Benzene → HCID 52934731, compound

HRID 1043017Notes

Reaction equation

HRID 1043017 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][CH:27]=[N: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:31]([CH2:30][C:25]5[N:26]=[CH:27][CH:28]=[CH:29][N:24]=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 516892Sodium BicarbonateHCID 46580472-PyrimidinemethanamineHCID 574655814-Chloro-7-(3,5-dimethylisoxazol-4-yl)-6-methoxyquinoline-3-carboxamide2×

Product 1

HCID 52934731HCID 52934731, compound

Conditions

Temperature
100 °C

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-pyrimidinylmethyl)amine (273 mg) 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 350 mg of 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 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 (70 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 350 mg of crude intermediate
  6. washThe reaction mixture was washed with water
  7. extractionextracted with DCM
  8. dry with materialthe organic 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-50a62b575d7c41c689d3f9ed88a039ad
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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