Methyl iodide → HCID 11316420, compound

HRID 2354186Notes

Reaction equation

HRID 2354186 reaction equation
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:24]N5CCCCC5)[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:3][CH2:2]1.IC.C(=O)([O-])[O-].[K+].[K+].C(O[CH2:44][CH3:45])(=O)C>CN(C=O)C>[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH:45]5[CH2:44][CH2:14][N:13]([CH3:22])[CH2:8][CH2:7]5)[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 68453413HCID 68453413, compound

Product 1

HCID 11316420HCID 11316420, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Cyclopropyl-4-methyl-3-[4-oxo-6-(piperidin-yloxy)quinazolin-3(4H)-yl]benzamide (0.3 g), iodomethane (0.044 ml) and potassium carbonate (0.397 g) were stirred in DMF (2 ml) for 18 hours at room temperature. The reaction mixture was diluted with ethyl acetate and the organic phase was washed with water (5×), brine (2×), dried (magnesium sulfate) and concentrated. The residue was dissolved in methylene chloride (2 ml) and stirred with PS-isocyanate resin (1.25 mmol/g) (0.28 g) and MP-carbonate (2.89 mmol/g) (0.488 g) for 19 hours and then filtered and concentrated to yield the title compound (0.129 g) as a cream solid; NMR Spectrum: (DMSOd6) 0.55 (m, 2H), 0.69 (m, 2H), 1.70 (m, 2H), 1.97 (m, 2H), 2.13 (s, 3H), 2.19 (s, 3H), 2.22 (m, 2H), 2.60 (m, 2H), 2.85 (m, 1H), 4.55 (m, 1H), 7.51 (d, 1H), 7.52 (d, 1H), 7.59 (s, 1H), 7.72 (d, 1H), 7.82 (s, 1H), 7.90 (d, 1H), 8.17 (s, 1H), 8.42 (d, 1H); Mass Spectrum: M+H+ 433.

Workup

  1. washthe organic phase was washed with water (5×), brine (2×)
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in methylene chloride (2 ml)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d0f64d4a342f44769e37be5595f2791b
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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