Ethyl Acetate → HCID 22724373, compound

HRID 2086877Notes

Reaction equation

HRID 2086877 reaction equation
C([O:4][C:5]1[CH:37]=[CH:36][C:8]([C:9]([NH:11][C:12]2[CH:13]=[C:14]([N:18]3[C:23](=[O:24])[C:22]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[N:21][C:20]4[CH:32]=[CH:33][CH:34]=[N:35][C:19]3=4)[CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CO.O1CCOCC1.O>[CH2:25]([C:22]1[C:23](=[O:24])[N:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([NH:11][C:9](=[O:10])[C:8]3[CH:36]=[CH:37][C:5]([OH:4])=[CH:6][CH:7]=3)[CH:13]=2)[C:19]2[N:35]=[CH:34][CH:33]=[CH:32][C:20]=2[N:21]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 22724047HCID 22724047, compound

Product 1

HCID 22724373HCID 22724373, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 4-[3-(4-acetoxybenzoylamino)phenyl]-2-benzyl-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (147 ma) in methanol (3 ml) and 1,4-dioxane (3 ml) was added a solution of potassium carbonate (83 mg) in water (0.5 ml). The mixture was stirred at room temperature for 1.5 hours, then poured into a mixture of ethyl acetate and water. The organic phase was separated, washed with brine, dried over magnesium sulfate and concentrated. The residue was crystallized from ethanol to give 2-benzyl-4-[3-(4-hydroxybenzoylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (53 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-e2a86b1624a9438ca691b01847bc95d5
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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