HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → (S)-2-(4-chlorophenyl)-3-(isopropylamino)-1-(4-(5-(3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Tetrafluoro-m-phenylenediamine dihydrochloride | HCID 149026 | — |
| Reactant | (S)-tert-Butyl 2-(4-chlorophenyl)-3-(4-(5-(3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate | HCID 68760705 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-2-(4-chlorophenyl)-3-(isopropylamino)-1-(4-(5-(3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one | HCID 44198875 | 81% |
Reaction Steps
(S)-tert-Butyl 2-(4-chlorophenyl)-3-(4-(5-(3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate (0.041 g, 0.065 mmol) was placed in DCM (3 mL) at room temperature. TFA (0.3 mL) was then added, and the reaction was stirred at room temperature for 1 hour. The reaction was then concentrated to dryness, dissolved in minimal DCM, and added dropwise to a stirring solution of 1M HCl in ether. The solid product was filtered, washed with ether, and dried to give (S)-2-(4-chlorophenyl)-3-(isopropylamino)-1-(4-(5-(3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one (0.028 g, 81% yield) as the dihydrochloride salt. MS ESI (+) m/z 533 detected.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08841304B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-6b720936b77047d78f1426db8a467d1a |
| Source note | uspto-grants-2014_09 |