N-Methylethylenediamine → HCID 19592700, compound

HRID 613535Notes

Reaction equation

HRID 613535 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[C:8]([NH:13][C:14](=[O:23])[C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:22])[CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[CH2:24][CH3:25].CNCCN.ClC1C=CC=C(Cl)C=1[C:34]([NH:36][C:37]1C=CC=C2[C:46]=1[N:45]=[CH:44]C(CC)=C2CNCCNC)=[O:35].C(N1C=CN=C1)(N1C=CN=C1)=O>COCCOC.CN1CCN(C)C1=O.O>[Cl:21][C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:22])[C:15]=1[C:14]([NH:13][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[N:6]=[CH:5][C:4]([CH2:24][CH3:25])=[C:3]2[CH2:2][N:36]1[CH2:37][CH2:46][N:45]([CH3:44])[C:34]1=[O:35])=[O:23]

Participants

8

Reactant 4

HCID 8014N-MethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 19592475HCID 19592475, compoundHCID 19592908HCID 19592908, compound

Product 1

HCID 19592700HCID 19592700, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 66611,3-Dimethyl-2-imidazolidinoneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-chloromethyl-8-(2,6-dichlorobenzoylamino)-3-ethylquinoline (150 mg) and N-methylethylenediamine (141 mg) in 1,2-dimethoxyethane was stirred for 2 hours at 70° C. The mixture was partitioned between dichloroethane and water, and the organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give a residue containing 8-(2,6-dichlorobenzoylamino)-3-ethyl-4-[(2-methylaminoethyl-amino)methyl]quinoline. To the solution of the obtained residue in 1,3-dimethyl-2-imidazolidinone was added 1,1'-carbonyldiimidazole (309 mg), and the mixture was stirred for 30 minutes at 70° C., for 1 hour at 100° C. and for 1 hour at 150° C. Water was added to the mixture, and the resulting precipitates were collected by filtration. The residue was purified by preparative thin layer chromatography (methanol-dichloromethane) and crystallized from isopropyl alcohol to give 8-(2,6-dichlorobenzoylamino)-3-ethyl-4-(3-methyl-2-oxoimidazolidin-1-ylmethyl)quinoline (28.6 mg).

Workup

  1. customThe mixture was partitioned between dichloroethane and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customto give a residue
  6. stirringthe mixture was stirred for 30 minutes at 70° C., for 1 hour at 100° C. and for 1 hour at 150° C
  7. customthe resulting precipitates
  8. filtrationwere collected by filtration
  9. customThe residue was purified by preparative thin layer chromatography (methanol-dichloromethane)
  10. customcrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-03e5ebbb70e64a5db7ea450c337c64d0
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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