Water → HCID 19603331, compound

HRID 1604567Notes

Reaction equation

HRID 1604567 reaction equation
Br[CH2:2][C:3]([NH:5][CH2:6][C:7]([N:9]([C:11]1[C:12]([Cl:31])=[C:13]([C:27]([Cl:30])=[CH:28][CH:29]=1)[CH2:14][O:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23]([CH3:26])[CH:22]=[CH:21]2)[CH3:10])=[O:8])=[O:4].[N+:32]([C:35]1[CH:40]=[CH:39][C:38]([N:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)=[CH:37][CH:36]=1)([O-:34])=[O:33].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:31][C:12]1[C:11]([N:9]([CH3:10])[C:7](=[O:8])[CH2:6][NH:5][C:3](=[O:4])[CH2:2][N:44]2[CH2:45][CH2:46][N:41]([C:38]3[CH:37]=[CH:36][C:35]([N+:32]([O-:34])=[O:33])=[CH:40][CH:39]=3)[CH2:42][CH2:43]2)=[CH:29][CH:28]=[C:27]([Cl:30])[C:13]=1[CH2:14][O:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23]([CH3:26])[CH:22]=[CH:21]2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 804471-(4-Nitrophenyl)piperazineHCID 19603254HCID 19603254, compound

Product 1

HCID 19603331HCID 19603331, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-[3-[N-(bromoacetylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline (90 mg), 4-nitro-1-(1-piperazinyl)benzene (48 mg) and potassium carbonate (94 mg) in dimethylformamide (2 ml) was stirred at ambient temperature for 1 hour and water added thereto. The mixture was extracted with ethyl acetate twice, and the combined organic layer was washed with water, dried and concentrated. The residue was purified by preparative thin-layer chromatography (10% methanol in dichloromethane) to give 8-[2,6-dichloro-3-[N-methyl-N-[2-[4-(4-nitrophenyl)piperazin-1-yl]acetylglycyl]amino]benzyloxy]-2-methylquinoline (44 mg).

Workup

  1. extractionThe mixture was extracted with ethyl acetate twice
  2. washthe combined organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by preparative thin-layer chromatography (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-deda805767f14d7e98738ced193ac04a
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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