7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-3-nitro-N-((tetrahydro-2H-pyran-4-yl)methyl)quinolin-4-amine → 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-((tetrahydro-2H-pyran-4-yl)methyl)quinoline-3,4-diamine

Participants

Reaction Steps

7-(3,5-Dimethylisoxazol-4-yl)-6-methoxy-3-nitro-N-((tetrahydro-2H-pyran-4-yl)methyl)quinolin-4-amine (for a preparation see Intermediate 16) (1.2 g, 2.91 mmol) was dissolved in a mixture of ethyl acetate (60 ml) and methanol (10 ml) and hydrogenated over Pd/C (0.310 g, 2.91 mmol, 5% w/w, 50% water, Type E101 NO/W) for 24 h at atmospheric pressure under a hydrogen burette. The mixture was filtered and evaporated and the residue was dissolved in DCM (3 ml) and loaded onto a 50 g silica column, then eluted with 0-15% 2M methanolic ammonia/DCM and product containing fractions evaporated in vacuo to give 7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-((tetrahydro-2H-pyran-4-yl)methyl)quinoline-3,4-diamine (0.45 g, 1.177 mmol, 40.4% yield) as a pale yellow solid. LCMS (formate) Rt 0.68 min, MH+ 384

Provenance & Evidence