16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, belongs to Triazoles compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C3H3N3O2
Example 16 (R)-5-(5?-Chloro-2?-fluorobiphenyl-4-yl)-2-(2-hydroxyethyl)-2-hydroxymethyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic Acid (isomers a and b) [0438] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)-propyl]-3-hydroxymethyl-dihydro-furan-2-one (isomer a; 10 mg, 30 mumol, 1.0 eq.) and DIPEA (30 muL, 170 mumol, 5.6 eq.) were dissolved in DMF (200 muL). 1H-1,2,3-triazole-4-carboxylic acid (10 mg, 90 mumol, 3.0 eq.), DIPEA (60 muL, 340 mumol, 11.2 eq.) and HATU (15 mg, 40 mumol, 1.3 eq.), were dissolved in DMF (600 muL) and stirred at room temperature for a few minutes. The solutions were then combined and the resulting mixture 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 and concentrated in vacuo. The crude residue was dissolved in a 1:1 solution of MeOH and aqueous 2N NaOH (4 mL), and stirred at room temperature for 30 minutes and when the reaction was complete (as determined by LC/MS analysis), the mixture was concentrated in vacuo and purified by preparative HPLC to yield the title compound (isomer a; 3 mg). LCMS (ESI): calc. C23H24ClFN4O5=490; obs. M+H=491.2. Retention time: 2.04 min. [0440] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)-propyl]-3-hydroxymethyl-dihydro-furan-2-one (isomer b; 30 mg, 52 mumol, 1.0 eq.) and DIPEA (50 muL, 291 mumol, 5.6 eq.) were dissolved in DMF (200 muL). 1H-1,2,3-triazole-4-carboxylic acid (17 mg, 156 mumol, 3.0 eq.), DIPEA (100 muL, 582 mumol, 11.2 equiv.) and HATU (25 mg, 68 mumol, 1.3 eq.), were dissolved in DMF (600 muL) and stirred at room temperature for a few minutes. The solutions were then combined and the resulting mixture was stirred at room temperature; when the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture. The organic layer was separated, concentrated in vacuo and purified by preparative HPLC to yield the title compound (isomer b; 3.9 mg). LCMS (ESI): calc. C23H24ClFN4O5=490; obs. M+H=491.2. Retention time: 1.99 min. [0441] 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 3.6 minutes, then 100% B for 1.0 minute, detection at 254 nm
The synthetic route of 16681-70-2 has been constantly updated, and we look forward to future research findings.
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