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

HRID 2244456Notes

Reaction equation

HRID 2244456 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 68406749[2-Methyl-4-(2-methyl-pyridin-4-ylcarbamoyl)-thiazol-5-yl]-carbamic acid tert-butyl 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-58679bfc73dc473e8a7a30518ec6adb8
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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