Sodium Iodide → HCID 21936071, compound

HRID 1241575Notes

Reaction equation

HRID 1241575 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-acaef4cf846e4e3f8638a1cc499a7dd1
Source dataset
uspto-grants-2006_10
Patent number
US07115615B2

Reaction notes

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