Water → 6-[5-amino-3-phenyl-6-(1H-pyrazol-1-yl)-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone

HRID 915072Notes

Reaction equation

[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.[NH2:8][C:9]1[N:10]=[C:11]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:12]([C:16]2[CH:17]=[CH:18][C:19](=[O:25])[N:20]([CH:22]([CH3:24])[CH3:23])[N:21]=2)=[N:13][C:14]=1Br.O>C(Cl)(Cl)Cl.CC(C)=O>[NH2:8][C:9]1[N:10]=[C:11]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:12]([C:16]2[CH:17]=[CH:18][C:19](=[O:25])[N:20]([CH:22]([CH3:24])[CH3:23])[N:21]=2)=[N:13][C:14]=1[N:3]1[CH:7]=[CH:6][CH:5]=[N:4]1

Participants

Conditions

Temperature: 27.5 °C

Procedure

To a suspension of NaH (60% in oil suspension) (23.3 mg) in 1,2-dimethyl-2-imidazolidinone (0.3 ml) was added 1H-pyrazole (42.3 mg) and the mixture was stirred at 25-30° C. for 30 minutes. After addition of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (150 mg), the mixture was heated at 120-125° C. for 15 hours. To the reaction mixture was added water (3 ml) to give a precipitate. The precipitate was dissolved in CHCl3, dried over MgSO4 and concentrated under reduced pressure to give a solid. The solid was suspended in acetone and collected by filtration to give 6-[5-amino-3-phenyl-6-(1H-pyrazol-1-yl)-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (66 mg).

Workup

temperaturethe mixture was heated at 120-125° C. for 15 hours
customto give a precipitate
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customto give a solid
filtrationcollected by filtration

Sources & evidence

ORD record: ord-29aacc9169a5447fb8013bfa5b20686c
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

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