HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-((4-methoxyazepan-4-yl)methoxy)quinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | tert-Butyl 4-((2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)methyl)-4-methoxyazepane-1-carboxylate | HCID 86654367 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-((4-methoxyazepan-4-yl)methoxy)quinoline | HCID 67230525 | 95% |
Reaction Steps
tert-Butyl 4-((2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)methyl)-4-methoxyazepane-1-carboxylate (0.040 g, 0.079 mmol) was added to a mixture of trifluoroacetic acid and DCM (1:1) for 30 minutes, and the reaction was concentrated. Ethyl acetate was added and the suspension was filtered through a Waters filter (to remove any errant silica gel), and the filtrate was concentrated. DCM was added followed by precipitation with HCl dissolved in diethyl ether, evaporated, co-evaporated in diethyl ether to yield 16 mgs of the desired product as a yellow solid (95% pure by LC). MS ESI (+) m/z 404 (M+1) detected.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08575145B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-76f6edf45cdb4694817f979ac730eb51 |
| Source note | uspto-grants-2013_11 |