Sodium Hydroxide → HCID 68869129, compound

HRID 1986600Notes

Reaction equation

HRID 1986600 reaction equation
[CH3:1][C:2]1[CH2:11][N:10]([CH2:12][CH2:13][CH3:14])[C:9]2[N:8]3[CH2:15][N:16]([OH:18])[CH:17]=[C:7]3[CH:6]=[N:5][C:4]=2[C:3]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21].[OH-].[Na+].Cl[C:27]([F:32])([F:31])C(O)=O>CN(C)C=O>[F:31][CH:27]([F:32])[O:18][N:16]1[CH:17]=[C:7]2[CH:6]=[N:5][C:4]3[C:3]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[C:2]([CH3:1])[CH2:11][N:10]([CH2:12][CH2:13][CH3:14])[C:9]=3[N:8]2[CH2:15]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 66154Chlorodifluoroacetic acidHCID 68870516HCID 68870516, compound

Product 1

HCID 68869129HCID 68869129, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

4.98 g 3-methyl-4-methylsulfonylamino-1-propyl-imidazo[1,5-a]pyrido[3,2-e]pyrazin-8-ol (Example 86) and 1.6 g sodium hydroxide were dissolved in 20 ml dimethylformamide. After 10 min stirring 1.85 ml chlorodifluoroacetic acid was added dropwise. The mixture was heated 5 h at 150° C. bath temperature with stirring. After cooling the product was extracted with ethyl acetate (200 ml, 300 ml), the combined organic phases were washed with water (2×100 ml), the organic phase was dried over sodium sulfate, filtered off, and evaporated to dryness.

Workup

  1. additionwas added dropwise
  2. temperatureAfter cooling the product
  3. extractionwas extracted with ethyl acetate (200 ml, 300 ml)
  4. washthe combined organic phases were washed with water (2×100 ml)
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. filtrationfiltered off
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-d42d9bc57f044b2bb8b88dc2324e7d15
Source dataset
uspto-grants-2009_06
Patent number
US07550465B2

Reaction notes

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