Benzoyl chloride → HCID 22724467, compound

HRID 2086843Notes

Reaction equation

HRID 2086843 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:21]=[CH:20][CH:19]=[CH:18][CH:17]=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.[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C>[C:33]([NH:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:14])[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22724309HCID 22724309, compound

Product 1

HCID 22724467HCID 22724467, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-(3-aminophenyl)-3-oxo-2-benzyl-3,4-dihydropyrido[2,3-b]pyrazine (131 mg) and triethylamine (0.067 ml) in dichloromethane (3 ml) was added benzoyl chloride (0.056 ml). The mixture was stirred at room temperature for 30 minutes, then poured into a mixture of ethyl acetate and aqueous sodium bicarbonate solution. The organic phase was separated, washed with brine, dried over magnesium sulfate and concentrated. The residue was crystallized from isopropyl ether to give 4-(3-benzoylaminophenyl)-3-oxo-2-benzyl-3,4-dihydropyrido-[2,3-b]pyrazine (110 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 isopropyl ether

Sources & evidence

ORD record
ord-6864fd46db17451787cc0cbb90fa2c98
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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