Water → HCID 89586350, compound

HRID 1747766Notes

Reaction equation

HRID 1747766 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][CH:3]=1.[NH:29]1[CH:33]=[CH:32][CH:31]=[N:30]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.[Cu]=O>[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][C:2]([N:29]5[CH:33]=[CH:32][CH:31]=[N:30]5)=[CH:3][CH:4]=4)[N:9]=3)=[CH:19][CH:20]=[N:21]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1048PyrazoleHCID 10796Cesium carbonateHCID 68014923HCID 68014923, compound

Product 1

HCID 89586350HCID 89586350, compoundYield 36.6%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 1-(4-iodophenyl)-3-(1-phenyl-1H-pyrazol-5-yl)furo[3,2-c]pyridazin-4(1H)-one (200 mg), pyrazole (57 mg), copper oxide (6 mg), 2-hydroxybenzaldehydeoxime (23 mg) and cesium carbonate (271 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 washed with saturated brine, 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 (64 mg).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe extract was washed with saturated brine
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-6a4040212b744089b919093be6c13d66
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

Loading…