HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 1-(2-(2-(2-((4-(1-Aminoethyl)phenyl)amino)-5-chloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | tert-Butyl (1-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino)phenyl)ethyl)carbamate | HCID 73296872 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-(2-(2-(2-((4-(1-Aminoethyl)phenyl)amino)-5-chloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide | HCID 86712303 | 93.8% |
Reaction Steps
To a solution of tert-butyl (1-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino)phenyl)ethyl)carbamate 24 (0.012 g, 0.022 mmol) in DCM (1 mL) was added trifluoroacetic acid (0.5 mL). The mixture was stirred at ambient temperature for 2 hours before the volatiles were removed in vacuo. The crude residue was loaded onto an SCX cartridge conditioned with methanol. The cartridge was washed with methanol and then 2 N ammonia in ethanol. The basic fractions were combined and the solvent removed in vacuo to give the title compound 24A as a colourless oil (0.009 g, 92%). LCMS-C: rt 4.41 min; m/z 436 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09238644B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-3c96f7942432498786a0803eaca01506 |
| Source note | uspto-grants-2016_01 |