Methyl iodide → HCID 11774423, compound

HRID 2354194Notes

Reaction equation

HRID 2354194 reaction equation
[CH:1]1([NH:4][C:5](=[O:30])[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:25]5[CH2:29][NH:28][CH2:27][CH2:26]5)[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:3][CH2:2]1.IC.[C:33](=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.C(OCC)(=O)C>[CH:1]1([NH:4][C:5](=[O:30])[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:25]5[CH2:26][CH2:27][N:28]([CH3:33])[CH2:29]5)[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11441074HCID 11441074, compound

Product 1

HCID 11774423HCID 11774423, compoundYield 39.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

N-Cyclopropyl-4-methyl-3-[4-oxo-6-(pyrrolidin-4-yloxy)quinazolin-3(4H)-yl]benzamide (0.18 g), iodomethane (0.031 ml) and potassium carbonate (0.246 g) were stirred in DMA (1 ml) for 18 hours at room temperature. The reaction mixture was diluted with ethyl acetate and the organic phase was washed with water and concentrated. The residue was dissolved in ethyl acetate (2 ml) and triturated with iso-hexane and the resulting solid was filtered and dried under vacuum at 40° C. There was thus obtained the title compound (0.074 g); NMR Spectrum: (DMSOd6) 0.55 (m, 2H), 0.67 (m, 2H), 1.80 (m, 1H), 2.08 (m, 4H), 2.30 (m, 4H), 2.80 (m, 4H), 5.06 (s, 1H), 7.49 (m, 3H), 7.71 (d, 1H), 7.81 (s, 1H), 7.89 (d, 1H), 8.16 (s, 1H), 8.41 (s, 1H); Mass Spectrum: M+H+ 419.

Workup

  1. washthe organic phase was washed with water
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate (2 ml)
  4. customtriturated with iso-hexane
  5. filtrationthe resulting solid was filtered
  6. customdried under vacuum at 40° C

Sources & evidence

ORD record
ord-44c14fae6a3948d2b64a61519762c477
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

Loading…