Acetone → HCID 69331883, compound

HRID 915064Notes

Reaction equation

C1(P([C:14]2[CH:19]=[CH:18]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(C(C)C)CC)(C)C.[NH2:29][C:30]1[N:31]=[C:32]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:33]([C:37]2[CH:38]=[CH:39][C:40](=[O:46])[N:41]([CH:43]([CH3:45])[CH3:44])[N:42]=2)=[N:34][C:35]=1Br.[OH2:53].[CH3:54][C:55](C)=[O:56]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:29][C:30]1[C:35]([CH:18]=[CH:19][C:14]([O:56][CH2:55][CH3:54])=[O:53])=[N:34][C:33]([C:37]2[CH:38]=[CH:39][C:40](=[O:46])[N:41]([CH:43]([CH3:45])[CH3:44])[N:42]=2)=[C:32]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[N:31]=1

Participants

Conditions

Temperature: 102.5 °C

Procedure

In the presence of palladium acetate (14.6 mg) and triphenylphosphine (34.0 mg), diisopropylethylamine (0.687 ml) was added to a mixture of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (501 mg) in DMF (2 ml) and the mixture was heated at 100-105° C. for 20 hours. After addition of water, a precipitate was collected by filtration and purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (50:50 v/v) to give a solid. The solid was suspended in acetone and collected by filtration to give ethyl 3-[3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinyl]acrylate (95 mg).

Workup

filtrationa precipitate was collected by filtration
custompurified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (50:50 v/v)
customto give a solid
filtrationcollected by filtration

Sources & evidence

ORD record: ord-84307cfc9c4543feb7313c200f1489b1
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

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