Water → HCID 10743570, compound

HRID 1290185Notes

Reaction equation

HRID 1290185 reaction equation
[H-].[Na+].[Br:3][C:4]1[N:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[C:17]([N:22]([C:24](=[O:27])[CH2:25][OH:26])[CH3:23])[C:16]=3[Cl:28])[C:7]2=[N:6][C:5]=1[CH3:29].[CH3:30]I.O>CN(C)C=O>[Br:3][C:4]1[N:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[C:17]([N:22]([C:24](=[O:27])[CH2:25][O:26][CH3:30])[CH3:23])[C:16]=3[Cl:28])[C:7]2=[N:6][C:5]=1[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 10838214HCID 10838214, compound

Product 1

HCID 10743570HCID 10743570, compoundYield 19.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60% in oil, 9 mg) in N,N-dimethylformamide (1 ml) was added 3-bromo-8-[2,6-dichloro-3-(N-glycoloyl-N-methylamino)benzyloxy]-2-methylimidazo[1,2-a]pyridine (100 mg). After stirring for 10 minutes, methyl iodide (36 mg) was added thereto and the mixture was stirred at ambient temperature for 1 hour. To this mixture were added methyl iodide (36 mg) and N,N-dimethylformamide (1 ml). The mixture was stirred at 60° C. for additional 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate 3 times. The combined organic layers were washed with water 4 times and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (dichloromethane: methanol=20:1, V/V) followed by crystallization from ethanol-diethyl ether to give 3-bromo-8-[3-(N-methoxyacetyl-N-methylamino)-2,6-dichlorobenzyloxy]-2-methylimidazo[1,2-a]pyridine (20 mg) as crystals.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 1 hour
  2. stirringThe mixture was stirred at 60° C. for additional 2 hours
  3. extractionextracted with ethyl acetate 3 times
  4. washThe combined organic layers were washed with water 4 times and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by preparative thin-layer chromatography (dichloromethane: methanol=20:1, V/V)
  8. customfollowed by crystallization from ethanol-diethyl ether

Sources & evidence

ORD record
ord-62c0e4ccb87547d69fe189a3f813f296
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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