Pyridine → HCID 58114927, compound

HRID 241763Notes

Reaction equation

HRID 241763 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Cl:8][C:9]1[C:14]([C:15]2[C:24](=[O:25])[NH:23][C:18]3=[N:19][CH:20]=[CH:21][N:22]=[C:17]3[C:16]=2[OH:26])=[CH:13][CH:12]=[C:11]([Cl:27])[N:10]=1.N1C=CC=CC=1>ClCCl>[Cl:8][C:9]1[C:14]([C:15]2[C:24](=[O:25])[NH:23][C:18]3=[N:19][CH:20]=[CH:21][N:22]=[C:17]3[C:16]=2[O:26][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[CH:13][CH:12]=[C:11]([Cl:27])[N:10]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 58114915HCID 58114915, compound

Product 1

HCID 58114927HCID 58114927, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pivaloyl chloride (0.096 ml) was added dropwise to a solution of 7-(2,6-dichloro-pyrid-3-yl)-8-hydroxy-5H-pyrido[2,3-b]pyrazin-6-one (Example 1.6) (0.20 g) and pyridine (0.068 ml) in dichloromethane (5 ml) at ambient temperature. The reaction mixture was stirred at ambient temperature for 1 hour and was then diluted with more dichloromethane. The organic phase was washed with aqueous sodium hydrogen carbonate (saturated) and brine, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane 2:1) to give Compound No. A14 of Table A as a white solid (0.088 g).

Workup

  1. washThe organic phase was washed with aqueous sodium hydrogen carbonate (saturated) and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane 2:1)
  5. customto give Compound No

Sources & evidence

ORD record
ord-dcd34a38b4764425aae84522e68a1ea9
Source dataset
uspto-grants-2014_02
Patent number
US08653078B2

Reaction notes

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