Water → 7-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-N4-(2-pyridinylmethyl)-3,4-quinolinediamine

HRID 81989Notes

Reaction equation

HRID 81989 reaction equation
O.[CH3:2][C:3]1[C:7]([C:8]2[CH:17]=[C:16]3[C:11]([C:12]([NH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)=[C:13]([N+:18]([O-])=O)[CH:14]=[N:15]3)=[CH:10][C:9]=2[O:29][CH3:30])=[C:6]([CH3:31])[O:5][N:4]=1.[H][H]>[Pd].C(OCC)(=O)C.C(O)C>[CH3:2][C:3]1[C:7]([C:8]2[CH:17]=[C:16]3[C:11]([C:12]([NH:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)=[C:13]([NH2:18])[CH:14]=[N:15]3)=[CH:10][C:9]=2[O:29][CH3:30])=[C:6]([CH3:31])[O:5][N:4]=1

Participants

7

Reactant 3

HCID 962WaterHCID 672076287-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-nitro-N-(2-pyridinylmethyl)-4-quinolinamineHCID 178418361HCID 178418361, compound

Product 1

HCID 672071317-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-N4-(2-pyridinylmethyl)-3,4-quinolinediamineYield 89%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

10% palladium on carbon, 50% water paste, (300 mg, 20% wt) was added to a solution of 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-nitro-N-(2-pyridinylmethyl)-4-quinolinamine (1.5 g, 3.70 mmol) in ethyl acetate (90 ml) and ethanol (10 ml). The reaction mixture was stirred in an atmosphere of hydrogen for 3 h. The reaction mixture was filtered through Celite™. The solvent was evaporated from the filtrate. The residue was chromatographed [5% methanol/DCM] to give the title compound as a brown oil (1.23 g, 3.28 mmol, 89% yield). LCMS (formate) Rt 0.63 min, MH+ 376

Workup

  1. filtrationThe reaction mixture was filtered through Celite™
  2. customThe solvent was evaporated from the filtrate
  3. customThe residue was chromatographed [5% methanol/DCM]

Sources & evidence

ORD record
ord-d233a08031f041f3b3c4b80c46e3a8ff
Source dataset
uspto-grants-2014_09
Patent number
US08846709B2

Reaction notes

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