HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid Mixture with Hydrobromic Acid → (S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid Mixture with Hydrobromic Acid | HCID 21893785 | — |
| Reactant | (S)-benzyl 2-(8-amino-1-(4-(pyridin-2-ylcarbamoyl)phenyl)imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate | HCID 71233862 | — |
| Solvent | Water | HCID 962 | — |
| Product | (S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide | HCID 71226368 | 58.3% |
Reaction Steps
To (S)-benzyl 2-(8-amino-1-(4-(pyridin-2-ylcarbamoyl)phenyl)imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate (0.146 mmol, 78 mg) was added a 33% hydrobromic acid/acetic acid solution (11.26 mmol, 2 ml) and the mixture was left at room temperature for 1 hour. The mixture was diluted with water and extracted with dichloromethane. The aqueous phase was neutralized using 2N sodium hydroxide solution, and then extracted with dichloromethane. the organic layer was dried over magnesium sulfate, filtered and evaporated to give 34 mg of (S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide (58%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09290504B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-3f79b69ef96641b59b692d5db606978a |
| Source note | uspto-grants-2016_03 |