[Cl:1][C:2]1[C:8]([N:9]2[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH3:17])[CH3:16])[CH2:10]2)=[CH:7][C:5]([NH2:6])=[C:4]([N+:18]([O-])=O)[CH:3]=1>[Ni].CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:18])[C:5]([NH2:6])=[CH:7][C:8]=1[N:9]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH3:16])[CH3:17])[CH2:10]1A mixture of 4-chloro-5-(3-dimethylaminomethyl-pyrrolidin-1-yl)-2-nitroaniline (630 mg, 2.1 mmol), EtOAc (20 mL) and Ra—Ni (150 mg) was stirred for 2 days at rt under a hydrogen atmosphere (3.0 bar). The catalyst was removed by filtration and the filtrate was concentrated. The crude was purified by chromatography to give the sub-title compound.
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