Dimethylformamide → HCID 68994032, compound

HRID 657116Notes

Reaction equation

HRID 657116 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[N:10]([CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22][CH2:21]2)[C:9](=[O:34])[CH:8]=1)(=O)=O.[CH3:37][N:38](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:37]([C:7]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[N:10]([CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][CH:23]([NH:26][C:27](=[O:28])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])[CH2:24][CH2:25]2)[C:9](=[O:34])[CH:8]=1)#[N:38]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 86635358HCID 86635358, compound

Product 1

HCID 68994032HCID 68994032, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
90 °C

Procedure

To a solution of 1-{2-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]ethyl}-7-fluoro-2-oxo-1,2-dihydro-4-quinolinyl trifluoromethanesulfonate (0.17 g, 0.32 mmol) in DMF (10 ml) was added zinc cyanide (0.036 g, 0.3 mmol), tris(dibenzylideneacetone)dipalladium (0.022 g, 0.024 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (0.056 g, 0.1 mmol) and degassed with argon. The mixture was heated at 90° C. for 18 h. The solution was allowed to cool then separated between ethyl acetate and brine. The organics were dried and concentrated then the residues combined with the crude from a similar experiment conducted on half the scale. Chromatography of the combined material over silica (10 g SPE gradient elution with ethyl acetate/methanol 0-3%) provided a brown oil which solidified as the title compound (0.113 g, 46%).

Workup

  1. customdegassed with argon
  2. temperatureto cool
  3. customthen separated between ethyl acetate and brine
  4. customThe organics were dried
  5. concentrationconcentrated
  6. customChromatography of the combined material over silica (10 g SPE gradient elution with ethyl acetate/methanol 0-3%) provided a brown oil which

Sources & evidence

ORD record
ord-00788b02b76344efb208e32d98f47417
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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