Aniline → HCID 22724334, compound

HRID 2086848Notes

Reaction equation

HRID 2086848 reaction equation
[CH2:1]([C:8]1[C:13](=[O:14])[N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17](C(O)=O)[CH:16]=2)[C:11]2[N:24]=[CH:25][CH:26]=[CH:27][C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[C:47](=[O:50])(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([C:8]1[C:13](=[O:14])[N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:47]([NH:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:50])[CH:16]=2)[C:11]2[N:24]=[CH:25][CH:26]=[CH:27][C:10]=2[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 22724010HCID 22724010, compound

Product 1

HCID 22724334HCID 22724334, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-benzyl-3-oxo-4-(3-carboxyphenyl)-3,4-dihydropyrido[2,3-b]pyrazine (186 mg) and 1,1′-carbonyldiimidazole (130 mg) in tetrahydrofuran (4 ml) was stirred at room temperature for 3 hours. Aniline (0.075 ml) was then added to the mixture and stirring was continued for 24 hours. The reaction mixture was poured into a mixture of ethyl acetate and aqueous sodium bicarbonate solution. The organic phase was washed with brine, dried over magnesium sulfate, concentrated, and subjected to silica gel column chromatography (chloroform-methanol, 40:1) to afford 2-benzyl-3-oxo-4-(3-anilinocarbonylphenyl)-3,4-dihydropyrido[2,3-b]pyrazine (103 mg) as a solid.

Workup

  1. stirringstirring
  2. waitwas continued for 24 hours
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-821201ea7f794e0a90e61f663226a121
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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