2-((4-(4-Cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid
Lesinurad Impurity B
CAS: 1533519-93-5
Molecular Formula: C17H15N3O2S
2-((4-(4-Cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid - Names and Identifiers
2-((4-(4-Cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid - Physico-chemical Properties
| Molecular Formula | C17H15N3O2S |
| Molar Mass | 325.38 |
| Density | 1.46±0.1 g/cm3(Predicted) |
| Boling Point | 601.0±65.0 °C(Predicted) |
| pKa | 3.05±0.10(Predicted) |
2-((4-(4-Cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid - References
| Background | resynard impurity B is the debromo impurity of resynard, also known as desbromidar. Roxadustat is a hypoxia-inducible factor (HIF) developed by FibroGen and licensed with AstraZeneca small molecule inhibitors of prolyl hydroxylase for the treatment of anemia associated with chronic kidney disease and end-stage renal disease. |
| application | resynard impurity B is a reference in the process of chemical and pharmaceutical research and development, A standard that serves primarily as an impurity control for the manufacturing process of the drug substance resynard. |
| preparation | 1-cyclopropyl-4-isothiocyanate cyanonaphthalene (17.5g) was dissolved in tetrahydrofuran (5ml). Medium. After addition of a solution of hydrazine monohydrate (8.8g) in ethanol (60 ml), the mixture was stirred at 25 °c for 20 minutes, aspirated and the separated product was dried to give 18G (87.5). N-(4-cyclopropylnaphthalen-1-yl) thiosemicarbazide, HPLC purity 98.9. To a solution of N-(4-cyclopropylnaphthalen-1-yl) thiosemicarbazide (21.5g) in tetrahydrofuran was added dimethylformamide-dimethylacetal (20g), after stirring at 25 °c for 3 H, ethyl acetate (80 ml) and brine (50 ml) were added. The isolated product was filtered off and dried to give 19.7g(90%) of 4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2, 4-triazole-3-thiol, HPLC purity 99.5. 5g of NaHCO3 was added to 5.4g of 4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2, 4-triazol-3-thiol in 20ml of DMF. The suspension was stirred. At 25 °c, 5g of bromoacetic acid was added and the mixture was stirred for 3 hours. Then, 20ml of water, 10ml of ethyl acetate, 30ml of 2M hydrochloric acid were added, and the mixture was stirred for 30 minutes. After that, the separated product was filtered and the filter cake was washed with water (2 x 20ml), ethyl acetate (2 x 10ml), ether (2 x 10ml), the product was dried in a vacuum desiccator to give G of resynard impurity B(93%) with a purity of 99.5 (HPLC). |
Last Update：2024-04-09 20:52:54
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