3-(Dimethylcarbamoyl)benzeneboronic acid → 3-{2-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-6-fluoro-1,2,3,4-tetrahydroisoquinolin-7-yl}-N,N-dimethylbenzamide

HRID 2090469Notes

Reaction equation

HRID 2090469 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:12]3[CH:17]=[C:16]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)[N:15]=[C:14]([NH2:25])[N:13]=3)[CH2:9]2)=[CH:4][C:3]=1[F:26].[CH3:27][N:28]([CH3:40])[C:29]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)=[O:30]>>[NH2:25][C:14]1[N:13]=[C:12]([N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:2]([C:35]4[CH:36]=[C:31]([CH:32]=[CH:33][CH:34]=4)[C:29]([N:28]([CH3:40])[CH3:27])=[O:30])=[C:3]([F:26])[CH:4]=3)[CH2:9]2)[CH:17]=[C:16]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)[N:15]=1

Participants

3

Reactant 2

HCID 27733923-(Dimethylcarbamoyl)benzeneboronic acidHCID 594023364-(7-bromo-6-fluoro-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine

Product 1

HCID 594023413-{2-[2-Amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-6-fluoro-1,2,3,4-tetrahydroisoquinolin-7-yl}-N,N-dimethylbenzamide

Procedure

This compound was prepared by using procedures analogous to those described for the synthesis of Example 127 starting from 4-(7-bromo-6-fluoro-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine and {3-[(dimethylamino)carbonyl]phenyl}boronic acid (Frontier, Cat. No. D4088). LCMS (M+H)+: m/z=490.2.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-667172fde15b41fb87dd8fd837b860ff
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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