Ethyl Acetate → HCID 22724373, compound

HRID 2231053Notes

Reaction equation

HRID 2231053 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, compoundYield 39.4%

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 mg) 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-f650214928124fe3bd4054621903e250
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

Loading…