Quinaldic Acid → HCID 22724513, compound

HRID 2086849Notes

Reaction equation

HRID 2086849 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:26][C:27]1[CH:28]=[C:29]([N:33]2[C:38](=[O:39])[C:37]([CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[N:36][C:35]3[CH:47]=[CH:48][CH:49]=[N:50][C:34]2=3)[CH:30]=[CH:31][CH:32]=1.C(=O)(O)[O-].[Na+]>O1CCCC1.O1CCOCC1.C(OCC)(=O)C>[CH2:40]([C:37]1[C:38](=[O:39])[N:33]([C:29]2[CH:30]=[CH:31][CH:32]=[C:27]([NH:26][C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)=[O:13])[CH:28]=2)[C:34]2[N:50]=[CH:49][CH:48]=[CH:47][C:35]=2[N:36]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

8

Reactant 4

HCID 7124Quinaldic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 22724309HCID 22724309, compound

Product 1

HCID 22724513HCID 22724513, compoundYield 12%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-quinolinecarboxylic acid (520 mg) and 1,1′-carbonyldiimidazole (243 mg) in tetrahydrofuran (5 ml) was stirred at room temperature for 1.5 hours. A solution of 4-(3-aminophenyl)-3-oxo-2-benzyl-3,4-dihydropyrido[2,3-b]pyrazine (493 mg) in 1,4-dioxane (5 ml) was added to the mixture and stirring was continued for 5 days. The reaction mixture was poured into a mixture of ethyl acetate and an aqueous sodium bicarbonate solution. The organic phase was washed with brine, dried over magnesium sulfate, concentrated, and subjected to silica gel column chromatography (hexane-ethyl acetate, 1:1) to afford 2-benzyl-3-oxo-4-[3-(quinolin-2-yl)carbonylaminophenyl]-3,4-dihydropyrido[2,3-b]pyrazine (87 mg) as a solid.

Workup

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

Sources & evidence

ORD record
ord-ed77f7ac88fd42ecb5a82aed6d858fc8
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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