Pyridine → 4-[3-[N-(acetylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-1,2-dimethyl-1H-benzimidazole

HRID 2287555Notes

Reaction equation

HRID 2287555 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([C:7]1[C:8]([Cl:27])=[C:9]([C:23]([Cl:26])=[CH:24][CH:25]=1)[CH2:10][O:11][C:12]1[C:20]2[N:19]=[C:18]([CH3:21])[N:17]([CH3:22])[C:16]=2[CH:15]=[CH:14][CH:13]=1)[CH3:6])=[O:4].N1C=CC=CC=1.[C:34](OC(=O)C)(=[O:36])[CH3:35]>ClCCl>[C:34]([NH:1][CH2:2][C:3]([N:5]([C:7]1[C:8]([Cl:27])=[C:9]([C:23]([Cl:26])=[CH:24][CH:25]=1)[CH2:10][O:11][C:12]1[C:20]2[N:19]=[C:18]([CH3:21])[N:17]([CH3:22])[C:16]=2[CH:15]=[CH:14][CH:13]=1)[CH3:6])=[O:4])(=[O:36])[CH3:35]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 154621764-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-1,2-dimethyl-1H-benzimidazole

Product 1

HCID 154621774-[3-[N-(acetylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-1,2-dimethyl-1H-benzimidazoleYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[3-(N-glycyl-N-methylamino) -2,6-dichlorobenzyloxy]-1,2-dimethyl-1H-benzimidazole (80 mg) in dichloromethane (0.8 ml) were added pyridine (23.3 mg) and acetic anhydride (30.1 mg) at ambient temperature, and the mixture was stirred for 1 hour at the same temperature. The solvent was removed with toluene azeotropically three times. The residue was purified by preparative thin layer chromatography (dichloromethane:methanol=10:1, v/v) to give 4-[3-[N-(acetylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-1,2-dimethyl-1H-benzimidazole (75 mg).

Workup

  1. customThe solvent was removed with toluene azeotropically three times
  2. customThe residue was purified by preparative thin layer chromatography (dichloromethane

Sources & evidence

ORD record
ord-b77739c162be47e98a90e5fc4b1af264
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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