Hydrochloric Acid → HCID 53328146, compound

HRID 1190879Notes

Reaction equation

HRID 1190879 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:8]=1[N:9]1[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1)[NH2:5].Cl[C:23]1[C:32]2[C:27](=[CH:28][C:29]([Cl:33])=[CH:30][CH:31]=2)[N:26]=[CH:25][CH:24]=1.Cl>C(#N)C>[Cl:33][C:29]1[CH:28]=[C:27]2[C:32]([C:23]([NH:5][C:4]3[CH:6]=[C:7]([CH2:16][N:17]4[CH2:21][CH2:20][CH2:19][CH2:18]4)[C:8]([N:9]4[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]4)=[C:2]([CH3:1])[CH:3]=3)=[CH:24][CH:25]=[N:26]2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68664,7-DichloroquinolineHCID 53328351HCID 53328351, compound

Product 1

HCID 53328146HCID 53328146, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Methyl-4-(4-methylpiperazin-1-yl)-5-(pyrrolidin-1-ylmethyl)aniline (70 mg, 0.24 mmol) and 4,7-dichloroquinoline (50 mg, 1 eq) were refluxed overnight in 5 mL of acetonitrile with 1.25 mL of HCl 1M. The reaction mixture was then evaporated and purified by flash chromatography (DCM/MeOH/NH4OH//9/1/0.1) to yield expected compound as a white solid (92 mg, 84% yield). m/z (ESI) 450.1 [M+H]+;

Workup

  1. customThe reaction mixture was then evaporated
  2. custompurified by flash chromatography (DCM/MeOH/NH4OH//9/1/0.1)

Sources & evidence

ORD record
ord-9f0e71de95ec463181e6d5e8448e69f9
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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