Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 138624-97-2, name is 1-Benzyl-1H-1,2,4-triazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H9N3O2
A mixture of 1-benzyl-1H-1,2,4-triazole-3-carboxylic acid (32 mg, 0.16 mmol), 1-(3- dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (28 mg, 0.14 mmol), 3-amino-i – methyl-4,5-dihydro-3h-pyrido [1,2-a] [1,3] diazepine-2,7-dione (25 mg, 0.12 mmol) and 1- hydroxybenzotriazole (20 mg, 0.14 mmol) in N,N-dimethylformamide (3 mL) was stuffed at 25 C for 12 h. The mixture was concentrated to dryness under reduce pressure. The resultingresidue was purified by reverse phase chromatography (acetonitrile 10-40% / 0.05% ammonia hydroxide in water) to afford 1 -benzyl-N-( 1 -methyl-2,7-dioxo- 1,2,3,4,5,7- hexahydropyrido [1,2-a] [1,3] diazepin-3-yl)- 1 H-i ,2,4-triazole-3-carboxamide (30 mg, 63%) as a white solid. The racemic material was further purified by SFC to give arbitrarily assigned:1 -benzyl-N-[(3S)- 1 -methyl-2,7-dioxo-4,5-dihydro-3H-pyrido[ 1,2-a] [1 ,3]diazepin-3-yl]-1,2,4-triazole-3-carboxamide (Peak 1, retention time = 5.180 mm) (12 mg, 40%) as white solids. ?H NMR (400 MHz, CD3OD) 5 8.57 (s, 1H), 7.64 – 7.56 (m, 1H), 7.47 – 7.25 (m, 5H), 6.53 (d, J = 9.2 Hz, 1H), 6.46 (d, J = 7.2 Hz, 1H), 5.47 (s, 2H), 5.07 – 5.03 (m, 1H),4.61 – 4.55 (m, 1H), 3.71 – 3.63 (m, 1H), 3.39 (s, 3H), 2.68 – 2.60 (m, 1H), 2.19 – 2.12 (m, 1H). LC-MS RT = 1.177 mm, mlz = 393.2 [M+H]. LCMS (10 to 80% acetonitrile in water +0.03% ammonium bicarbonate over 3.0 mins) retention time 1.177 mm, ESI+ found [M+H] =393.2.1 -benzyl-N- [(3R)- 1 -methyl-2,7-dioxo-4,5-dihydro-3H-pyrido [1,2-a] [1,3] diazepin-3-yl]-1,2,4-triazole-3-carboxamide. (Peak 2, retention time = 6.616 mm) (8 mg, 26%) as white solids. ?H NMR (400 MHz, CD3OD) (5 8.56 (s, 1H), 7.63 – 7.57 (m, 1H), 7.43 – 7.25 (m, 5H), 6.52 (d, J = 9.2 Hz, 1H), 6.45 (d, J = 7.2 Hz, 1H), 5.47 (s, 2H), 5.06 – 5.01 (m, 1H),4.59 – 4.56 (m, 1H), 3.69 – 3.62 (m, 1H), 3.39 (s, 3H), 2.68 – 2.60 (m, 1H), 2.19 – 2.12 (m, 1H). LC-MS RT = 1.179 mi mlz = 393.1 [M+Hf?. LCMS (10 to 80% acetonitrile in water +0.03% ammonium bicarbonate over 3.0 mins) retention time 1.179 mi ESI+ found [M+H] =393.1.SFC condition: column: chiralcel OD-3 100 x 4.6mm I.D., 3um mobile phase:A:C02 B: ethanol (0.05% DEA) gradient: hold 5% for 1.0 mm, then from 5% to 40% of B in 4.5 mm and hold 40% for 2.5 mm, then 5% of B for 1.0 mm. Flow rate: 2.8 mL/min. Columntemperature: 40 C.
The synthetic route of 138624-97-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; (105 pag.)WO2018/73193; (2018); A1;,
1,2,3-Triazole – Wikipedia,
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