Sodium Iodide → HCID 11384223, compound

HRID 2354199Notes

Reaction equation

HRID 2354199 reaction equation
[CH:1]1([NH:4][C:5](=[O:25])[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]([OH:24])[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:3][CH2:2]1.Cl.[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH:1]1([NH:4][C:5](=[O:25])[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][CH2:30][CH2:29][N:28]([CH3:32])[CH3:27])[CH:20]=4)[N:15]=[CH:14]3)[CH:7]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 11404895HCID 11404895, compoundHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 11384223HCID 11384223, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-Cyclopropyl-3-(6-hydroxy-4-oxoquinazolin-3 (4H)-yl)-4-methylbenzamide (0.15 g), 2-dimethylaminoethyl chloride hydrochloride (0.084 g), potassium carbonate (0.62 g), and sodium iodide (0.007 g) were stirred in acetone (9 ml) at 60° C. for 18 hours. The reaction mixture was filtered, the solids washed with acetone, and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with 2N NaOH solution, brine, dried (magnesium sulfate) and concentrated. Purification by column chromatography on a silica column eluting with 10% methanol/ethyl acetate+1% aqueous ammonia solution gave the title compound (0.159 g) as a white solid; NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.70 (m, 2H), 2.13 (s, 3H), 2.23 (s, 6H), 2.68 (t, 2H), 2.85 (m, 1H), 4.19 (t, 2H), 7.52 (m, 2H), 7.60 (s, 1H), 7.72 (d, 1H), 7.83 (s, 1H), 7.91 (d, 1H), 8.19 (s, 1H), 8.42 (d, 1H); Mass Spectrum: M+H+ 407.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe solids washed with acetone
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 2N NaOH solution, brine
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated
  8. customPurification by column chromatography on a silica column
  9. washeluting with 10% methanol/ethyl acetate+1% aqueous ammonia solution

Sources & evidence

ORD record
ord-bd9397144368450583c3ee88350daeee
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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