4-[[5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL]AMINO]-4-OXO-BUTANOIC ACID Chemical Properties

Density 

1.807±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.17±0.10(Predicted)

Appearance

White to off-white Solid

4-[[5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL]AMINO]-4-OXO-BUTANOIC ACID Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-[[5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl]amino]-4-oxobutanoic acid from succinic anhydride and 5-amino-1,3,4-thiadiazole-2-sulfonamide: To a solution of 5-amino-1,3,4-thiadiazole-2-sulfonamide (0.40 g, 2.22 mmol) in N,N-dimethylformamide was added Succinic anhydride (0.22 g, 2.22 mmol). The reaction mixture was heated at 100 °C with stirring for 12 hours. Upon completion of the reaction, the solvent was removed by rotary evaporator to afford the crude product 4-[[5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl]amino]-4-oxobutanoic acid (0.60 g, 96% yield), which can be used in the next step of the reaction without further purification. The structure of the product was confirmed by the following characterization data: 1H NMR (400 MHz, DMSO-d6) δ 8.33 (s, 2H), 2.78 (t, J = 6.6 Hz, 2H), 2.62 (t, J = 6.4 Hz, 2H); 13C NMR (100 MHz, DMSO-d6) δ 174.08, 172.38, 164.52 , 162.15, 30.77, 29.08; HRMS (ESI+): m/z Calculated value C6H9N4O5S2 [M + H]+: 281.0014, measured value: 281.0009.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 5, p. 915 - 921
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 5077 - 5088
[3] Patent: WO2017/161144, 2017, A1. Location in patent: Page/Page column 69
[4] Patent: US2005/143366, 2005, A1. Location in patent: Page/Page column 18
[5] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 16, p. 4851 - 4856

4-[[5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL]AMINO]-4-OXO-BUTANOIC ACID(78851-85-1)Related Product Information

• 5-BUTYLAMINO-[1,3,4]THIADIAZOLE-2-THIOL
• Propazolamide
• 5-AMINO-1,3,4-THIADIAZOLE-2-SULFONAMIDE
• 2-Acetylamino-5-mercapto-1,3,4-thiadiazole
• 5-(ETHYLAMINO)-1,3,4-THIADIAZOLE-2-THIOL
• 4-[[5-(AMINOSULFONYL)-1,3,4-THIADIAZOL-2-YL]AMINO]-4-OXO-BUTANOIC ACID
• Acetazolamide