Ammonia → 1-{3-[3-(3,5-difluorophenyl)-6-oxo-6H-pyridazin-1-yl-methyl]phenyl}-3-methyl-6H-pyridazin-6-one

HRID 1408388

Reaktionsgleichung

C(=O)([O-])[O-].[K+].[K+].OC1C=CC=C2C=1N=CC=C2.[F:18][C:19]1[CH:20]=[C:21]([C:26]2[CH:27]=[CH:28][C:29](=[O:40])[N:30]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35](I)[CH:34]=3)[N:31]=2)[CH:22]=[C:23]([F:25])[CH:24]=1.[CH3:41][C:42]1[CH:43]=[CH:44][C:45](=[O:48])[NH:46][N:47]=1.N>CN(C=O)C.[Cu]I.C(OCC)(=O)C>[F:18][C:19]1[CH:20]=[C:21]([C:26]2[CH:27]=[CH:28][C:29](=[O:40])[N:30]([CH2:32][C:33]3[CH:34]=[C:35]([N:46]4[C:45](=[O:48])[CH:44]=[CH:43][C:42]([CH3:41])=[N:47]4)[CH:36]=[CH:37][CH:38]=3)[N:31]=2)[CH:22]=[C:23]([F:25])[CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

3.2 14.3 mg (0.08 mmol) of copper(I) iodide, 76 mg (0.55 mmol) of potassium carbonate and 11 mg (0.08 mmol) of 8-hydroxyquinoline are added to a solution of 212 mg (0.50 mmol) of 6-(3,5-difluorophenyl)-2-(3-iodobenzyl)-2H-pyridazin-3-one and 55.1 mg (0.5 mmol) of 6-methylpyridazin-3(2H)-one in 2 ml of DMF, and the mixture is heated at 120° C. for 24 hours. The reaction mixture is allowed to cool, and 10% aqueous ammonia solution and ethyl acetate are added. The resultant precipitate is filtered off with suction, washed with water and dried. The residue is boiled in ethyl acetate, filtered off with suction and washed with ethyl acetate. The residue is dried in vacuo: 1-{3-[3-(3,5-difluorophenyl)-6-oxo-6H-pyridazin-1-ylmethyl]phenyl}-3-methyl-6H-pyridazin-6-one (“A8”) as brownish crystals; ESI 407.

Aufarbeitung

temperatureto cool
filtrationThe resultant precipitate is filtered off with suction
washwashed with water
customdried
filtrationfiltered off with suction
washwashed with ethyl acetate
customThe residue is dried in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-dc5bc57d95c44ce3aef677097a96c5c1
Quelldatensatz: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08921357B2

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