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

HRID 1953418Notes

Reaction equation

HRID 1953418 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.[Br:33][C:34]1[CH:35]=[C:36]([C:40](Cl)=[O:41])[CH:37]=[N:38][CH:39]=1.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[Br:33][C:34]1[CH:35]=[C:36]([C:40]([NH:1][C:2]2[CH:3]=[C:4]([N:8]3[C:13](=[O:14])[C:12]([CH2:15][C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)=[N:11][C:10]4[CH:22]=[CH:23][CH:24]=[N:25][C:9]3=4)[CH:5]=[CH:6][CH:7]=2)=[O:41])[CH:37]=[N:38][CH:39]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 189717365-Bromo-nicotinic acid chloride hydrochlorideHCID 227240264-(3-Aminophenyl)-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine

Product 1

HCID 232981134-[3-[(5-Bromo-3-pyridyl)carbonylamino]phenyl]-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazineYield 54.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(3-aminophenyl)-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (300 mg) and triethylamine (0.33 ml) in 1,4-dioxane (10 ml) was added 5-bromo-3-pyridylcarbonyl chloride·hydrochloride (304 mg). The mixture was stirred at room temperature for 15 minutes, then poured into aqueous sodium bicarbonate and extracted with ethyl acetate. The organic solution was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was crystallized from methanol to give 4-[3-[(5-bromo-3-pyridyl)carbonylamino]phenyl]-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (256 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic solution was washed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-2652db730fca4545861922757fa72006
Source dataset
uspto-grants-2000_09
Patent number
US06117875

Reaction notes

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