Methyl iodide → HCID 58114936, compound

HRID 241768Notes

Reaction equation

HRID 241768 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:8]2[C:17](=[O:18])[NH:16][C:11]3=[N:12][CH:13]=[CH:14][N:15]=[C:10]3[C:9]=2[O:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])=[C:5]([CH3:7])[N:6]=1.CI.[C:27](=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[S:3][C:4]([C:8]2[C:17](=[O:18])[N:16]([CH3:27])[C:11]3=[N:12][CH:13]=[CH:14][N:15]=[C:10]3[C:9]=2[O:19][C:20](=[O:24])[CH:21]([CH3:22])[CH3:23])=[C:5]([CH3:7])[N:6]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58114926Isobutyric acid 7-(2-chloro-4-methyl-thiazol-5-yl)-6-oxo-5,6-dihydro-pyrido[2,3-b]pyrazin-8-yl ester

Product 1

HCID 58114936HCID 58114936, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Isobutyric acid 7-(2-chloro-4-methyl-thiazol-5-yl)-6-oxo-5,6-dihydro-pyrido[2,3-b]pyrazin-8-yl ester (Example 2.4) (0.10 g), methyl iodide (0.18 ml) and potassium carbonate (0.075 g) were heated in acetonitrile (4 ml) in a microwave to 100° C. for 10 minutes. The reaction mixture was allowed to cool to ambient temperature and then diluted with ethyl acetate and water. The phases were separated and the organic phase was washed with water, aqueous sodium hydrogen carbonate (saturated) and brine, dried over magnesium sulfate and concentrated to give Compound No. B2 of Table B (0.078 g).

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with water, aqueous sodium hydrogen carbonate (saturated) and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give Compound No

Sources & evidence

ORD record
ord-d231bd5d87734108a45614a913a2dfae
Source dataset
uspto-grants-2014_02
Patent number
US08653078B2

Reaction notes

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