Pyridine → HCID 178454611, compound

HRID 2197505Notes

Reaction equation

HRID 2197505 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][N:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]1[O:17][N:16]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:14]=1.N1C=CC=CC=1.[C:28](Cl)(=[O:32])[CH:29]([CH3:31])[CH3:30]>ClCCl.C(OCC)(=O)C>[OH:12][C:4]1[C:3]([C:13]2[O:17][N:16]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:14]=2)=[C:2]([O:1][C:28](=[O:32])[CH:29]([CH3:31])[CH3:30])[C:11]2[C:6]([N:5]=1)=[N:7][CH:8]=[CH:9][N:10]=2

Participants

6

Reactant 3

HCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 136013426HCID 136013426, compound

Product 1

HCID 178454611HCID 178454611, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-hydroxy-7-(3-trifluoromethyl-isoxazol-5-yl)-5H-pyrido[2,3-b]pyrazin-6-one (Example 6.5) (0.037 g) and pyridine (0.1 ml) in dichloromethane (2 ml) was added dropwise isobutyryl chloride (0.05 ml). The reaction mixture was stirred at ambient temperature for 6 hours and stored at ambient temperature for 16 hours. The reaction mixture was diluted with ethyl acetate, and the organic phase was washed successively with water, aqueous sodium hydrogen carbonate (saturated) and brine. The organic phase was dried over magnesium sulfate and concentrated to give Compound No. B7 of Table B as a pale yellow solid (0.038 g).

Workup

  1. waitstored at ambient temperature for 16 hours
  2. washthe organic phase was washed successively with water, aqueous sodium hydrogen carbonate (saturated) and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give Compound No

Sources & evidence

ORD record
ord-633ff7d33d2c47e289dec133e9e52338
Source dataset
uspto-grants-2012_12
Patent number
US08338598B2

Reaction notes

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