Hydrochloric Acid → N-{3-[(tert-butylamino)methyl]-4-(4-methylpiperazin-1-yl)phenyl}-7-chloroquinolin-4-amine

HRID 1190869Notes

Reaction equation

HRID 1190869 reaction equation
[C:1]([NH:5][CH2:6][C:7]1[CH:8]=[C:9]([CH:11]=[CH:12][C:13]=1[N:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1)[NH2:10])([CH3:4])([CH3:3])[CH3:2].Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([Cl:32])=[CH:29][CH:30]=2)[N:25]=[CH:24][CH:23]=1.Cl>C(#N)C>[C:1]([NH:5][CH2:6][C:7]1[CH:8]=[C:9]([NH:10][C:22]2[C:31]3[C:26](=[CH:27][C:28]([Cl:32])=[CH:29][CH:30]=3)[N:25]=[CH:24][CH:23]=2)[CH:11]=[CH:12][C:13]=1[N:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68664,7-DichloroquinolineHCID 672478243-[(Tert-butylamino)methyl]-4-(4-methylpiperazin-1-yl)aniline

Product 1

HCID 70944811N-{3-[(tert-butylamino)methyl]-4-(4-methylpiperazin-1-yl)phenyl}-7-chloroquinolin-4-amineYield 47.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-[(tert-butylamino)methyl]-4-(4-methylpiperazin-1-yl)aniline (60 mg, 0.22 mmol) and 4,7-dichloroquinoline (43 mg, 1 eq) were refluxed overnight in 10 mL of acetonitrile with 0.43 mL of HCl 1M. The reaction mixture was then evaporated and purified by preparative thin-layer chromatography (DCM/MeOH/NH4OH/18/210.1) to yield expected compound as a pale yellow solid (45 mg, 47% yield). m/z (ESI) 438.3 [M+H]+.

Workup

  1. customThe reaction mixture was then evaporated
  2. custompurified by preparative thin-layer chromatography (DCM/MeOH/NH4OH/18/210.1)

Sources & evidence

ORD record
ord-84ed6a46d3bc4c1a967838bf2c26a979
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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