Sodium Carbonate → 5-Amino-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide

HRID 2244447Notes

Reaction equation

HRID 2244447 reaction equation
C(OC(=O)[NH:7][C:8]1[S:12][C:11]([CH3:13])=[N:10][C:9]=1[C:14](=[O:23])[NH:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([CH3:22])[CH:17]=1)(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>FC(F)(F)C(O)=O>[CH3:22][C:18]1[CH:17]=[C:16]([NH:15][C:14]([C:9]2[N:10]=[C:11]([CH3:13])[S:12][C:8]=2[NH2:7])=[O:23])[CH:21]=[CH:20][N:19]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 68406749Carbamic acid, [2-methyl-4-[[(2-methyl-4-pyridinyl)amino]carbonyl]-5-thiazolyl]-, 1,1-dimethylethyl ester

Product 1

HCID 866065745-Amino-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amideYield 95%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

[2-Methyl-4-(2-methyl-pyridin-4-ylcarbamoyl)-thiazol-5-yl]-carbamic acid tert-butyl ester (0.532 g, 1.53 mmol) was dissolved in 12 mL trifluoroacetic acid and stirred at room temperature for 30 min. The reaction mixture was treated with 2N sodium carbonate solution until pH 10 and extracted three times with ethyl acetate (50 mL each). The organic phases were pooled, dried with sodium sulfate and evaporated. The crude product was flash-chromatographed on silica gel with heptane/ethyl acetate 100:0→0:100 gradient to yield 5-amino-2-methyl-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide as a light yellow solid (0.361 g, 95%), MS (ISP): m/e=249.1 (M+H+).

Workup

  1. extractionextracted three times with ethyl acetate (50 mL each)
  2. dry with materialdried with sodium sulfate
  3. customevaporated
  4. customThe crude product was flash-chromatographed on silica gel with heptane/ethyl acetate 100:0→0:100 gradient

Sources & evidence

ORD record
ord-50c83e0d35d94c479c4d7f57609d0139
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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