Water → HCID 69333199, compound

HRID 915071Notes

Reaction equation

[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[CH: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>O1CCOCC1.C(Cl)(Cl)Cl>[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]=[CH:4]1

Participants

Conditions

Temperature: 27.5 °C

Procedure

To a suspension of NaH (60% in oil suspension) (77.7 mg) in dioxane (0.6 ml) was added 1H-pyrrole (0.161 ml) 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 100-105° C. for 2 hours. A mixture of water and chloroform was added to the reaction mixture. An organic layer was collected, dried over MgSO4, concentrated under reduced pressure and purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (75:25 v/v) to give a solid. The solid was crystallized from a mixture of IPE and n-hexane to give 6-[5-amino-3-phenyl-6-(1H-pyrrol-1-yl)-2-pyrazinyl]-2-isopropyl-3(2H)-pyridazinone (38 mg).

Workup

temperaturethe mixture was heated at 100-105° C. for 2 hours
additionwas added to the reaction mixture
customAn organic layer was collected
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
custompurified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (75:25 v/v)
customto give a solid
customThe solid was crystallized from a mixture of IPE and n-hexane

Sources & evidence

ORD record: ord-bd170e3d1a4646bdb9b1fc43d07f5d38
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265120B2

Reaction notes

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