ETHYL 2-AMINOOXAZOLE-4-CARBOXYLATE Chemical Properties

Melting point:

124-128

Boiling point:

282.9±32.0 °C(Predicted)

Density 

1.278±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

2.82±0.10(Predicted)

form 

solid

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C6H8N2O3/c1-2-10-5(9)4-3-11-6(7)8-4/h3H,2H2,1H3,(H2,7,8)

InChIKey

NBABLVASYFPOEV-UHFFFAOYSA-N

SMILES

O1C=C(C(OCC)=O)N=C1N

CAS DataBase Reference

177760-52-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

Hazard Note 

Harmful/Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

29349990

ETHYL 2-AMINOOXAZOLE-4-CARBOXYLATE Usage And Synthesis

Chemical Properties

Ethyl 2-aminooxazole-4-carboxylate is a carboxylate derivative that can undergo esterification reaction.

Uses

Ethyl 2-aminooxazole-4-carboxylate is an intermediate used in the preparation of inhibitors of Akt activity useful in the treatment of cancer and arthritis.

Synthesis

General procedure for the synthesis of ethyl 2-aminooxazole-4-carboxylate from ethyl 3-bromopyruvate and urea: ethyl 3-bromopyruvate (50.2 g, 257.2 mmol) was dissolved in ethanol and urea (23.2 g, 385.8 mmol) was added with stirring. The reaction mixture was heated to reflux overnight. After completion of the reaction, the solvent was removed by concentration under reduced pressure. The obtained residue was dissolved in a solvent mixture of ethyl acetate and water to separate the organic and aqueous layers. The aqueous layer was extracted with ethyl acetate. All organic layers were combined, washed sequentially with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtration, the organic phase was concentrated under reduced pressure to afford the target product ethyl 2-aminooxazole-4-carboxylate in 85% yield. The structure of the product was confirmed by nuclear magnetic resonance (NMR) and mass spectrometry (MS) analyses.LCMS (ESI+) m/z: 157.1 ([M+H]+).

References

[1] Patent: US2009/23707, 2009, A1. Location in patent: Page/Page column 33-34
[2] Patent: WO2017/17631, 2017, A2. Location in patent: Paragraph 00382
[3] European Journal of Medicinal Chemistry, 2019, p. 80 - 108
[4] Patent: WO2007/146066, 2007, A2. Location in patent: Page/Page column 156-157
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 9, p. 3814 - 3830

ETHYL 2-AMINOOXAZOLE-4-CARBOXYLATE(177760-52-0)Related Product Information

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• ETHYL 2-AMINOOXAZOLE-5-CARBOXYLATE
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• ETHYL 2-MORPHOLINOOXAZOLE-4-CARBOXYLATE
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• ETHYL 2-AMINOOXAZOLE-4-CARBOXYLATE
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• Ethyl 2-amino-1,3-thiazole-4-carboxylate
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