1,1'-Carbonyldiimidazole → HCID 19592370, compound

HRID 613553Notes

Reaction equation

HRID 613553 reaction equation
ClC1C2C(=C(N[C:13](=[O:22])C3C(Cl)=CC=CC=3Cl)C=CC=2)N=CC=1.C(NCCN)C1C=CC=CC=1.[CH2:34]([NH:41][CH2:42][CH2:43][NH:44][C:45]1[C:54]2[C:49](=[C:50]([NH:55][C:56](=[O:65])[C:57]3[C:62]([Cl:63])=[CH:61][CH:60]=[CH:59][C:58]=3[Cl:64])[CH:51]=[CH:52][CH:53]=2)[N:48]=[CH:47][CH:46]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.N12CCCN=C1CCCCC2>CN(C)C=O>[CH2:34]([N:41]1[CH2:42][CH2:43][N:44]([C:45]2[C:54]3[C:49](=[C:50]([NH:55][C:56](=[O:65])[C:57]4[C:62]([Cl:63])=[CH:61][CH:60]=[CH:59][C:58]=4[Cl:64])[CH:51]=[CH:52][CH:53]=3)[N:48]=[CH:47][CH:46]=2)[C:13]1=[O:22])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

7

Reactant 5

HCID 682631,1'-CarbonyldiimidazoleHCID 77801N-BenzylethylenediamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19592348HCID 19592348, compoundHCID 195925644-Chloro-8-(2,6-dichlorobenzoylamino)quinoline

Product 1

HCID 19592370HCID 19592370, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-chloro-8-(2,6-dichlorobenzoylamino)quinoline (400 mg) and N-benzylethylenediamine (854 mg) was stirred for 6 hours at 130° C. The mixture was partitioned between ethyl acetate and water, and the organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography on silica gel (methanol-dichloromethane) to give a residue containing 4-(2-benzylaminoethylamino)-8-(2,6-dichlorobenzoylamino)quinoline. A mixture of the obtained residue, 1,1'-carbonyldiimidazole (221 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (191 mg) in dimethylformamide was stirred for 4 hours at ambient temperature and for 2 hours at 130° C. The mixture was partitioned between ethyl acetate and water, and the organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography on silica gel (methanol-dichloromethane) to give 4-(3-benzyl-2-oxoimidazolidin-1-yl)-8-(2,6-dichlorobenzoylamino)quinoline (150 mg).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (methanol-dichloromethane)
  6. customto give a residue
  7. stirringwas stirred for 4 hours at ambient temperature and for 2 hours at 130° C
  8. customThe mixture was partitioned between ethyl acetate and water
  9. washthe organic layer was washed with water and brine
  10. dry with materialdried over magnesium sulfate
  11. customevaporated in vacuo
  12. customThe residue was purified by flash chromatography on silica gel (methanol-dichloromethane)

Sources & evidence

ORD record
ord-eb1b72aa2d0b4f10973f32f5157012c3
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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