5-Thiazolecarboxylic acid, 4-amino-, methyl ester Chemical Properties

Boiling point:

291℃

Density 

1.408

Flash point:

130℃

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

1.29±0.10(Predicted)

form 

powder

color 

Brown

Safety Information

HS Code 

2934100090

5-Thiazolecarboxylic acid, 4-amino-, methyl ester Usage And Synthesis

Uses

Methyl 4-Aminothiazole-5-carboxylate is used in preparation of Carboxamides as enzyme inhibitors.

Synthesis

General procedure for the synthesis of methyl 4-amino-5-thiazolecarboxylate from methyl 4-amino-2-(methylthio)thiazole-5-carboxylate: methyl 4-amino-2-(methylthio)-1,3-thiazole-5-carboxylate (6.74 g, 33 mmol) was mixed with Raney-Nickel (commercially available slurry, ~15 mL, added in 5 portions) in ethanol (200 mL) in a The suspension was hydrogenated and reacted at 45 psi hydrogen pressure for 1 week. Upon completion of the reaction, the catalyst was removed by filtration and washed with ethyl acetate and ethanol. The filtrate was evaporated to give the crude product. Purification of the crude product by fast column chromatography [eluent: ethyl acetate/isohexane (1:4)] afforded methyl 4-amino-5-thiazolecarboxylate as a bright yellow solid (1.23 g, 24% yield). The product was characterized by NMR (400 MHz, CDCl3): δ 8.54 (1H, s), 5.90 (2H, brs), 3.84 (3H, s). The mass spectrum (ES+) showed a m/z of 159 ([M+H]+).

References

[1] Patent: WO2005/49613, 2005, A1. Location in patent: Page/Page column 42

5-Thiazolecarboxylic acid, 4-amino-, methyl ester(278183-10-1)Related Product Information

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