6-Bromo-3-methyl-3H-imidazo[4,5-b]pyridine → 4-amino-7-methyl-8-(3-methyl-3H-imidazo[4,5-b]pyridin-6-yl)cinnoline-3-carboxamide
Reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:10]=[CH:9][N:8]([CH3:11])[C:5]2=[N:6][CH:7]=1.[NH2:12][C:13]1[C:22]2[C:17](=[C:18](Br)[C:19]([CH3:23])=[CH:20][CH:21]=2)[N:16]=[N:15][C:14]=1[C:25]([NH2:27])=[O:26]>>[NH2:12][C:13]1[C:22]2[C:17](=[C:18]([C:2]3[CH:3]=[C:4]4[N:10]=[CH:9][N:8]([CH3:11])[C:5]4=[N:6][CH:7]=3)[C:19]([CH3:23])=[CH:20][CH:21]=2)[N:16]=[N:15][C:14]=1[C:25]([NH2:27])=[O:26]Participants
3
Procedure
The title compound was prepared in a manner similar to EXAMPLE 96 using 6-bromo-3-methyl-3H-imidazo[4,5-b]pyridine and 4-amino-8-bromo-7-methylcinnoline-3-carboxamide. 1H NMR (400 MHz, CD3OD) δ ppm 2.34 (s, 3 H), 4.03 (s, 3 H), 7.75 (d, J=8.59 Hz, 1 H), 8.04 (d, J=1.77 Hz, 1 H), 8.28 (d, J=8.59 Hz, 1 H), 8.35 (d, J=1.77 Hz, 1H), 8.45 (s, 1 H); ESI-MS m/z [M+H]+ 334.2.
Sources & evidence
- ORD record
- ord-574c5b5d3b994ef3b1458234ffe73cad
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365566B2
Reaction notes
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