Synthetic Route of 138624-97-2, New Advances in Chemical Research in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 138624-97-2, name is 1-Benzyl-1H-1,2,4-triazole-3-carboxylic acid, molecular formula is C10H9N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.
A mixture of (3S)-3-amino- 1 ,8-dimethyl-4,5-dihydro-3H-pyrido[3,4-b] azepine-2,7- dione (15 mg, 0.07 mmol), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimidehydrochloride (16 mg, 0.08 mmol), i-hydroxybenzotriazole (ii mg, 0.08 mmol) and i-benzyl-i,2,4- triazole-3-carboxylic acid (17 mg, 0.08 mmol) in N,N-dimethylformamide (3 mL) was stirredat 25 C for 2 h. The mixture was concentrated under reduced pressure and the residue was purified by RP-HPLC (acetonitrile 20-50%/0.05% ammonium hydroxide in water) to afford arbitrarily assigned (S)- 1 -benzyl-N-( 1 ,8-dimethyl-2,7-dioxo-2,3,4,5,7,8-hexahydro- 1H- pyrido[3,4-b]azepin-3-yl)-1H-i,2,4-triazole-3-carboxamide (22.2 mg, 78%) as a white solid. ?H NMR (400 MHz, CD3OD) 8.56 (s, 1H), 7.87 (s, 1H), 7.37 – 7.33 (m, 5H), 6.49 (s, 1H),5.46 (s, 2H), 4.71 – 4.65 (m, 1H), 3.59 (s, 3H), 3.32 (s, 3H), 2.74 – 2.68 (m, 2H), 2.45 – 2.38 (m, 1H), 2.13 – 2.08 (m, 1H). LCMS RT = 0.697 mm, m/z = 407.1 [M + H]. LCMS (5 to 95% acetonitrile in water + 0.1% formic acid over 1.5 mins) retention time 0.697 mi ESI+
The result showed that such a combination of chemo- and biocatalysis improved the catalytic yield more than two times compared with that of sole metal catalysis.I hope my blog about 1-Benzyl-1H-1,2,4-triazole-3-carboxylic acid is helpful to your research.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; (105 pag.)WO2018/73193; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics