Potassium Carbonate → HCID 15487472, compound

HRID 1953460Notes

Reaction equation

HRID 1953460 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[C:9](=[O:27])[N:10]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:11]([CH3:20])=[CH:12][C:13]=1[S:14]([CH2:17][CH2:18]Cl)(=[O:16])=[O:15]>CC(N(C)C)=O>[CH2:25]([O:24][C:22]([CH2:21][N:10]1[C:11]([CH3:20])=[CH:12][C:13]2[S:14](=[O:16])(=[O:15])[CH2:17][CH2:18][NH:7][C:8]=2[C:9]1=[O:27])=[O:23])[CH3:26]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 23298248HCID 23298248, compound

Product 1

HCID 15487472HCID 15487472, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of potassium carbonate (45 mg) and 3-amino-4-(2-chloroethylsulfonyl)-1-ethyloxycarbonylmethyl-6-methyl-2-pyridinone (120 mg, 0.33 mmol) in dimethyl acetamide (1.0 mL) was stirred at 160° C. for 1 h. The reaction mixture was cooled and partitioned between ethyl acetate and dilute HCl. The organic layer was washed with brine, dried (Na2SO4) and evaporated to a semi-solid. The crude product was purified by flash column chromatography on silica gel (70-100% ethyl acetate/hexanes gradient) to give the title compound as a colorless crystalline solid:

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl acetate and dilute HCl
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to a semi-solid
  6. customThe crude product was purified by flash column chromatography on silica gel (70-100% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-bffc34692ad94e29b5562147e3bbe6ea
Source dataset
uspto-grants-2000_09
Patent number
US06117888

Reaction notes

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