4,7-Dichloroquinoline → {5-[(7-Chloroquinolin-4-yl)amino]-2-(4-methylpiperazin-1-yl)phenyl}methanol

HRID 1190871Notes

Reaction equation

HRID 1190871 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[C:6]([CH2:8][OH:9])[CH:7]=1.Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24]([Cl:28])=[CH:25][CH:26]=2)[N:21]=[CH:20][CH:19]=1>C(O)CCCC>[Cl:28][C:24]1[CH:23]=[C:22]2[C:27]([C:18]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([N:10]4[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]4)=[C:6]([CH2:8][OH:9])[CH:7]=3)=[CH:19][CH:20]=[N:21]2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 68664,7-DichloroquinolineHCID 36995517(5-Amino-2-(4-methylpiperazin-1-yl)phenyl)methanol

Product 1

HCID 67248956{5-[(7-Chloroquinolin-4-yl)amino]-2-(4-methylpiperazin-1-yl)phenyl}methanolYield 83%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

[5-amino-2-(4-methylpiperazin-1-yl)phenyl]methanol (100 mg, 0.45 mmol) and 4,7-dichloroquinoline (94 mg, 1.1 eq) were refluxed in 1 mL of n-pentanol overnight. The reaction mixture was then evaporated and purified by flash chromatography (DCM/MeOH/NH4OH//8/2/0.1) to yield expected compound as a pale brown solid (143 mg, 83% yield). m/z (ESI) 383.1 [M+H]+;

Workup

  1. customThe reaction mixture was then evaporated
  2. custompurified by flash chromatography (DCM/MeOH/NH4OH//8/2/0.1)

Sources & evidence

ORD record
ord-cb39406b166340d3aeca2878dd4dae34
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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