1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 8-[2,6-Dichloro-3-[4-[4-(methylcarbamoyl)cinnamoyl]piperazine-1-carbonyl]benzyloxy]-2-methylquinoline

HRID 1871149Notes

Reaction equation

HRID 1871149 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.[CH3:32][NH:33][C:34]([C:36]1[CH:46]=[CH:45][C:39]([CH:40]=[CH:41][C:42](O)=[O:43])=[CH:38][CH:37]=1)=[O:35].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[Cl:3][C:4]1[C:22]([C:23]([N:25]2[CH2:26][CH2:27][N:28]([C:42](=[O:43])[CH:41]=[CH:40][C:39]3[CH:45]=[CH:46][C:36]([C:34](=[O:35])[NH:33][CH3:32])=[CH:37][CH:38]=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

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 183219628-[2,6-Dichloro-3-(piperazine-1-carbonyl)benzyloxy]-2-methylquinoline dihydrochlorideHCID 534120223-[4-(Methylcarbamoyl)phenyl]prop-2-enoic acid

Product 1

HCID 539472038-[2,6-Dichloro-3-[4-[4-(methylcarbamoyl)cinnamoyl]piperazine-1-carbonyl]benzyloxy]-2-methylquinolineYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-[2,6-dichloro-3-(piperazine-1-carbonyl)benzyloxy]-2-methylquinoline dihydrochloride (60 mg), 4-(methylcarbamoyl)cinnamic acid (26.9 mg) and 1-hydroxybenzotriazole (22.6 mg) in N,N-dimethylformamide (0.6 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (27.4 mg) at ambient temperature, and the mixture was stirred for 3 hours at the same temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated sodium bicarbonate solution, 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)cinnamoyl]piperazine-1-carbonyl]benzyloxy]-2-methylquinoline (73 mg) as colorless amorphous.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated sodium bicarbonate solution, 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-6be002d4a32e4e988e2e1d4f86661f2a
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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