Dimethylformamide → HCID 59623738, compound

HRID 1093951Notes

Reaction equation

HRID 1093951 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][S:10]([NH:13][CH2:14][CH2:15][F:16])(=[O:12])=[O:11].CO[C:19]([C:21]1[C:26](Cl)=[N:25][CH:24]=[CH:23][N:22]=1)=O.[C:28](=[O:31])([O-])[O-:29].[K+].[K+].[CH3:34]N(C)C=O.C(O[CH2:43][CH3:44])(=O)C>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:10](=[O:12])(=[O:11])[N:13]([CH2:14][CH2:15][F:16])[C:26]2[C:21]([C:19]=1[O:29][C:28](=[O:31])[CH:43]([CH3:44])[CH3:34])=[N:22][CH:23]=[CH:24][N:25]=2

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1519497Methyl 3-chloropyrazine-2-carboxylateHCID 59623734HCID 59623734, compound

Product 1

HCID 59623738HCID 59623738, compound

Conditions

Temperature
120 °C

Procedure

To C-(2,4-dichloro-phenyl)-N-(2-fluoro-ethyl)-methanesulfonamide (Example 8.1) (0.231 g) was added successively 3-chloro-pyrazine-2-carboxylic acid methyl ester (0.151 g), potassium carbonate (0.446 g) and N,N-dimethylformamide (2 ml). The reaction mixture was heated in a microwave for 25 minutes at 120° C. The reaction mixture was diluted with ethyl acetate and washed with aqueous hydrochloric acid (2M). The organic extracts were dried over magnesium sulfate and concentrated. The residue was dissolved in acetonitrile (1 ml) and 4-dimethylaminopyridine (“DMAP”) (1 mg) and 2,2-dimethylpropionyl chloride (7 μl) were added. The reaction mixture was heated in a microwave at 120° C. for 25 minutes. The reaction mixture was concentrated and the residue purified by column chromatography on silica gel (eluent: ethyl acetate/hexane 15:85) to give Compound No. C58 of Table C (21 mg).

Workup

  1. washwashed with aqueous hydrochloric acid (2M)
  2. dry with materialThe organic extracts were dried over magnesium sulfate
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in acetonitrile (1 ml)
  5. addition4-dimethylaminopyridine (“DMAP”) (1 mg) and 2,2-dimethylpropionyl chloride (7 μl) were added
  6. temperatureThe reaction mixture was heated in a microwave at 120° C. for 25 minutes
  7. concentrationThe reaction mixture was concentrated
  8. customthe residue purified by column chromatography on silica gel (eluent: ethyl acetate/hexane 15:85)
  9. customto give Compound No

Sources & evidence

ORD record
ord-0e63f38c8fe84334bf26337a14989259
Source dataset
uspto-grants-2012_03
Patent number
US08133849B2

Reaction notes

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