Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloride | HCID 312 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Propargylamine | HCID 239041 | — |
| Reactant | HCID 136344252 | HCID 136344252 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 74019988 | HCID 74019988 | 10.2% |
Reaction Steps
To a solution of 0.71 g of 4-hydroxy-3-[3-[3-(methoxycarbonylmethoxy)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone in 5 ml of dimethylformamide was added 0.090 g of sodium hydride (60% oily), and this was stirred at room temperature for 1 hour. 0.46 g of paratoluenesulfonyl chloride was added thereto, this was stirred at room temperature for 4 hours, then, 0.60 g of propargylamine was added, and this was stirred at room temperature overnight. To the reaction solution was added water, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain 0.080 g of 4-propargylamino-3-[3-[3-(methoxycarbonylmethoxy)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone [Compound No. (13b)] as a yellow crystal.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07989478B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-9cd367a8399943be872cc3eb74ce71e3 |
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| Source note | uspto-grants-2011_08 |
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