Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Fluorobenzylamine | HCID 67326 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | HCID 57500383 | HCID 57500383 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66653393 | HCID 66653393 | 219.6% |
Reaction Steps
3 g (10.4 mmol) of triphosgene diluted in 40 ml of dioxane are added to 5.57 g (14.9 mmol) of methyl 2-amino-5-[1-bromo(imidazo[1,5-a]pyridin-3-yl)carbonyl]benzoate in 160 ml of dioxane, under an inert atmosphere. The reaction medium is refluxed for 1 hour. 3.7 g (0.030 mol) of 4-fluorobenzylamine and 6.22 ml (0.045 mol) of triethylamine are added at ambient temperature. The reaction medium is stirred for 4 hours at ambient temperature and then hydrolysed with water. The precipitate obtained is filtered off, rinsed with water, and dried under reduced pressure at 50° C. overnight. The solid obtained is taken up with methanol, filtered, rinsed with methanol, and dried under reduced pressure overnight. 12 g of a yellow solid are obtained (yield=95.5%).
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-af7c8520f6454eb09ef8e8ff15dca157 |
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| Source note | uspto-grants-2014_06 |
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