Methyl 2-chloro-3-oxopentanoate → HCID 86592061, compound

HRID 501015Notes

Reaction equation

HRID 501015 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])[C:5]([NH2:8])=[N:6][CH:7]=1.Cl[CH:18]([C:23](=O)[CH2:24][CH3:25])[C:19]([O:21][CH3:22])=[O:20]>>[CH3:22][O:21][C:19]([C:18]1[N:6]2[CH:7]=[C:2]([Cl:1])[N:3]=[C:4]([C:9]3[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=3[Cl:16])[C:5]2=[N:8][C:23]=1[CH2:24][CH3:25])=[O:20]

Participants

3

Reactant 2

HCID 545096Methyl 2-chloro-3-oxopentanoateHCID 22024377HCID 22024377, compound

Product 1

HCID 86592061HCID 86592061, compound

Conditions

Temperature
170 °C

Procedure

5-Chloro-3-(2,4-dichlorophenyl)-2-pyrazineamine (1.1 g, 4.0 mmol) and methyl 2-chloro-3-oxopentanoate (5.7 mL) were mixed, and the mixture was heated under stirring at 170° C. 3 hours. After being allowed to cool, the reaction mixture was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1), and the resulting residue was washed with hexane to give the title compound (0.56 g) as pale yellow crystals.

Workup

  1. temperaturethe mixture was heated
  2. custom3 hours
  3. temperatureto cool
  4. customthe reaction mixture was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)
  5. washthe resulting residue was washed with hexane

Sources & evidence

ORD record
ord-6236ee3366f1454ebce73b614f7b6052
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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