Chloroacetyl chloride → HCID 22034146, compound

HRID 1792275Notes

Reaction equation

HRID 1792275 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2=[N:14][C:15]([CH3:19])=[CH:16][C:17]([NH2:18])=[C:12]2[N:11]=[C:10]1[CH3:20].C(N(CC)C(C)C)(C)C.[Cl:30][CH2:31][C:32](Cl)=[O:33].C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2=[N:14][C:15]([CH3:19])=[CH:16][C:17]([NH:18][C:32](=[O:33])[CH2:31][Cl:30])=[C:12]2[N:11]=[C:10]1[CH3:20]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 22034107HCID 22034107, compound

Product 1

HCID 22034146HCID 22034146, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Treat a solution of 3-(2,4-dichlorophenyl)-2,5-dimethylimidazolo[5,4-b]pyridin-7-ylamine (0.2 g, 0.65 mmol), and N,N-diisopropylethylamine, (0.12 mL, 0.72 mmol) in 1,2-dichloroethane (10 mL) with chloroacetyl chloride (0.06 mL, 30.72 mmol). Heat the solution to reflux for 2 h, cool to ambient temperature, and pour into an aqueous potassium carbonate solution. Extract the resulting mixture with CH2Cl2 and wash with saturated aq NaCl. Separate the organic layer, dry over Na2SO4, filter, and concentrate. Purify by preparative TLC (5% methanol in CH2Cl2) to obtain the title compound as a yellow solid.

Workup

  1. temperatureHeat the solution
  2. temperatureto reflux for 2 h
  3. extractionExtract the resulting mixture with CH2Cl2
  4. washwash with saturated aq NaCl
  5. customSeparate the organic layer
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify by preparative TLC (5% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-fdfd86257a8f43f7bfd2fa8ca41ff73e
Source dataset
uspto-grants-2006_07
Patent number
US07074929B2

Reaction notes

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