Adding a certain compound to certain chemical reactions, such as: 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, belongs to triazoles compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 16681-70-2, Safety of 1H-[1,2,3]Triazole-4-carboxylic acid
Example 20 3-{(R)-3-(5?-Chloro-2?-fluorobiphenyl-4-yl)-2-[(3H-[1,2,3]triazole-4-carbonyl)amino]propyl}tetrahydrofuran-3-carboxylic Acid (isomers a and b) [0453] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)propyl]tetrahydrofuran-3-carboxylic acid (isomer a; 10 mg, 24 mumol, 1.0 eq.) and DIPEA (20 muL, 100 mumol, 4.0 eq.) were dissolved in DMF (100 muL). 1H-1,2,3-triazole-4-carboxylic acid (10 mg, 88 mumol, 3.7 eq.), HATU (15 mg, 39 mumol, 1.6 eq.), and DIPEA (40 muL, 200 mumol, 8.0 eq.) were dissolved in DMF (0.5 mL) and stirred at room temperature for ten minutes, then both solutions were combined and stirred at room temperature and when the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture; the organics were then separated, concentrated and purified by preparative HPLC to yield the title compound (isomer a; 7.8 mg). LCMS (ESI): calc. C23H22ClFN4O4=472; obs. M+H=473.0. Retention time: 4.73 min. [0455] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)propyl]tetrahydrofuran-3-carboxylic acid (isomer b; 10 mg, 24 mumol, 1.0 eq.) and DIPEA (20 muL, 100 mumol, 4.0 eq.) were dissolved in DMF (100 muL). 1H-1,2,3-triazole-4-carboxylic acid (10 mg, 88 mumol, 3.7 eq.), HATU (15 mg, 39 mumol, 1.6 eq.), and DIPEA (40 muL, 200 mumol, 8.0 eq.) were dissolved in DMF (0.5 mL) and stirred at room temperature for ten minutes, then both solutions were combined and stirred at room temperature. When the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture; the organics were then separated, concentrated and purified by preparative HPLC to yield the title compound (isomer b; 2.9 mg). LCMS (ESI): calc. C23H22ClFN4O4=472; obs. M+H=472.9. Retention time: 4.77 min. [0456] LC/MS Method: flow rate: 1.5 mL/min; Buffer A: 0.1% TFA/H2O; Buffer B 0.1% TFA/MeCN; gradient elution from 5-100% B over 9.6 min, then 100% B for 1.0 minute, detection at 254 nm.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-[1,2,3]Triazole-4-carboxylic acid, and friends who are interested can also refer to it.
Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/209352; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics