Pyridine → HCID 10649831, compound

HRID 1290191Notes

Reaction equation

HRID 1290191 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([N:20]([C:22](=[O:25])[CH2:23][NH2:24])[CH3:21])[C:14]=3[Cl:26])[C:5]2=[N:4][C:3]=1[CH3:27].N1C=CC=CC=1.[C:34](Cl)(=[O:37])[CH2:35][CH3:36]>C(Cl)Cl>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([N:20]([CH3:21])[C:22](=[O:25])[CH2:23][NH:24][C:34](=[O:37])[CH2:35][CH3:36])[C:14]=3[Cl:26])[C:5]2=[N:4][C:3]=1[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 10790603HCID 10790603, compound

Product 1

HCID 10649831HCID 10649831, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-bromo-8-[2,6-dichloro-3-(N-glycyl-N-methylamino)benzyloxy]-2-methylimidazo[1,2-a]pyridine (100 mg), pyridine (25 mg) and methylene chloride (2 ml) was added propionyl chloride (0.02 ml) at ambient temperature and the mixture was stirred at the same temperature for 30 minutes. The mixture was partitioned between methylene chloride and water, and the organic layer was washed with water, dried over magnesium sulfate and concentrated in vacuo to give 3-bromo-8-[2,6-dichloro-3-[N-methyl-N-(propionylglycyl)amino]benzyloxy]-2-methylimidazo[1,2-a]pyridine (111 mg).

Workup

  1. customThe mixture was partitioned between methylene chloride and water
  2. washthe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1140cab61d30445bb04c369aa1e68719
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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