199460-26-9 → HCID 54910855, compound

HRID 1639543Notes

Reaction equation

HRID 1639543 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:13]=2[CH3:21])=[O:10])[CH:5]=[CH:6][CH:7]=1.[H][H]>CN(C)C=O.[Pd]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[O:10])=[C:13]([CH3:21])[CH:14]=1

Participants

5

Reactant 2

HCID 307729199460-26-9HCID 178418361HCID 178418361, compound

Product 1

HCID 54910855HCID 54910855, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of EXAMPLE 100A (1.28 g, 4.43 mmol) in 12 mL of N,N-dimethylformamide was degassed and hydrogenated under an atmosphere of hydrogen (balloon) in the presence of catalytic amount of 10% Pd on carbon for 24 hours. The mixture was filtered and the filtrate was extracted with ethyl acetate. The organic extract was washed with brine, dried with MgSO4 and concentrated to provide EXAMPLE 100B. MS (ESI(+)) m/e 260 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. extractionthe filtrate was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customto provide EXAMPLE 100B

Sources & evidence

ORD record
ord-a1715004a5b34245a60cbce0ed4c6808
Source dataset
uspto-grants-2012_02
Patent number
US08110572B2

Reaction notes

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