Pyridine → HCID 18704953, compound

HRID 2287463Notes

Reaction equation

HRID 2287463 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([C:7]1[C:8]([Cl:32])=[C:9]([C:28]([Cl:31])=[CH:29][CH:30]=1)[CH2:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19]([CH3:22])[CH:18]=[C:17]2[N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)[CH3:6])=[O:4].[C:33](OC(=O)C)(=[O:35])[CH3:34].N1C=CC=CC=1>ClCCl>[C:33]([NH:1][CH2:2][C:3]([N:5]([C:7]1[C:8]([Cl:32])=[C:9]([C:28]([Cl:31])=[CH:29][CH:30]=1)[CH2:10][O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19]([CH3:22])[CH:18]=[C:17]2[N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)[CH3:6])=[O:4])(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 18704968HCID 18704968, compound

Product 1

HCID 18704953HCID 18704953, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-4-(imidazol-1-yl)-2-methylquinoline (60 mg) in dichloromethane (0.6 ml) were added acetic anhydride (15.6 mg) and pyridine (15.1 mg) at ambient temperature, and the mixture was stirred for 3 hours at the same temperature. The mixture was concentrated in vacuo, and the residue was purified by preparative thin layer chromatography (chloroform:methanol, 10:1, v/v) to give 8-[3-(N-(acetylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-4-(imidazol-1-yl)-2-methylquinoline (53 mg) as colorless amorphous.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by preparative thin layer chromatography (chloroform

Sources & evidence

ORD record
ord-e30a6b1d035c46dc9a5e607607567e87
Source dataset
uspto-grants-2000_07
Patent number
US06083959

Reaction notes

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