Dimethylformamide dimethyl acetal → 3-[3-(dimethylamino)prop-2-enoyl]-1-[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]-5-methoxypyridazin-4(1H)-one

HRID 1528046Notes

Reaction equation

[C:1]([C:4]1[C:9](=[O:10])[C:8]([O:11][CH3:12])=[CH:7][N:6]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:23]=[CH:22][CH:21]=[N:20]3)=[CH:15][C:14]=2[F:24])[N:5]=1)(=[O:3])[CH3:2].CO[CH:27](OC)[N:28]([CH3:30])[CH3:29]>C(#N)C>[CH3:27][N:28]([CH3:30])[CH:29]=[CH:2][C:1]([C:4]1[C:9](=[O:10])[C:8]([O:11][CH3:12])=[CH:7][N:6]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:23]=[CH:22][CH:21]=[N:20]3)=[CH:15][C:14]=2[F:24])[N:5]=1)=[O:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-acetyl-1-[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]-5-methoxypyridazin-4(1H)-one (600 mg), N,N-dimethylformamide dimethyl acetal (3 mL) and acetonitrile (3 mL) was stirred at 80° C. for 12 hr, allowed to be cooled to room temperature, and stirred for 12 hr. The precipitate was collected by filtration, and washed with diisopropyl ether to give the title compound (600 mg).

Workup

temperatureto be cooled to room temperature
stirringstirred for 12 hr
filtrationThe precipitate was collected by filtration
washwashed with diisopropyl ether

Sources & evidence

ORD record: ord-ee53e2e0ba5246b384d51b03c0fd87e3
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090586B2

Reaction notes

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