Ethyl chloroacetate → HCID 67211599, compound

HRID 2068576Notes

Reaction equation

HRID 2068576 reaction equation
Cl[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[NH:26][C:25](=[O:27])[C:24]3[NH:28][CH:29]=[N:30][C:23]=3[CH:22]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[NH:26][C:25](=[O:27])[C:24]3[N:28]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:29]=[N:30][C:23]=3[CH:22]=2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 178452209HCID 178452209, compound

Product 1

HCID 67211599HCID 67211599, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

ClCH2COOEt (1 equiv.) in dimethylforamide was added drop-wise to a solution of 4-(4-oxo-4,5-dihydro-3H-imidazo[4,5-c]pyridin-6-yl)piperazine-1-carboxylic acid tert-butyl ester, 3 and potassium carbonate (0.8 equiv.) in dimethylforamide. The solution was stirred overnight. The mixture was then diluted with water and extracted with methylene chloride. The combined organic layers were dried over magnesium sulfate, and the solvents were evaporated. The product was further purified over a silica column chromatography, eluting with ethyl acetate, to give 4 as a solid.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. customthe solvents were evaporated
  4. customThe product was further purified over a silica column chromatography
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-4bcb1abe17cd444e97cec4f993dd615e
Source dataset
uspto-grants-2012_10
Patent number
US08299023B2

Reaction notes

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