Sodium Iodide → HCID 22140831, compound

HRID 641775Notes

Reaction equation

HRID 641775 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:26][CH2:27][CH2:28][CH2:29][N:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)=[CH:16][C:17]=3[O:19][CH:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[N:12]=[CH:11][N:10]=2)=[C:6]2[O:36][CH2:37][O:38][C:5]2=[CH:4][CH:3]=1.Cl[CH2:40][C:41]#[N:42].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:7]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:26][CH2:27][CH2:28][CH2:29][N:30]4[CH2:31][CH2:32][N:33]([CH2:40][C:41]#[N:42])[CH2:34][CH2:35]4)=[CH:16][C:17]=3[O:19][CH:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[N:12]=[CH:11][N:10]=2)=[C:6]2[O:36][CH2:37][O:38][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 22140783HCID 22140783, compound

Product 1

HCID 22140831HCID 22140831, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(6-chloro-2,3-methylenedioxyanilino)-7-(3-piperazin-1-ylpropoxy)-5-tetrahydropyran-4-yloxyquinazoline (1.3 g), 2-chloroacetonitrile (0.167 ml), sodium iodide (0.036 g), potassium carbonate (0.331 g) and DMF (15 ml) was stirred at ambient temperature for 5 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate 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 10:9:1 mixture of ethyl acetate, methylene chloride and methanol as eluent. There was thus obtained the title compound (0.69 g); NMR Spectrum: (CDCl3) 1.85-2.0 (m, 4H), 2.1 (m, 2H), 2.4-2.5 (m, 6H), 2.5-2.6 (m, 4H), 3.42 (s, 2H), 3.5-3.6 (m, 2H), 3.9-4.0 (m, 2H), 4.0-4.1 (m, 2H), 4.7 (m, 1H), 6.0 (s, 2H), 6.42 (s, 1H), 6.65 (d, 1H), 6.78 (d, 1H), 6.9 (d, 1H), 8.42 (s, 1H), 9.2 (s, 1H); Mass Spectrum: M+H+ 581 and 583.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate 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 10:9:1 mixture of ethyl acetate, methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-193bf452911a4c8ca8e0f9f0f53e9f0a
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

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