HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 8-(trans-3-Fluoropiperidin-4-yloxy)-2-(7-(pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)quinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Tert-butyl trans-3-fluoro-4-(2-(7-(pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate | HCID 66781535 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 8-(trans-3-Fluoropiperidin-4-yloxy)-2-(7-(pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)quinoline | HCID 66781580 | 31% |
Reaction Steps
tert-Butyl trans-3-fluoro-4-(2-(7-(pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate (22 mg, 0.041 mmol) was added to 2 ml DCM at ambient temperature. TFA (2 mL) was added and the reaction was stirred for 1 hour, then diluted with DCM and water. The mixture was washed with 1N NaOH amine and extracted with DCM, followed by extraction with 20% IP A/Chloroform. The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by preparative TLC, eluting with 15% MeOH/0.5% NH4OH in DCM to provide the desired product as a film (5.6 mg, 31% yield). MS APCI (+) m/z 440.1 (M+1) detected.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08138181B2 |
| Source dataset | uspto-grants-2012_03 |
| ORD ID | ord-d19d0b46e86044ca8ada5247f96c8f2d |
| Source note | uspto-grants-2012_03 |