Pyridine → HCID 10601892, compound

HRID 1290190Notes

Reaction equation

HRID 1290190 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](OC(=O)C)(=[O:36])[CH3:35]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:34]([NH:24][CH2:23][C:22]([N:20]([C:15]1[C:14]([Cl:26])=[C:13]([C:18]([Cl:19])=[CH:17][CH:16]=1)[CH2:12][O:11][C:10]1[C:5]2[N:6]([C:2]([Br:1])=[C:3]([CH3:27])[N:4]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:21])=[O:25])(=[O:36])[CH3:35]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10790603HCID 10790603, compound

Product 1

HCID 10601892HCID 10601892, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-8-[2,6-dichloro-3-(N-glycyl-N-methylamino)benzyloxy]-2-methylimidazo[1,2-a]pyridine (100 mg) in methylene chloride (2 ml) were added pyridine (17 mg), 4-dimethylaminopyridine (10 mg) and acetic anhydride (32 mg), and the mixture was stirred for 1.5 hours. The mixture was washed with water twice and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (methylene chloride:methanol=5:1, V/V) to give 8-[3-[N-(acetylglycyl)-N-methylamino]-2,6-dichlorobenzyloxy]-3-bromo-2-methylimidazo[1,2-a]pyridine (74 mg).

Workup

  1. washThe mixture was washed with water twice
  2. dry with materialbrine, dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (methylene chloride:methanol=5:1, V/V)

Sources & evidence

ORD record
ord-108583b1743c44709299a5e09948d60d
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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