Water → 8-[2,6-Dichloro-3-[4-(4-(methylcarbamoyl)phenylcarbamoyl]piperazine-1-carbonyl]benzyloxy]-2-methylquinoline

HRID 1871151Notes

Reaction equation

HRID 1871151 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:22]([C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[O:24])=[CH:21][CH:20]=[C:19]([Cl:31])[C:5]=1[CH2:6][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([CH3:18])[CH:14]=[CH:13]2.C(N(CC)CC)C.[CH3:39][NH:40][C:41]([C:43]1[CH:48]=[CH:47][C:46]([NH:49][C:50](=O)[O:51]C2C=CC=CC=2)=[CH:45][CH:44]=1)=[O:42].O>CN(C)C=O>[Cl:3][C:4]1[C:22]([C:23]([N:25]2[CH2:26][CH2:27][N:28]([C:50](=[O:51])[NH:49][C:46]3[CH:45]=[CH:44][C:43]([C:41](=[O:42])[NH:40][CH3:39])=[CH:48][CH:47]=3)[CH2:29][CH2:30]2)=[O:24])=[CH:21][CH:20]=[C:19]([Cl:31])[C:5]=1[CH2:6][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([CH3:18])[CH:14]=[CH:13]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 18321944Phenyl 4-(methylcarbamoyl)phenylcarbamateHCID 183219628-[2,6-Dichloro-3-(piperazine-1-carbonyl)benzyloxy]-2-methylquinoline dihydrochloride

Product 1

HCID 183217598-[2,6-Dichloro-3-[4-(4-(methylcarbamoyl)phenylcarbamoyl]piperazine-1-carbonyl]benzyloxy]-2-methylquinolineYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 8-[2,6-dichloro-3-(piperazine-1-carbonyl)benzyloxy]-2-methylquinoline dihydrochloride (60 mg) and triethylamine (48.3 mg) in N,N-dimethylformamide (0.6 ml) was added phenyl 4-(methylcarbamoyl)phenylcarbamate (33.8 mg), and the mixture was stirred for 2 hours at 80° C. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (chloroform:methanol=10:1, V/V) to give 8-[2,6-dichloro-3-[4-(4-(methylcarbamoyl)phenylcarbamoyl]piperazine-1-carbonyl]benzyloxy]-2-methylquinoline (61 mg) as colorless amorphous.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (chloroform:methanol=10:1, V/V)

Sources & evidence

ORD record
ord-af30712b7f5b47d78b06f90863bb5040
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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