3,5-Dichlorobenzoyl chloride → 4-[3-(3,5-Dichlorobenzoylamino)phenyl]-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazinehydrochloride

HRID 2086855Notes

Reaction equation

HRID 2086855 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.[Cl:26][C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([Cl:36])[CH:35]=1)[C:30](Cl)=[O:31]>C(Cl)(Cl)Cl>[ClH:26].[Cl:26][C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([Cl:36])[CH:35]=1)[C:30]([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:31]

Participants

4

Reactant 2

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

Product 1

HCID 227241864-[3-(3,5-Dichlorobenzoylamino)phenyl]-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazinehydrochlorideYield 130.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-(3-aminophenyl)-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (329 mg) in chloroform (5 ml) was added 3,5-dichlorobenzoylchloride (220 mg). The mixture was stirred at room temperature for 15 minutes and concentrated. The residue was crystallized from methanol to give 4-[3-(3,5-dichlorobenzoylamino)phenyl]-2-(3-pyridylmethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine.hydrochloride (370 mg).

Workup

  1. concentrationconcentrated
  2. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-c3979eaee8384ec9908f34f9685c2cc9
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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