Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Monosodium phosphate | HCID 23672064 | — |
| Reactant | [5-Amino-1-(6-fluoro-2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1-benzenesulfonyl-1H-indol-2-yl)methanone | HCID 68160076 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | HCID 66556759 | HCID 66556759 | 91.1% |
Reaction Steps
[5-Amino-1-(6-fluoro-2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1-benzenesulfonyl-1H-indol-2-yl)methanone (114 mg, 0.22 mmol) was dissolved in isopropanol (2.2 ml), and an aqueous solution of 1 M sodium hydroxide (2.2 ml) was added thereto. The resulting mixture was heated at 90° C. with stirring under a nitrogen atmosphere for two hours. After the reaction mixture was cooled to room temperature, water and a saturated aqueous solution of sodium dihydrogen phosphate were added thereto. The product was extracted with ethyl acetate. The organic layer was isolated, washed with an saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. The desiccant was removed by filtration. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (amino silica gel; dichloromethane/methanol=100/5) to give [5-amino-1-(6-fluoro-2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)methanone as a yellow solid (75 mg, 89.8%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08829199B2 |
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| Source dataset | uspto-grants-2014_09 |
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| ORD ID | ord-947cb01e068b47a9a1867db26297735f |
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| Source note | uspto-grants-2014_09 |
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