HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → (R)-N-(4-(4-(2-amino-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-hydroxyacetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Tetrafluoro-m-phenylenediamine dihydrochloride | HCID 149026 | — |
| Reactant | HCID 68760357 | HCID 68760357 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (R)-N-(4-(4-(2-amino-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-hydroxyacetamide | HCID 44197986 | 91.2% |
Reaction Steps
(R)-tert-Butyl 3-(4-chlorophenyl)-1-(4-(3-(2-hydroxyacetamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-1-oxopropan-2-ylcarbamate (0.040 g, 0.072 mmol) was placed in DCM (3 mL) at room temperature. TFA (0.5 mL) was then added, and the reaction was stirred at room temperature for 1 hour. The reaction was then concentrated to dryness, and the resulting residue was dissolved in minimal DCM. The solution was added dropwise to a stirring solution of 1M HCl in ether. The resulting solid was filtered, washed with ether, and dried to give (R)—N-(4-(4-(2-amino-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-hydroxyacetamide (0.030 g, 79% yield) as the dihydrochloride salt. MS APCI (+) m/z 457 detected.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08841304B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-f09fc74d886b4ac294038238fda77de6 |
| Source note | uspto-grants-2014_09 |