Ethyl 2-chloroacetoacetate → HCID 86717940, compound

HRID 1624121Notes

Reaction equation

HRID 1624121 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([NH2:13])=[N:8][CH:9]=[CH:10][C:11]=1[F:12].Cl[CH:20]([C:26]([CH3:28])=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(O)C>[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:26]([CH3:28])[N:13]=2)[CH:9]=[CH:10][C:11]=1[F:12]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 86717939HCID 86717939, compound

Product 1

HCID 86717940HCID 86717940, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under argon, 500 mg (1.97 mmol) of 3-[(2,6-difluorobenzyl)oxy]-4-fluoropyridine-2-amine Example 110A were initially charged in 10 ml of ethanol, and 500 mg of powdered molecular sieve 4 Å and 3.24 g (19.67 mmol) of ethyl 2-chloroacetoacetate were added. The resulting reaction mixture was heated at reflux for 48 h. All volatile components were substantially evaporated on a dry ice rotary evaporator at a water bath temperature of 85° C. The crude product was purified by silica gel chromatography (mobile phase: cyclohexane/ethyl acetate=9/1 isocratic). This gave 368 mg (39% of theory; purity about 76%) of the title compound.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 48 h
  4. customAll volatile components were substantially evaporated on a dry ice rotary evaporator at a water bath temperature of 85° C
  5. customThe crude product was purified by silica gel chromatography (mobile phase: cyclohexane/ethyl acetate=9/1 isocratic)

Sources & evidence

ORD record
ord-1f63256e08684c1299cd799bf7230d2e
Source dataset
uspto-grants-2014_07
Patent number
US08778964B2

Reaction notes

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