Triethylamine → 4-[3-(3,5-Dichlorobenzoylamino)phenyl]-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine

HRID 2231029Notes

Reaction equation

HRID 2231029 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:14])[C:12]([CH2:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[N:11][C:10]3[CH:22]=[CH:23][CH:24]=[N:25][C:9]2=3)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[Cl:33][C:34]1[CH:35]=[C:36]([CH:40]=[C:41]([Cl:43])[CH:42]=1)[C:37](Cl)=[O:38].C(=O)(O)[O-].[Na+]>O1CCOCC1.C(OCC)(=O)C>[Cl:33][C:34]1[CH:35]=[C:36]([CH:40]=[C:41]([Cl:43])[CH:42]=1)[C:37]([NH:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:14])[C:12]([CH2:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[N:11][C:10]3[CH:22]=[CH:23][CH:24]=[N:25][C:9]2=3)[CH:5]=[CH:6][CH:7]=1)=[O:38]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 761913,5-Dichlorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 227240264-(3-Aminophenyl)-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine

Product 1

HCID 98516064-[3-(3,5-Dichlorobenzoylamino)phenyl]-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazineYield 59.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 4-(3-aminophenyl)-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (180 mg) and triethylamine (0.10 ml) in 1,4-dioxane (4 ml) was added 3,5-dichlorobenzoylchloride (126 mg). The mixture was stirred at room temperature for 10 minutes, then poured into a mixture of ethyl acetate and aqueous sodium bicarbonate. The organic phase was separated, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column (ethyl acetate) and crystallized from ethanol to give 4-[3-(3,5-dichlorobenzoylamino)phenyl]-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (163 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel column (ethyl acetate)
  6. customcrystallized from ethanol

Sources & evidence

ORD record
ord-04e9b28840564c08b7e6261a20ebd8db
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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