Water → N-(2-{[3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinyl]amino}ethyl)acetamide

HRID 915069Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[N:14]=2)=[N:6][C:7]=1Br.[NH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:31])[CH3:30].O>C(Cl)(Cl)Cl.CC(C)=O>[NH2:1][C:2]1[C:7]([NH:25][CH2:26][CH2:27][NH:28][C:29](=[O:31])[CH3:30])=[N:6][C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[N:14]=2)=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:3]=1

Participants

Conditions

Temperature: 122.5 °C

Procedure

A mixture of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (150 mg) and N-(2-aminoethyl)acetamide (0.112 ml) in 1,2-dimethyl-2-imidazolidinone (0.3 ml) was heated at 120-125° C. for 50 hours. After addition of water (3 ml), an aqueous layer was removed by decantation to give a residue. The residue was dissolved in CHCl3, dried over MgSO4, concentrated under reduced pressure and purified by column chromatography on silica gel eluting with a mixture of MeOH and EtOAc (3:97 v/v) to give a solid. The solid was suspended in acetone to give N-(2-{[3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinyl]amino}ethyl)acetamide (28 mg).

Workup

customan aqueous layer was removed by decantation
customto give a residue
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
custompurified by column chromatography on silica gel eluting with a mixture of MeOH and EtOAc (3:97 v/v)
customto give a solid

Sources & evidence

ORD record: ord-a0c9a8dc9b8740599cd55d0e4ed6d6f9
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

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