 H-NMR (DMSO-d6) δ: 1.49 (1H, m), 1.75 (2H, m), 1.94 (1H, m), 3.63 (2H, m), 4.07-4.34 (3H, m), 6.87-6.90 (1H, m), 6.97-7.02 (2H, m), 7.19 (2H, m), 7.35 (1H, m), 7.62 (1H, m), 8.14 (1H, s).
Embodiment 3
[0629] Example 3: Preparation of 6-(4-fluorophenoxy)-1-[2-(prop-2-yloxy)ethyl]-1H-benzimidazole (compound3)
[0630]
[0631] A mixture of compound 65 (0.050 g), sodium hydride (0.011 g) and DMF (1.0 mL), prepared according to Example 1 using appropriate starting materials, was stirred at 0 °C for 30 minutes. To the reaction solution was added 2-bromopropane (0.045 g) and the mixture was further stirred at room temperature for 2 hours. To the reaction mixture were added saturated aqueous ammonium chloride and ethyl acetate, and the target product was extracted in the organic layer. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (eluent: chloroform / methanol = 99 / 1) to obtain Compound 3 (9 mg).
[0632] 1 H-NMR (DMSO-d6) δ: 0.94 (6H, d, J = 6.1 Hz), 3.44 (1H, m), 3.64 (2H, t, J = 5.0 Hz), 4.30 (2H, t, J = 5.0 Hz), 6.87-7.02 (3H, m), 7.18 (2H, m), 7.32...
PUM
| Property | Measurement | Unit |
|---|---|---|
| Extended width | aaaaa | aaaaa |
Abstract
Description
Claims
Application Information
Login to View More 
PatSnap Eureka turns technology decisions into work you can execute. Powered by our Innovation Knowledge Graph, it runs expert workflows across engineering, life sciences, materials and intellectual property. Get your review-ready output in minutes.
