Potassium Iodide → HCID 10142294, compound

HRID 1371482Notes

Reaction equation

HRID 1371482 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH2:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[C:6]2[O:31][CH2:32][O:33][C:5]2=[CH:4][CH:3]=1.Cl[CH2:35][C:36]#[N:37].[I-].[K+].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:21][CH2:22][CH2:23][CH2:24][N:25]4[CH2:26][CH2:27][N:28]([CH2:35][C:36]#[N:37])[CH2:29][CH2:30]4)=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[C:6]2[O:31][CH2:32][O:33][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 21935995HCID 21935995, compound

Product 1

HCID 10142294HCID 10142294, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(6-chloro-2,3-methylenedioxyanilino)-6-methoxy-7-(3-piperazin-1-ylpropoxy)quinazoline (0.19 g), 2-chloroacetonitrile (0.038 ml), potassium iodide (0.020 g), potassium carbonate (0.139 g) and DMF (2.5 ml) was stirred at ambient temperature for 16 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was washed with water and with brine, dried over magnesium sulphate and evaporated. The crude product was purified by column chromatography on silica using a 93:7 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound (0.13 g) as a solid; NMR Spectrum: (DMSOd6 and CF3CO2D) 2.3 (m, 2H), 2.6 (m, 2H), 3.05 (m, 2H), 3.15 (m, 2H), 3.35 (m, 2H), 3.65 (m, 2H), 3.9 (s, 2H), 4.05 (s, 3H), 4.35 (m, 2H), 6.15 (s, 2H), 7.05 (d, 1H), 7.15 (d, 1H), 7.4 (s, 1H), 8.15 (s, 1H), 8.9 (s, 1H); Mass Spectrum: [M−H]− 509 and 511; Elemental Analysis: Found C, 58.41; H, 5.62; N, 15.93. C25H27ClN6O40.2H2O requires C, 58.35; H. 5.37; N, 16.33%.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with water and with brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe crude product was purified by column chromatography on silica using
  6. additiona 93:7 mixture of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-9099b02ac9af486983d523265ca2d607
Source dataset
uspto-grants-2007_01
Patent number
US07157467B2

Reaction notes

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