(Isoquinolin-6-yl)boronic acid → 4-Amino-8-(isoquinolin-6-yl)-7-methylcinnoline-3-carboxamide

HRID 2203228Notes

Reaction equation

HRID 2203228 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7](B(O)O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=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:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[CH:1]=[N:2][CH:3]=[CH:4]4)[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 44119669(Isoquinolin-6-yl)boronic acidHCID 898252134-Amino-8-bromo-7-methylcinnoline-3-carboxamide

Product 1

HCID 717655464-Amino-8-(isoquinolin-6-yl)-7-methylcinnoline-3-carboxamide

Procedure

The title compound was prepared in a manner similar to EXAMPLE 1 using isoquinolin-6-ylboronic acid and 4-amino-8-bromo-7-methylcinnoline-3-carboxamide. 1H NMR (500 MHz, CD3OD) δ ppm 2.34 (s, 3 H), 7.67 (d, J=8.30 Hz, 1 H), 7.76 (d, J=8.79 Hz, 1 H), 7.90 (d, J=5.86 Hz, 1 H), 7.94 (s, 1 H), 8.28 (t, J=8.30 Hz, 2 H), 8.50 (d, J=5.86 Hz, 1H), 9.35 (s, 1 H); ESI-MS m/z [M+H]+ 330.4.

Sources & evidence

ORD record
ord-4a5336d5030d43db8c321ccce177a0ad
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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