Potassium Carbonate → HCID 58114934, compound

HRID 241766Notes

Reaction equation

HRID 241766 reaction equation
CO[C:3]([C:5]1[C:10]([NH:11][C:12](=[O:21])[CH2:13][C:14]2[S:18][C:17]([Cl:19])=[N:16][C:15]=2[CH3:20])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:19][C:17]1[S:18][C:14]([C:13]2[C:12](=[O:21])[NH:11][C:10]3=[N:9][CH:8]=[CH:7][N:6]=[C:5]3[C:3]=2[OH:4])=[C:15]([CH3:20])[N:16]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 581149383-[2-(2-Chloro-4-methyl-thiazol-5-yl)-acetylamino]-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 58114934HCID 58114934, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-[2-(2-Chloro-4-methyl-thiazol-5-yl)-acetylamino]-pyrazine-2-carboxylic acid methyl ester (Example 2.2) (1.020 g) was heated to 110° C. with potassium carbonate (1.08 g) in dry N,N-dimethylformamide (30 ml) for 3 hours. The reaction mixture was allowed to cool to ambient temperature, diluted with water and the mixture extracted with ethyl acetate. The aqueous fraction was acidified to pH 3 by addition of concentrated hydrochloric acid (36% by weight in water) and then extracted again with ethyl acetate. The organic fraction was washed with water, dried over magnesium sulfate, and concentrated to give Compound No. B1 of Table B (0.61 g).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. additionThe aqueous fraction was acidified to pH 3 by addition of concentrated hydrochloric acid (36% by weight in water)
  3. extractionextracted again with ethyl acetate
  4. washThe organic fraction was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give Compound No

Sources & evidence

ORD record
ord-f39db707255b490d9ef1f1a74004dc99
Source dataset
uspto-grants-2014_02
Patent number
US08653078B2

Reaction notes

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