Potassium Carbonate → 5-(4-Fluoro-phenyl)-2-methyl-thiazole-4-carboxylic Acid (2-amino-ethyl)-methyl-amide

HRID 2376693Notes

Reaction equation

HRID 2376693 reaction equation
[CH3:1][N:2]([CH2:18][CH2:19][NH:20]C(=O)C(F)(F)F)[C:3]([C:5]1[N:6]=[C:7]([CH3:17])[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=[O:4].C([O-])([O-])=O.[K+].[K+]>CO.O>[NH2:20][CH2:19][CH2:18][N:2]([CH3:1])[C:3]([C:5]1[N:6]=[C:7]([CH3:17])[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=[O:4]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 865997195-(4-Fluoro-phenyl)-2-methyl-thiazole-4-carboxylic Acid Methyl-[2-(2,2,2-trifluoro-ethanoylamino)-ethyl]-amide

Product 1

HCID 687275705-(4-Fluoro-phenyl)-2-methyl-thiazole-4-carboxylic Acid (2-amino-ethyl)-methyl-amideYield 72%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 5-(4-fluoro-phenyl)-2-methyl-thiazole-4-carboxylic acid methyl-[2-(2,2,2-trifluoro-ethanoylamino)-ethyl]-amide, D4 (443 mg, 1.14 mmol) im methanol/water (30 ml/10 ml) was treated with solid K2CO3 (787 mg, 5.70 mmol) and stirred at room temperature, under argon for 16 h. The methanol was removed in vacuo. The residue was diluted with water and extracted with ethyl acetate (3×). The combined organics were dried (MgSO4) and the solvent removed in vacuo to afford the title compound as a yellow gum (240 mg, 72%).

Workup

  1. customThe methanol was removed in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialThe combined organics were dried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-7d0528f2345e444098e5d2d291b22523
Source dataset
uspto-grants-2008_12
Patent number
US07468367B2

Reaction notes

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