Application of 4928-87-4,Some common heterocyclic compound, 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, molecular formula is C3H3N3O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Example 1: N-[2-[[4-[(lR,3S)-3-[[( lR)-l-(4-Fluoro-3-methoxy-phenyl) ethyl]-amino]cyclopentyl]benzoyl]amino]ethyl]-lH-l,2,4-triazole-3- carboxamide (Compound 101)To a solution of Intermediate 4 (719 mg, 1.8 mmol) in dry DMF (12 mL) was added HOBt (276 mg, 2 mmol) and EDAC (517 mg, 2.7 mmol), and the mixture was stirred at rt for 4 hours. lH-l,2,4-triazole-3-carboxylic acid (200 mg, 1.8 mmol) was then added, and stirring was continued overnight at rt. The solvent was removed under reduced pressure and the crude purified by flash chromatography (30% MeOH/DCM), affording the title compound in 78% yield. *H NMR (300 MHz, DMSO) delta 8.70 (br m, IH), 8.48 (br m, IH), 8.41 (s, IH), 7.76 (d, J = 8.2 Hz, 2H), 7.31 (d, J = 8.2 Hz, 2H), 7.17 (dd, J = 8.6, 1.6 Hz, IH), 7.10 (dd, J = 11.5, 8.3 Hz, IH), 6.89 (ddd, J = 8.1, 4.4, 1.8 Hz, IH), 3.84 (s, 3H), 3.78 (q, J = 6.6 Hz, IH), 3.46 (br m, 4H), 3.04 – 2.85 (m, 2H), 2.15 – 1.54 (m, 6H), 1.43 – 1.19 (m, 4H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2,4-Triazole-3-carboxylic acid, its application will become more common.
Reference:
Patent; LEO PHARMA A/S; MANSSON, Kristoffer; WO2012/69421; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics