HCID 89586363, compound → HCID 89586088, compound

HRID 1747763Notes

Reaction equation

HRID 1747763 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:5]=[CH:4][C:3]=1[N:13]1[C:18]2[CH:19]=[CH:20][O:21][C:17]=2[C:16](=[O:22])[C:15]([C:23]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:26]=[CH:25][CH:24]=2)=[N:14]1>[Pd].C(O)C.C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:5]=[CH:4][C:3]=1[N:13]1[C:18]2[CH2:19][CH2:20][O:21][C:17]=2[C:16](=[O:22])[C:15]([C:23]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:26]=[CH:25][CH:24]=2)=[N:14]1

Participants

4

Reactant 1

HCID 89586363HCID 89586363, compound

Product 1

HCID 89586088HCID 89586088, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 1-[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]-3-(1-phenyl-1H-pyrazol-5-yl)furo[3,2-c]pyridazin-4(1H)-one (100 mg) and 10% palladium on carbon (100 mg) in ethanol/THF (3/1, 40 mL) was stirred at 50° C. for 12 hr under a hydrogen atmosphere. Palladium on carbon was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) and crystallized from hexane/ethyl acetate to give the title compound (74 mg).

Workup

  1. customPalladium on carbon was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)
  4. customcrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-9397920b1a0542f494b744e9cea2f1e2
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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