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| | 4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoicacid Basic information |
| | 4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoicacid Chemical Properties |
| Melting point | 169-171℃ | | Boiling point | 346℃ | | density | 1.518 | | Fp | 163℃ | | storage temp. | 2-8°C | | solubility | DMSO | | form | Solid | | pka | 3.26±0.10(Predicted) | | color | Off-White | | InChI | InChI=1S/C10H5F3N2O3/c11-10(12,13)9-14-7(15-18-9)5-1-3-6(4-2-5)8(16)17/h1-4H,(H,16,17) | | InChIKey | WJQLFPSEXHEXRM-UHFFFAOYSA-N | | SMILES | C(O)(=O)C1=CC=C(C2N=C(C(F)(F)F)ON=2)C=C1 |
| | 4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoicacid Usage And Synthesis |
| Uses | 4-(5-Trifluoromethyl-1,2,4-oxadiazol-3-yl)-benzoic Acid is an intermediate in the synthesis of small molecule inhibitors of HIV-1 gp41. | | Synthesis | General procedure for the synthesis of 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoic acid from trifluoroacetic anhydride and 4-[(Z)-amino(hydroxyiminomethyl)methyl]benzoic acid: a solution of tetrahydrofuran (2.5 L) of 4-[(Z)-N'-hydroxyformamidinyl]benzoic acid (200 g, 1.0 equiv) was treated with trifluoroacetic anhydride (350 g, 1.5 equivalent) treatment. The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was diluted with methyl tert-butyl ether and washed with saturated aqueous sodium bicarbonate. The organic layer was separated and concentrated under reduced pressure to remove the solvent to give the crude product. The crude product was purified by recrystallization from diisopropyl ether to afford 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoic acid as a light brown solid (220 g, 76% yield).1H NMR (400 MHz, DMSO-d6, 298 K): δ [ppm] = 13.40 (broad single peak, 1H), 8.22-8.10 (multiple peaks 4H). | | References | [1] Patent: WO2017/76739, 2017, A1. Location in patent: Page/Page column 100
[2] Patent: WO2017/93019, 2017, A1. Location in patent: Page/Page column 66
[3] Patent: WO2017/211650, 2017, A1. Location in patent: Page/Page column 28
[4] Patent: WO2017/211652, 2017, A1. Location in patent: Page/Page column 19
[5] Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 7843 - 7854 |
| | 4-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoicacid Preparation Products And Raw materials |
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