7-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinoline → 4-Amino-8-(isoquinolin-7-yl)-7-methylcinnoline-3-carboxamide

HRID 2203227Notes

Reaction equation

HRID 2203227 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][N:15]=[CH:16]3)=[CH:11][CH:10]=2)O1.[NH2:20][C:21]1[C:30]2[C:25](=[C:26](Br)[C:27]([CH3:31])=[CH:28][CH:29]=2)[N:24]=[N:23][C:22]=1[C:33]([NH2:35])=[O:34]>>[NH2:20][C:21]1[C:30]2[C:25](=[C:26]([C:9]3[CH:18]=[C:17]4[C:12]([CH:13]=[CH:14][N:15]=[CH:16]4)=[CH:11][CH:10]=3)[C:27]([CH3:31])=[CH:28][CH:29]=2)[N:24]=[N:23][C:22]=1[C:33]([NH2:35])=[O:34]

Participants

3

Reactant 2

HCID 251049727-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolineHCID 898252134-Amino-8-bromo-7-methylcinnoline-3-carboxamide

Product 1

HCID 717655864-Amino-8-(isoquinolin-7-yl)-7-methylcinnoline-3-carboxamide

Procedure

The title compound was prepared in a manner similar to EXAMPLE 1 using 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinoline and 4-amino-8-bromo-7-methylcinnoline-3-carboxamide. 1H NMR (500 MHz, CD3OD) δ ppm 2.30-2.36 (m, 3 H), 7.72-7.79 (m, 2 H), 7.94 (d, J=5.86 Hz, 1 H), 8.07-8.14 (m, 2 H), 8.22-8.31 (m, 1 H), 8.46-8.52 (m, 1 H), 9.29 (s, 1 H); ESI-MS m/z [M+H]+ 330.4.

Sources & evidence

ORD record
ord-339f0c7bd51845e79c1c0c695f0fb35f
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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