Benzene → 7-(3,5-dimethyl-4-isoxazolyl)-1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-8-(methyloxy)-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one

HRID 1043019Notes

Reaction equation

HRID 1043019 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:20][CH2:21][C:22]4[S:26][C:25]([CH3:27])=[N:24][C:23]=4[CH3:28])=[C:12](C(N)=O)[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:29][CH3:30])=[C:5]([CH3:31])[O:4][N:3]=1.C1C=CC=CC=1.[OH2:38].[C:39](#[N:41])C>>[CH3:1][C:2]1[C:6]([C:7]2[C:8]([O:29][CH3:30])=[CH:9][C:10]3[C:11]4[N:20]([CH2:21][C:22]5[S:26][C:25]([CH3:27])=[N:24][C:23]=5[CH3:28])[C:39](=[O:38])[NH:41][C:12]=4[CH:13]=[N:14][C:15]=3[CH:16]=2)=[C:5]([CH3:31])[O:4][N:3]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 6342AcetonitrileHCID 574655937-(3,5-Dimethyl-4-isoxazolyl)-4-{[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]amino}-6-(methyloxy)-3-quinolinecarboxamide

Product 1

HCID 529345057-(3,5-dimethyl-4-isoxazolyl)-1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-8-(methyloxy)-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one

Procedure

To a solution of 7-(3,5-dimethyl-4-isoxazolyl)-4-{[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]amino}-6-(methyloxy)-3-quinolinecarboxamide (for a preparation see intermediate 65, 0.3 g) in acetonitrile (50 ml) was added bis(trifluoroacetoxy)iodo]benzene (0.443 g) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then poured into water and extracted with DCM. The organic phase was dried over Na2SO4 and concentrated to dryness to give an orange oil. The residue was purified by flash chromatography on silica gel eluting with DCM/methanol (98: 2 then 97:3) give a sticky pale yellow solid, which was triturated in hot diisopropylether to give 7-(3,5-dimethyl-4-isoxazolyl)-1-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-8-(methyloxy)-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one (0.21 g) as a cream coloured solid.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated to dryness
  4. customto give an orange oil
  5. customThe residue was purified by flash chromatography on silica gel eluting with DCM/methanol (98: 2
  6. custom97:3) give a sticky pale yellow solid, which
  7. customwas triturated in hot diisopropylether

Sources & evidence

ORD record
ord-9c3e7c1e47a742ac843f4a3fdba6e8ae
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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