Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Propylamine | HCID 7852 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | HCID 66653613 | HCID 66653613 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66653584 | HCID 66653584 | 89.8% |
Reaction Steps
0.35 g (1.2 mmol) of triphosgene is added, at ambient temperature under a nitrogen atmosphere, to a suspension of 0.5 g (1.7 mmol) of methyl 2-amino-5-(imidazo[1,5-a]pyridin-3-ylcarbonyl)benzoate in 20 ml of anhydrous dioxane. After heating for 2 hours at 100° C., 0.28 ml (3.4 mmol) of n-propylamine and then 0.71 ml (5 mmol) of triethylamine are added to the reaction medium at ambient temperature. After stirring for 18 hours at ambient temperature, H2O is added. The aqueous phase is extracted with dichloromethane. The organic phase is dried over sodium sulphate, filtered, and concentrated under reduced pressure. The yellow solid obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (98/2) mixture. 0.410 g of a yellow solid is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08759344B2 |
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| Source dataset | uspto-grants-2014_06 |
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| ORD ID | ord-f4c1355a7eba4c9891951cb348a7d71e |
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| Source note | uspto-grants-2014_06 |
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