Trifluoroacetic acid → 4-(1-Phenylcyclopropylamino)-6-(3-(piperazin-1-yl)phenylamino)nicotinamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-chloro-4-(1-phenylcyclopropylamino)nicotinamide (150 mg, 0.522 mmol) in p-Dioxane (4.5 mL) was added tert-butyl 4-(3-aminophenyl)piperazine-1-carboxylate (174 mg, 0.626 mmol), Pd(OAc)2 (23 mg, 0.104 mmol), BINAP (65 mg, 0.104 mmol) and Cs2CO3 (510 mg, 1.566 mmol). After stirred at 80° C. for 15 h, it was concentrated to give crude residue, which was then treated with TFA in DCM, 30 min later, the solution was concentrated, the residue was purified by preparative HPLC to give 4-(1-phenylcyclopropylamino)-6-(3-(piperazin-1-yl)phenylamino)nicotinamide. MS found for C25H28N6O as (M+H)+ 429.4. UV: λ=254.6 nm. 1H NMR: (CD3OD) δ 8.17 (s, 1H), 7.31-7.20 (m, 4H), 7.13 (m, 2H), 6.95 (dd, J=8.0, 2.0 Hz, 1H), 6.79 (t, J=2.0 Hz, 1H), 6.60 (dd, J=7.2, 2.0 Hz, 1H), 6.12 (s, 1H), 3.34 (m, 8H), 1.36 (m, 4H) ppm.

Provenance & Evidence