Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Propylamine | HCID 7852 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | HCID 66653176 | HCID 66653176 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66653216 | HCID 66653216 | 98.3% |
Reaction Steps
0.108 g (0.37 mmol) of triphosgene diluted in 1 ml of dioxane is added, under an inert atmosphere at ambient temperature, to 0.2 g (0.52 mmol) of methyl 2-amino-5-{[1-(2-methoxyethoxy)-2-methylindolizin-3-yl]carbonyl}benzoate in 5 ml of dioxane. The reaction medium is stirred for 1 hour at ambient temperature and then 0.22 ml (1.57 mmol) of triethylamine and 0.09 ml (1.05 mmol) of n-propylamine are added. After stirring for 18 hours, the reaction medium is hydrolysed with water. The aqueous phase is extracted with dichloromethane. The organic phase obtained is dried over sodium sulphate, filtered, and concentrated under reduced pressure. The solid obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (95/5) mixture. 170 mg of a yellow solid are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08859544B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-ec4f253fddc846fb8f77bcf2833ef244 |
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| Source note | uspto-grants-2014_10 |
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