1-Hydroxybenzotriazole → N,5-dimethoxy-N-methyl-4-oxo-1-phenyl-1,4-dihydropyridazine-3-carboxamide

HRID 333737Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4](=[O:18])[C:5]([C:15]([OH:17])=O)=[N:6][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1.Cl.[CH3:20][NH:21][O:22][CH3:23].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CC(N(C)C)=O.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:23][O:22][N:21]([CH3:20])[C:15]([C:5]1[C:4](=[O:18])[C:3]([O:2][CH3:1])=[CH:8][N:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:6]=1)=[O:17]

Participants

Conditions

Temperature: 50 °C

Procedure

Under an argon atmosphere, 5-methoxy-4-oxo-1-phenyl-1,4-dihydropyridazine-3-carboxylic acid (40 g) was dissolved in dimethylacetamide (600 mL) by heating to 50° C., and ice-cooled. With stirring, N,O-dimethylhydroxylamine hydrochloride (23.7 g), 1-hydroxybenzotriazole (21.9 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (46.6 g) were added, and triethylamine (81.4 mL) was added, and the mixture was allowed to warm to room temperature and stirred for 96 hr. To the reaction mixture was added ethyl acetate, and an insoluble material was filtered off. The filtrate was concentrated under reduced pressure to dryness, and the residue was purified by NH silica gel column chromatography (ethyl acetate/methanol) to give the title compound (39.2 g) as white crystals.

Workup

temperatureice-cooled
temperatureto warm to room temperature
stirringstirred for 96 hr
filtrationan insoluble material was filtered off
concentrationThe filtrate was concentrated under reduced pressure to dryness
customthe residue was purified by NH silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record: ord-79b9d579dd954b99b42b1e0dfe64983f
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883788B2

Reaction notes

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