Carbamic acid, N-(4-bromo-2-thiazolyl)-, 1,1-dimethylethyl ester Chemical Properties

Density 

1.574±0.06 g/cm3(Predicted)

storage temp. 

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

pka

4.58±0.70(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C8H11BrN2O2S/c1-8(2,3)13-7(12)11-6-10-5(9)4-14-6/h4H,1-3H3,(H,10,11,12)

InChIKey

OVRIFGLINJVMLO-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NC1=NC(Br)=CS1

Carbamic acid, N-(4-bromo-2-thiazolyl)-, 1,1-dimethylethyl ester Usage And Synthesis

Synthesis

General procedure for the synthesis of tert-butyl 4-bromothiazole-2-methylamine from N-BOC-2-amino-5-bromothiazole: diisopropylamine (2.3 mL, 16 mmol) was dissolved in 30 mL of THF at 0 °C. To this solution, 2.5 M hexane solution of butyl lithium (6.4 mL, 16 mmol) was slowly added and the reaction mixture was stirred at the same temperature for 20 min. Subsequently, tert-butyl 5-bromothiazol-2-ylcarbamate (1.5 g, 5.4 mmol) was dissolved in 8 mL of THF and slowly added dropwise to the reaction system. After 15 minutes of reaction, the reaction was quenched by the addition of about 2 mL of water and the mixture was gradually warmed to room temperature with continued stirring for 12 hours. Upon completion of the reaction, the reaction mixture was diluted with 30 mL of 1/2 saturated aqueous NH4Cl and transferred to a dispensing funnel. It was extracted twice with 5 mL EtOAc, and the organic phases were combined, washed with brine and dried over MgSO4. After filtration, the organic phase was concentrated under reduced pressure to give tert-butyl 4-bromothiazol-2-ylcarbamate (1.5 g, 100% yield) as a brown solid.

References

[1] Patent: US2007/173506, 2007, A1. Location in patent: Page/Page column 61; 62
[2] Patent: WO2010/83246, 2010, A1. Location in patent: Page/Page column 123
[3] Patent: US2009/36467, 2009, A1. Location in patent: Page/Page column 64; 72; 73
[4] Patent: US2012/108591, 2012, A1. Location in patent: Page/Page column 29
[5] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 896 - 916

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