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| | 4-[[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]amino]-4-oxo-butanoic acid Basic information |
| Product Name: | 4-[[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]amino]-4-oxo-butanoic acid | | Synonyms: | 2-succinylamido-1,3,4-thiadiazole-5-sulfonamide;4-Oxo-4-((5-sulfamoyl-1,3,4-thiadiazol-2-yl);Butanoic acid, 4-[[5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl]amino]-4-oxo-;4-Oxo-4-((5-sulfamoyl-1,3,4-thiadiazol-2-yl)amino)butanoic acid;4-[[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]amino]-4-oxo-butanoic acid | | CAS: | 78851-85-1 | | MF: | C6H8N4O5S2 | | MW: | 280.28 | | EINECS: | | | Product Categories: | | | Mol File: | 78851-85-1.mol | ![4-[[5-(Aminosulfonyl)-1,3,4-thiadiazol-2-yl]amino]-4-oxo-butanoic acid Structure](CAS/GIF/78851-85-1.gif) |
| | 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 Preparation Products And Raw materials |
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