Pyridine → HCID 68703823, compound

HRID 1624893Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[N:7][NH:6][C:5](=[O:9])[N:4]=1.[C:10]([NH:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)(=[O:12])[CH3:11].N1C=CC=CC=1>CN(C=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[N:7][N:6]([C:18]2[CH:19]=[C:14]([NH:13][C:10](=[O:12])[CH3:11])[CH:15]=[CH:16][CH:17]=2)[C:5](=[O:9])[N:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

According to Scheme 6 Step 1: To a stirred solution of 5-methoxy-1,2,4-triazin-3(2H)-one (1 g, 7.9 mmol) in DMF (5 mL) were successively added the 3-acetamidophenylboronic acid (1.4 g, 7.9 mmol), copper(II) acetate (1.4 g, 7.9 mmol) and pyridine (1.2 g, 7.9 mmol). The mixture was stirred overnight at 60° C. The reaction mixture was quenched with a saturated sodium bicarbonate solution and extracted with ethyl acetate (×3). The combined organic layers were washed successively with water, brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography, 70 g column, CH2Cl2/MeOH 98/2 to afford (0.493 g, 24%) of N-(3-(5-methoxy-3-oxo-1,2,4-triazin-2(3H)-yl)phenyl)acetamide

Workup

customThe reaction mixture was quenched with a saturated sodium bicarbonate solution
extractionextracted with ethyl acetate (×3)
washThe combined organic layers were washed successively with water, brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash chromatography, 70 g column, CH2Cl2/MeOH 98/2

Sources & evidence

ORD record: ord-b26a3a359049432d963ca4474aaf1930
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779129B2

Reaction notes

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