Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Methoxy-2,2-dimethylpropionic acid chloromethyl ester | HCID 14459693 | — |
| Reactant | N-[1-amino-1-(4-{[[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}phenyl)methylidene]benzamide | HCID 136334022 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68212999 | HCID 68212999 | 35.8% |
Reaction Steps
To a mixture of N-[1-amino-1-(4-{[[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}phenyl)methylidene]benzamide (Example 1a, 45 mg) and DMF (2 mL), cesium carbonate (29 mg) and 3-methoxy-2,2-dimethylpropionic acid chloromethyl ester (20 mg) were sequentially added, and the resulting mixture was stirred at 60° C. for 4 hours. The resulting mixture was poured into ethyl acetate (30 mL) and water (20 mL). After shaking the mixture, the organic layer was collected. The organic layer was sequentially washed twice with water (30 mL) and with saturated aqueous sodium chloride solution (20 mL), and dried over anhydrous magnesium sulfate. The resulting mixture was filtered, and the filtrate obtained was concentrated under reduced pressure. The residue obtained was purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate) to obtain the captioned compound (20 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08436009B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-527ceb6ba360489dacf24700108e7804 |
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| Source note | uspto-grants-2013_05 |
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