Benzene → HCID 52934731, compound

HRID 1043018Notes

Reaction equation

HRID 1043018 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:14]3[C:15]([CH3:20])=[N:16][O:17][C:18]=3[CH3:19])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1C(N)=O.[N:24]1[CH:29]=[CH:28][N:27]=[CH:26][C:25]=1[CH2:30][NH2:31].[C:32](=[O:35])([O-])O.[Na+].C1C=CC=CC=1.C(#[N:45])C>>[CH3:20][C:15]1[C:14]([C:8]2[C:9]([O:12][CH3:13])=[CH:10][C:11]3[C:2]4[N:24]([CH2:29][C:28]5[N:27]=[CH:26][CH:25]=[CH:30][N:31]=5)[C:32](=[O:35])[NH:45][C:3]=4[CH:4]=[N:5][C:6]=3[CH:7]=2)=[C:18]([CH3:19])[O:17][N:16]=1

Participants

6

Reactant 5

HCID 241BenzeneHCID 6342Acetonitrile2×HCID 266781(Pyrazin-2-yl)methanamineHCID 516892Sodium BicarbonateHCID 574655814-Chloro-7-(3,5-dimethylisoxazol-4-yl)-6-methoxyquinoline-3-carboxamide2×

Product 1

HCID 52934731HCID 52934731, compound

Procedure

In a 100 ml flask a mixture of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-quinolinecarboxamide (for a preparation see Intermediate 56, 331 mg,) and (2-pyrazinylmethyl)amine (2.5 eq) in acetonitrile was heated at 100° C. for 2 h. The reaction mixture was hydrolyzed with a solution of sodium hydrogen carbonate, extracted with DCM and the organic dried over Na2SO4, filtered and concentrated to dryness to give the crude intermediate. The residue was dissolved in acetonitrile (15 ml), bis(trifluoroacetoxy)iodo]benzene (0.5 g) was added and the reaction mixture was stirred for 3 h at room temperature. The reaction mixture was washed with water, extracted with DCM and the organic were dried over Na2SO4, filtered and concentrated to dryness. The resulting crude compound was purified by chromatography on silica gel eluting with DCM/methanol (95:5) and the resulting residue was recrystallised from acetonitrile and dried in vacuo to give 7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-1-(2-pyrimidinylmethyl)-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one (100 mg) as a beige powder.

Workup

  1. extractionextracted with DCM
  2. dry with materialthe organic dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customto give the crude intermediate
  6. washThe reaction mixture was washed with water
  7. extractionextracted with DCM
  8. dry with materialthe organic were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to dryness
  11. customThe resulting crude compound was purified by chromatography on silica gel eluting with DCM/methanol (95:5)
  12. customthe resulting residue was recrystallised from acetonitrile
  13. customdried in vacuo

Sources & evidence

ORD record
ord-2680523a468b4327b696917650ed690c
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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