Reference of 16681-70-2, New Advances in Chemical Research in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.
Example 41 (S)-N-(2-(2-cyanopyrrolidine-1-yl)-2-oxoethyl)-1H-1,2,3-triazole-5-carboxamide 1H-1,2,3-triazole-4-carboxylic acid (0.092 g, 0.814 mmol) was dispersed in dry dioxane (3 mL) in a round bottom flask with nitrogen. To this 1-chloro-N,N,2-trimethylprop-1-en-1-amine (0.151 ml, 1.139 mmol) was added and the reaction was stirred for 30 minutes at room temperature. The starting material dissolves over time. Then (S)-1-(2-aminoacetyl)pyrrolidine-2-carbonitrile hydrochloride (0.247 g, 1.302 mmol) with N-ethyl-N-isopropylpropan-2-amine (0.307 ml, 1.709 mmol) was added and the mixture was stirred for 2 h, evaporated to dryness and redissolved in ethyl acetate. Followed by washing with 0.1N citric acid and saturated sodium bicarbonate and brine. After drying over sodium sulfate, filtration and evaporation, the product was purified using column chromatography. Yield: 34 mg, 40% 1H NMR (400 MHz, DMSO) (9/1 mixture of trans/cis amide rotamers) delta 15.53 (s, 1H), 8.58-8.44 (s, 1H), 8.39 (s, 1H), 5.28-5.22 (m, 0.1H), 4.77 (dd, J=3.76, 7.32 Hz, 1H), 4.30 (dd, J=5.61, 16.77 Hz, 0.2H), 4.10 (d, J=5.76 Hz, 2H), 3.68 (ddd, J=4.04, 7.68, 9.39 Hz, 1H), 3.50 (td, J=6.84, 9.09 Hz, 1H), 2.31-1.88 (m, 4H). UPLC I (ESI) Rt 0.72 min, m/z 249.6 [M+H]+ (96%); LC-MS (I-B) Rt 4.0 min, m/z 249.0 [M+H]+ (96%)
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Reference:
Patent; Fox Chase Cancer Center; Jansen, Koen; De Meester, Ingrid; Heirbaut, Leen; Cheng, Jonathan D.; Joossens, Jurgen; Augustyns, Koen; Van Der Veken, Pieter; US2014/357650; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics