HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 2-((2-Chloro-5-cyano-3-(2-oxopiperazin-1-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Tert-butyl 4-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-oxopiperazine-1-carboxylate | HCID 89923358 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-((2-Chloro-5-cyano-3-(2-oxopiperazin-1-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile | HCID 89922699 | 69.2% |
Reaction Steps
TFA (2 mL) was added to a solution of tert-butyl 4-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-oxopiperazine-1-carboxylate (85 mg, 0.127 mmol) in DCM (4 mL) and the reaction mixture was stirred at room temperature for 1 h. Solvent was evaporated and the crude was dried under vacuum for 10 min. The crude was dissolved in MeOH and neutralized with 7N ammonia in methanol. After stirring for 10 min it was concentrated and purification via flash chromatography (0-10% MeOH in DCM, 12 g) gave 2-((2-chloro-5-cyano-3-(2-oxopiperazin-1-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (50 mg) as a light yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09273057B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-ac441fc9c6484885b870808ec8e6575d |
| Source note | uspto-grants-2016_03 |