Water → HCID 58114921, compound

HRID 241760Notes

Reaction equation

HRID 241760 reaction equation
[Cl:1][C:2]1[C:3]([C:9]2[C:18]([OH:19])=[N:17][C:12]3=[N:13][CH:14]=[CH:15][N:16]=[C:11]3[C:10]=2[OH:20])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.N1C=CC=CC=1.[C:27](Cl)(=[O:31])[CH:28]([CH3:30])[CH3:29].O>ClCCl>[Cl:1][C:2]1[C:3]([C:9]2[C:18](=[O:19])[NH:17][C:12]3=[N:13][CH:14]=[CH:15][N:16]=[C:11]3[C:10]=2[O:20][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 178517382HCID 178517382, compound

Product 1

HCID 58114921HCID 58114921, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-(3,5-Dichloro-pyrid-2-yl)-pyrido[2,3-b]pyrazine-6,8-diol (Example 1.2) (1.6 g) was dissolved in dichloromethane (50 ml) containing pyridine (0.445 g) and the reaction mixture stirred for 10 minutes. Isobutyryl chloride (0.556 g) was added dropwise over 5 minutes and the reaction mixture stirred for two hours. Water was added and the mixture extracted with ethyl acetate. The phases were separated and the organic fraction was washed with aqueous sodium carbonate (1M). The organic fraction was dried over sodium sulfate and concentrated to give a pale yellow solid which was recrystallized from ethyl acetate/hexane to give Compound No. A5 of Table A (1.02 g).

Workup

  1. stirringthe reaction mixture stirred for two hours
  2. extractionthe mixture extracted with ethyl acetate
  3. customThe phases were separated
  4. washthe organic fraction was washed with aqueous sodium carbonate (1M)
  5. dry with materialThe organic fraction was dried over sodium sulfate
  6. concentrationconcentrated
  7. customto give a pale yellow solid which
  8. customwas recrystallized from ethyl acetate/hexane
  9. customto give Compound No

Sources & evidence

ORD record
ord-7a5b40c3963a464e9038db223023ee12
Source dataset
uspto-grants-2014_02
Patent number
US08653078B2

Reaction notes

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