HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 1-(2-(2-(5-Chloro-2-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | tert-Butyl 4-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate | HCID 86712301 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-(2-(2-(5-Chloro-2-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide | HCID 73296712 | 21% |
Reaction Steps
TFA (1 mL) was added to a solution of tert-butyl 4-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-chloropyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate A20 (0.021 g, 0.037 mmol) in DCM (5 mL) and the mixture was stirred for 16 hours. The volatiles were removed in vacuo and the resultant residue loaded onto a SCX cartridge (5 g). The cartridge was washed with MeOH (100 mL) and then with 5% NH4OH in MeOH (100 mL). The basic fractions were combined, the solvent was removed in vacuo and the resultant residue purified by prep-LCMS to give the title compound 17 as a yellow solid (3.6 mg, 21%). LCMS-B: rt 4.711 min; m/z 466.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09238644B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-91cf6715484d4f1a84ead442c674d9b0 |
| Source note | uspto-grants-2016_01 |