Tetrahydrofuran → Methyl 3-(5-methylpyridin-2-yl)-5-(4-methyl-4H-1,2,4-triazol-3-yl)benzoate

HRID 888383Notes

Reaction equation

[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][N:16]=2)[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])=S.C([NH:24][NH2:25])=O.[CH2:26]1COCC1>C([O-])(=O)C.[Hg+]>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[CH:12]=[C:7]([CH:6]=[C:5]([C:3]3[N:2]([CH3:26])[CH:1]=[N:25][N:24]=3)[CH:14]=2)[C:8]([O:10][CH3:11])=[O:9])=[N:16][CH:17]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of methyl 3-[(methylamino)carbonothioyl]-5-(5-methylpyridin-2-yl)benzoate (0.90 g, 3.00 mmol) in THF (30 mL) was added formic hydrazide (0.54 g, 8.99 mmol) and mercury acetate (1.72 g, 5.39 mmol) and the mixture heated to 40° C. After 16 h, the reaction was cooled to ambient temperature, filtered and concentrated. The organic residue was dissolved in 100 ml of dichloromethane and washed with 50 mL of saturated aqueous sodium bicarbonate (2×). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol) to give the title compound (0.37 g). MS 309.1 (M+1).

Workup

temperaturethe reaction was cooled to ambient temperature
filtrationfiltered
concentrationconcentrated
dissolutionThe organic residue was dissolved in 100 ml of dichloromethane
washwashed with 50 mL of saturated aqueous sodium bicarbonate (2×)
dry with materialThe combined organic extracts were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography (100% dichloromethane→90% dichloromethane/methanol)

Sources & evidence

ORD record: ord-9baf22b7b0d84bc5876adbbcc9991bde
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247401B2

Reaction notes

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