HCID 91354783, compound → HCID 67232750, compound

HRID 1406470Notes

Reaction equation

HRID 1406470 reaction equation
[NH2:1][C:2]1[C:17]([N+:18]([O-])=O)=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][N:10]=2)=[O:7])=[C:4]([F:21])[CH:3]=1.[H][H]>C1COCC1.[Ni]>[NH2:1][C:2]1[C:17]([NH2:18])=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][N:10]=2)=[O:7])=[C:4]([F:21])[CH:3]=1

Participants

5

Reactant 2

HCID 91354783HCID 91354783, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67232750HCID 67232750, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product obtained at 142f (320 mg, 1.0 mmol) in 20 mL THF was combined with Raney nickel (70 mg) and hydrogenated in a Parr apparatus at ambient temperature for 1.5 days at 3 bar hydrogen pressure. Then the mixture is filtered and concentrated i.vac. The residue is purified by chromatography on RP-HPLC (stable bond C18, 5 μm). The mixture was concentrated i.vac., taken up in water and treated with K2CO3. The aq. phase is diluted with ethyl acetate. The organic phase is dried, filtered and concentrated i.vac.

Workup

  1. filtrationThen the mixture is filtered
  2. concentrationconcentrated i.vac
  3. customThe residue is purified by chromatography on RP-HPLC (stable bond C18, 5 μm)
  4. concentrationThe mixture was concentrated i.vac
  5. additiontreated with K2CO3
  6. additionThe aq. phase is diluted with ethyl acetate
  7. customThe organic phase is dried
  8. filtrationfiltered
  9. concentrationconcentrated i.vac

Sources & evidence

ORD record
ord-c3a191ca78a8415aacbf24460121b22b
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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