Water → HCID 68014809, compound

HRID 1747768Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]3[CH:14]=[CH:15][O:16][C:12]=3[C:11](=[O:17])[C:10]([C:18]3[N:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[N:21]=[CH:20][CH:19]=3)=[N:9]2)=[CH:4][C:3]=1[O:29][C:30]([F:33])([F:32])[F:31].N1C=CC=N1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[C:23]1([N:22]2[C:18]([C:10]3[C:11](=[O:17])[C:12]4[O:16][CH:15]=[CH:14][C:13]=4[N:8]([C:5]4[CH:6]=[CH:7][CH:2]=[C:3]([O:29][C:30]([F:33])([F:32])[F:31])[CH:4]=4)[N:9]=3)=[CH:19][CH:20]=[N:21]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 1-[4-iodo-3-(trifluoromethoxy)phenyl]-3-(1-phenyl-1H-pyrazol-5-yl)furo[3,2-c]pyridazin-4(1H)-one (300 mg), pyrazole (72 mg), copper oxide(I) (7.6 mg), 2-hydroxybenzaldehydeoxime (29 mg) and cesium carbonate (346 mg) in DMF (5 mL) was stirred at 50° C. for 12 hr, and water was added. The reaction mixture was extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (25 mg).

Workup

extractionThe reaction mixture was extracted with ethyl acetate
dry with materialthe extract was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record: ord-91395d525f4f4937acf644e80655620e
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150588B2

Reaction notes

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