HCID 178429948, compound → 3-Fluoro-4-(4-methylpiperazin-1-yl)aniline

HRID 2236746Notes

Reaction equation

HRID 2236746 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)=[C:18]([F:29])[CH:17]=1.BrC1C=C2C(=CC=1)[C:37](=[O:41])NC(=O)C2=CNC1C=CC(N2CC(C)NC(C)C2)=CC=1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]/[O:41][CH3:37].[F:29][C:18]1[CH:17]=[C:16]([NH2:15])[CH:21]=[CH:20][C:19]=1[N:22]1[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]1

Participants

5

Reactant 2

HCID 178429948HCID 178429948, compoundHCID 178480721HCID 178480721, compound

Product 2

HCID 27830553-Fluoro-4-(4-methylpiperazin-1-yl)anilineHCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using the procedure described for the preparation of 4Z)-6-bromo-4-({[4-(3,5-dimethylpiperazin-1-yl)phenyl]amino}methylene)isoquinoline-1,3(2H,4H)-dione, 3.0 g (92.0% yield) of light brown solid is obtained from 2.0 g (7.09 mmol) of (4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione and 1.63 g (7.8 mmol) of [3-fluoro-4-(4-methylpiperazin-1-yl)phenyl]amine and 25 mL of N,N-dimethylformamide: mp 206-207° C.; MS (ESI) m/z 459.0-461.0 (M+H)+1

Sources & evidence

ORD record
ord-95d52143a1114fcebc8b55d766d69d91
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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