Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1-Chloro-N,N-2-trimethylpropenylamine | HCID 640792 | — |
| Reactant | 8-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid | HCID 86717872 | — |
| Reactant | HCID 118308755 | HCID 118308755 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 90192599 | HCID 90192599 | 23.7% |
Reaction Steps
To a mixture of 167 mg of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid and 1.5 ml of dichloromethane was added 90 μl of 1-chloro-N,N,2-trimethylprop-1-en-1-amine under ice-cooling, followed by stirring at room temperature for 30 minutes. A solution of 93 mg of ethyl 2-amino-2-(pyrimidin-5-yl)propanoate in 1.5 ml of dichloromethane and 0.15 ml of triethylamine were added thereto under ice-cooling, followed by stirring at room temperature for 2 hours. To the reaction mixture was added water, followed by extraction with chloroform. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 56 mg of ethyl 2-[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]-2-(pyrimidin-5-yl)propanoate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09278968B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-bc45c0abea1d4f6597de33f061d62722 |
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| Source note | uspto-grants-2016_03 |
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