Methyl iodide → HCID 58114936, compound

HRID 2197493Notes

Reaction equation

HRID 2197493 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-74d8d1ac97b04c9db33a63a374f79fdf
Source dataset
uspto-grants-2012_12
Patent number
US08338598B2

Reaction notes

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