Hydrochloric Acid → HCID 70944851, compound

HRID 1190881Notes

Reaction equation

HRID 1190881 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH2:16][N:17]2[CH2:22][CH2:21][O: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:24]1[C:33]2[C:28](=[CH:29][C:30]([Cl:34])=[CH:31][CH:32]=2)[N:27]=[CH:26][CH:25]=1.Cl>C(#N)C>[Cl:34][C:30]1[CH:29]=[C:28]2[C:33]([C:24]([NH:5][C:4]3[CH:6]=[C:7]([CH2:16][N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[C:8]([N:9]4[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]4)=[C:2]([CH3:1])[CH:3]=3)=[CH:25][CH:26]=[N:27]2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68664,7-DichloroquinolineHCID 67247561HCID 67247561, compound

Product 1

HCID 70944851HCID 70944851, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Methyl-4-(4-methylpiperazin-1-yl)-5-(morpholin-4-ylmethyl)aniline (79 mg, 0.26 mmol) and 4,7-dichloroquinoline (56 mg, 1.1 eq) were refluxed overnight in 5 mL of acetonitrile with 0.78 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 pale yellow solid (75 mg, 62% yield). m/z (ESI) 466.4 [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-73a3413855b740a39599019625bcd466
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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