O-Phenylenediamine → 2,3-Dihydro-4-[2-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-5-yl]-1H-[1,5]benzodiazepin-2-one
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].[CH3:9][C:10]1[N:11]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH2:27][C:28](OCC)=[O:29])=O)=[CH:21][N:20]=2)[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=1>>[CH3:9][C:10]1[N:11]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH2:27][C:28](=[O:29])[NH:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[N:1]=3)=[CH:21][N:20]=2)[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:18]=1Participants
3
Procedure
The procedure of Example 1 was followed using 1,2-diaminobenzene (86 mg, 0.76 mmol) and ethyl 2-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-5-oylacetate (260 mg, 0.80 mmol). The crude product was purified by flash chromatography (eluting with ethyl acetate/methanol =6:1), followed by recrystallisation from acetone to give the title compound (40 mg, 14%) as a buff solid, m.p. 208°-210° C..
Workup
- customThe crude product was purified by flash chromatography (eluting with ethyl acetate/methanol =6:1)