1-Methyl-1H-benzoimidazole-6-boronic acid → 4-amino-7-methyl-8-(1-methyl-1H-benzo[d]imidazol-6-yl)cinnoline-3-carboxamide

HRID 2203226Notes

Reaction equation

HRID 2203226 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8](B(O)O)[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1.[NH2:14][C:15]1[C:24]2[C:19](=[C:20](Br)[C:21]([CH3:25])=[CH:22][CH:23]=2)[N:18]=[N:17][C:16]=1[C:27]([NH2:29])=[O:28]>>[NH2:14][C:15]1[C:24]2[C:19](=[C:20]([C:8]3[CH:9]=[CH:10][C:5]4[N:4]=[CH:3][N:2]([CH3:1])[C:6]=4[CH:7]=3)[C:21]([CH3:25])=[CH:22][CH:23]=2)[N:18]=[N:17][C:16]=1[C:27]([NH2:29])=[O:28]

Participants

3

Reactant 2

HCID 467386791-Methyl-1H-benzoimidazole-6-boronic acidHCID 898252134-Amino-8-bromo-7-methylcinnoline-3-carboxamide

Product 1

HCID 717654304-amino-7-methyl-8-(1-methyl-1H-benzo[d]imidazol-6-yl)cinnoline-3-carboxamide

Procedure

The title compound was prepared in a manner similar to EXAMPLE 1 using (1-methyl-1H-benzo[d]imidazol-6-yl)boronic acid and 4-amino-8-bromo-7-methylcinnoline-3-carboxamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.30 (s, 3 H), 3.83 (s, 3 H), 7.11 (dd, J=8.34, 1.52 Hz, 1 H), 7.49 (d, J=1.01 Hz, 1 H), 7.55 (br s, 1 H), 7.72 (t, J=8.46 Hz, 2 H), 8.22 (s, 1 H), 8.35 (s, 1 H), 8.37 (s, 1 H); ESI-MS m/z [M+H]+ 333.3.

Sources & evidence

ORD record
ord-c248334cab5e4a8091bb118bc5f31e87
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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