1-Phenyl-1-propanol → 1-Mesityl-6-methyl-4-(1-phenylpropoxy)-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one

HRID 598144Notes

Reaction equation

[C:1]1([CH:7]([OH:10])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:14]1[C:15]2[CH:24]=[CH:23][N:22]([C:25]3[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[CH:27][C:26]=3[CH3:33])[C:16]=2[C:17](=[O:21])[N:18]([CH3:20])[N:19]=1>CN(C=O)C.O>[C:26]1([CH3:33])[CH:27]=[C:28]([CH3:32])[CH:29]=[C:30]([CH3:31])[C:25]=1[N:22]1[C:16]2[C:17](=[O:21])[N:18]([CH3:20])[N:19]=[C:14]([O:10][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH3:9])[C:15]=2[CH:24]=[CH:23]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-phenyl-1-propanol (0.061 ml, 0.45 mmol) in DMF (1 ml) was added sodium hydride (60% in oil, 18 mg, 0.45 mmol). The mixture was stirred for 10 min before addition of 4-chloro-1-mesityl-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one (45.3 mg, 0.15 mmol). The mixture was stirred at 60° C. for 1 hour, then diluted with water (30 ml) and extracted with ethyl acetate (50 ml). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate (5:1) to give 49.4 mg (82%) of the title compound as an oil.

Workup

extractionextracted with ethyl acetate (50 ml)
washThe extract was washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography
washeluting with hexane/ethyl acetate (5:1)

Sources & evidence

ORD record: ord-240a360d5941473180cd4b3c4b162e5f
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897607B2

Reaction notes

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