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

HRID 2230973Notes

Reaction equation

HRID 2230973 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=2)[C:5]2[N:16]=[CH:17][CH:18]=[CH:19][C:4]=2[N:3]=1.C(N(CC)CC)C.[Cl:27][C:28]1[CH:29]=[C:30]([CH:34]=[C:35]([Cl:37])[CH:36]=1)[C:31](Cl)=[O:32]>O1CCOCC1>[CH3:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:31](=[O:32])[C:30]3[CH:29]=[C:28]([Cl:27])[CH:36]=[C:35]([Cl:37])[CH:34]=3)[CH:10]=2)[C:5]2[N:16]=[CH:17][CH:18]=[CH:19][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 761913,5-Dichlorobenzoyl chlorideHCID 227239942-Methyl-4-(3-aminophenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine

Product 1

HCID 227243002-Methyl-4-[3-(3,5-dichlorobenzoylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazineYield 35.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-methyl-4-(3-aminophenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (7.4 g) and triethylamine (5.72 ml) in dioxane was added 3,5-dichlorobenzoyl chloride (6.14 g) in dropwise. The mixture was stirred for 3 hours at room temperature. The reaction mixture was quenched by water and extracted with ethyl acetate (100 ml). The crude product was purified by chromatography to obtain 2-methyl-4-[3-(3,5-dichlorobenzoylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (4.4 g).

Workup

  1. customThe reaction mixture was quenched by water
  2. extractionextracted with ethyl acetate (100 ml)
  3. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-f285021b34f14a739f11d0db6e0561d0
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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