P-Anisidine → HCID 131720765, compound

HRID 1956435Notes

Reaction equation

HRID 1956435 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([O:12][CH2:13][CH3:14])=[CH:9][N:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[CH3:20][O:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1>C(O)C>[OH2:12].[ClH:1].[CH2:13]([O:12][C:8]1[N:7]=[C:6]2[N:5]=[CH:4][C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:2]([NH:26][C:25]3[CH:27]=[CH:28][C:22]([O:21][CH3:20])=[CH:23][CH:24]=3)[C:11]2=[N:10][CH:9]=1)[CH3:14].[ClH:1].[ClH:1].[CH2:18]([O:17][C:15]([C:3]1[CH:4]=[N:5][C:6]2=[N:7][C:8]([O:12][CH2:13][CH3:14])=[CH:9][N:10]=[C:11]2[C:2]=1[NH:26][C:25]1[CH:27]=[CH:28][C:22]([O:21][CH3:20])=[CH:23][CH:24]=1)=[O:16])[CH3:19].[OH2:12]

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 23209231HCID 23209231, compound

Product 1

HCID 131720765HCID 131720765, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 8-chloro-3-ethoxypyrido[2,3-b]-pyrazine-7-carboxylate (2.32 g) and 4-methoxyaniline (1.0 g) in ethanol (40 ml) was boiled under reflux for 1 hour. The mixture was allowed to cool and the solvent removed under reduced pressure. The residue was triturated with hot ethyl acetate and filtered to give a solid which was recrystallised from ethyl acetate to give a solid which was purified by chromatography on silica to give ethyl 3-ethoxy-8-(4-methoxyanilino)pyrido[2,3-b]pyrazine-7-carboxylate sesquihydrochloride hydrate, m.p. 143°-145° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureto cool
  3. customthe solvent removed under reduced pressure
  4. customThe residue was triturated with hot ethyl acetate
  5. filtrationfiltered
  6. customto give a solid which
  7. customwas recrystallised from ethyl acetate
  8. customto give a solid which
  9. customwas purified by chromatography on silica

Sources & evidence

ORD record
ord-3d09b650cc674d1182b47bb1ceaf66bd
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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