1H-1,2,4-Triazole-3-carboxylic acid, 5-amino-, ethyl ester → HCID 136133158, compound

HRID 2200927Notes

Reaction equation

[NH2:1][C:2]1[N:6]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[NH:4][N:3]=1.[C:12]([C:14]1[CH:29]=[CH:28][C:17]([CH:18]=[C:19]([C:25](=O)[CH3:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=1)#[N:13].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:12]([C:14]1[CH:29]=[CH:28][C:17]([CH:18]2[N:3]3[N:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=[C:2]3[NH:1][C:25]([CH3:26])=[C:19]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=1)#[N:13]

Participants

Conditions

Temperature: 55 °C

Procedure

Under an atmosphere of argon, ethyl 3-amino-1H-1,2,4-triazole-5-carboxylate (700 mg, 4.4 mmol) and ethyl 2-(4-cyanobenzylidene)-3-oxobutanoate (1.18 g, 4.9 mmol, 1.1 eq.) were dissolved in DMF (5 ml), and solid sodium bicarbonate (1.86 g, 22.1 mmol, 5 eq.) was added. The mixture was stirred at 55° C. for 6 h. The mixture was then filtered, and the DMF from the filtrate was distilled off under reduced pressure. The residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (1.3 g, 80% of theory).

Workup

filtrationThe mixture was then filtered
distillationthe DMF from the filtrate was distilled off under reduced pressure
customThe residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
customAfter lyophilization, the product was obtained as a solid (1.3 g, 80% of theory)

Sources & evidence

ORD record: ord-c8a2d35dd6574da793c629eb26410ccf
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359362B2

Reaction notes

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