6-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-[(4-methoxybenzyl)amino]-5-phenyl-2-pyrazinecarboxylic acid → 2-isopropyl-6-{6-[(4-methoxybenzyl)amino]-3-phenyl-2-pyrazinyl}-3(2H)-pyridazinone

HRID 915039Notes

Reaction equation

C(N1C(=O)C=CC(C2N=C(C(O)=O)C(NCC3C=CC(OC)=CC=3)=NC=2C2C=CC=CC=2)=N1)(C)C.[CH:36]([N:39]1[C:44](=[O:45])[CH:43]=[CH:42][C:41]([C:46]2[N:47]=[C:48]([NH:61][CH2:62][C:63]3[CH:68]=[CH:67][C:66]([O:69][CH3:70])=[CH:65][CH:64]=3)[C:49](C(O)=O)=[N:50][C:51]=2[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[N:40]1)([CH3:38])[CH3:37]>ClC1C=CC=CC=1Cl>[CH:36]([N:39]1[C:44](=[O:45])[CH:43]=[CH:42][C:41]([C:46]2[C:51]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)=[N:50][CH:49]=[C:48]([NH:61][CH2:62][C:63]3[CH:64]=[CH:65][C:66]([O:69][CH3:70])=[CH:67][CH:68]=3)[N:47]=2)=[N:40]1)([CH3:38])[CH3:37]

Participants

Conditions

Temperature: 177.5 °C

Procedure

A suspension of a mixture of 6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-[(4-methoxybenzyl)amino]-5-phenyl-2-pyrazinecarboxylic acid and 5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-[(4-methoxybenzyl)amino]-6-phenyl-2-pyrazinecarboxylic acid (9.34 g) in o-dichlorobenzene (37 ml) was heated at 175-180° C. for 5 hours. After cooling, the reaction mixture was purified by column chromatography on silica gel. By eluting with a mixture of n-hexane and EtOAc (50:50 v/v) was obtained 2-isopropyl-6-{6-[(4-methoxybenzyl)amino]-3-phenyl-2-pyrazinyl}-3(2H)-pyridazinone as a solid (4.41 g) and by eluting with a mixture of n-hexane and EtOAc (40:60 v/v) was obtained 2-isopropyl-6-{5-[(4-methoxybenzyl)amino]-3-phenyl-2-pyrazinyl}-3(2H)-pyridazinone as a solid (2.38 g).

Workup

temperatureAfter cooling
customthe reaction mixture was purified by column chromatography on silica gel
washBy eluting with a mixture of n-hexane

Sources & evidence

ORD record: ord-8f8d98ca5c204d2a85e9f4a6f7d80358
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

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