HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → N1-(7-(3,5-dimethylisoxazol-4-yl)-8-methoxy-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-imidazo[4,5-c]quinolin-2-yl)ethane-1,2-diamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | N-Boc-2-isothiocyanatoethylamine | HCID 4219896 | — |
| Reactant | 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-((tetrahydro-2H-pyran-4-yl)methyl)quinoline-3,4-diamine | HCID 70981155 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N1-(7-(3,5-dimethylisoxazol-4-yl)-8-methoxy-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-imidazo[4,5-c]quinolin-2-yl)ethane-1,2-diamine | HCID 66571286 | 31% |
Reaction Steps
From 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-((tetrahydro-2H-pyran-4-yl)methyl)quinoline-3,4-diamine (for a preparation see Intermediate 17) (70 mg) and 1,1-dimethylethyl (2-isothiocyanatoethyl)carbamate (50 mg). The crude product isolated was treated with TFA (2 ml) in DCM (10 ml), the mixture stirred for 1 h, then evaporated in vacuo. The residue was dissolved in DMSO (1 ml) and purified by MDAP (HpH method) to give the title compound as a beige solid (26 mg, 31%). LCMS (HpH) Rt 0.73 min, MH+ 451
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08846709B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-354f8049fffb41e2823bfd8969164ef5 |
| Source note | uspto-grants-2014_09 |