HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 2-((2-chloro-5-cyano-3-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl)amino)-4-(ethylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Anisole | HCID 7519 | — |
| Reactant | 2-((2-chloro-5-cyano-3-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl)amino)-4-(ethyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile | HCID 118253439 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | 2-((2-chloro-5-cyano-3-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl)amino)-4-(ethylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile | HCID 89923263 | 58.1% |
Reaction Steps
2-((2-chloro-5-cyano-3-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl)amino)-4-(ethyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (163 mg, 0.186 mmol) (crude, <=0.190 mmol) was dissolved in ClCH2CH2Cl (10 mL). Anisole (1 ml, 9.15 mmol) and TFA (2 ml, 26.0 mmol) were added and the mixture stirred at room temperature for 3 hours. The reaction mixture was evaporated to a sticky oil, dissolved in DMSO and purified by prep HPLC to give 48.5 mg of 2-((2-chloro-5-cyano-3-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)phenyl)amino)-4-(ethylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09273057B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-1f7c7b032f2640fa9e28d7c7fb6fc05c |
| Source note | uspto-grants-2016_03 |