Sodium Iodide → HCID 21936071, compound

HRID 1371480Notes

Reaction equation

HRID 1371480 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]4[O:22][CH2:23][O:24][C:17]=34)=[N:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:25][CH3:26].[I-].[Na+].[CH3:29][N:30]([CH:32]=O)C>C(#N)C>[N:30]1([CH2:2][CH2:3][O:4][C:5]2[CH:14]=[C:13]3[C:8]([C:9]([NH:15][C:16]4[CH:21]=[CH:20][CH:19]=[C:18]5[O:22][CH2:23][O:24][C:17]=45)=[N:10][CH:11]=[N:12]3)=[CH:7][C:6]=2[O:25][CH3:26])[CH2:32][CH2:7][CH2:6][CH2:5][CH2:14][CH2:29]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 21936037HCID 21936037, compound

Product 1

HCID 21936071HCID 21936071, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 7-(2-bromoethoxy)-4-(2,3-methylenedioxyanilino)-6-methoxyquinazoline (0.48 g) homopiperidine (0.322 ml), sodium iodide (0.002 g), DMF (5 ml) and acetonitrile (6 ml) was stirred and heated to 45° C. for 5 hours. The mixture was evaporated and the residue was partitioned between methylene chloride and water. The organic phase was washed with brine, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using a 19:1 mixture of methylene chloride and a saturated methanolic ammonia solution as eluent. The material so obtained was triturated under diethyl ether to give the title compound as a solid (0.4 g); NMR Spectrum: (DMSOd6 and CF3CO2D) 1.65 (m, 4H), 1.9 (m, 4H), 3.35 (m, 2H), 3.55 (m, 2H), 3.7 (m, 2H), 4.0 (s, 3H), 4.6 (m, 2H), 6.1 (s, 2H), 7.0 (m, 3H), 7.45 (s, 1H), 8.15 (s, 1H), 8.9 (s, 1H); Mass Spectrum: M+H+ 437.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between methylene chloride and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica using
  7. additiona 19:1 mixture of methylene chloride
  8. customThe material so obtained
  9. customwas triturated under diethyl ether

Sources & evidence

ORD record
ord-702ac0bd3b854bae95788684a2a9a3c5
Source dataset
uspto-grants-2007_01
Patent number
US07157467B2

Reaction notes

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