Hydrochloric Acid → 6-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-methoxy-5-phenyl-2-pyrazinecarbonitrile

HRID 915029Notes

Reaction equation

[CH3:1][O-:2].[Na+].[CH:4]([N:7]1[C:12](=[O:13])[CH:11]=[CH:10][C:9]([C:14]2[N:15]=[C:16]([C:28]#[N:29])[C:17](C#N)=[N:18][C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:8]1)([CH3:6])[CH3:5].Cl.O>CO.C(Cl)(Cl)Cl>[CH:4]([N:7]1[C:12](=[O:13])[CH:11]=[CH:10][C:9]([C:14]2[N:15]=[C:16]([C:28]#[N:29])[C:17]([O:2][CH3:1])=[N:18][C:19]=2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:8]1)([CH3:5])[CH3:6]

Participants

Conditions

Temperature: 27.5 °C

Procedure

To a solution of sodium methoxide (81.5 mg) in MeOH (3 ml), 5-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-6-phenyl-2,3-pyrazinedicarbonitrile (172 mg) was added and the mixture was stirred at 25-30° C. for 10 hours. After addition of conc. HCl (1.5 ml), the reaction mixture was stirred at 25-30° C. for 20 hours. Water and CHCl3 were added to the mixture. An organic layer was collected, dried over MgSO4, concentrated under reduced pressure and subjected to column chromatography on silica gel. With elution of a mixture of n-hexane and EtOAc (70:30 v/v) was obtained 6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-methoxy-5-phenyl-2-pyrazinecarbonitrile as a solid (43 mg) and with elution of a mixture of n-hexane and EtOAc (50:50 v/v) was obtained methyl 6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-methoxy-5-phenyl-2-pyrazinecarboxylate as a solid (67 mg).

Workup

stirringthe reaction mixture was stirred at 25-30° C. for 20 hours
customAn organic layer was collected
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
washWith elution of a mixture of n-hexane

Sources & evidence

ORD record: ord-9a52cf92d51f4cf7902519adb3ab37e8
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

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