Potassium Iodide → HCID 71029076, compound

HRID 1879950Notes

Reaction equation

HRID 1879950 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][C:23]=2[O:24][CH3:25])[N:20]=[CH:19][N:18]=[C:17]3[NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=2[F:34])[CH2:9][CH2:8]1)=[O:6].[NH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1.[I-].[K+]>CC(N(C)C)=O>[Cl:33][C:29]1[C:28]([F:34])=[C:27]([CH:32]=[CH:31][CH:30]=1)[NH:26][C:17]1[C:16]2[C:21](=[CH:22][C:23]([O:24][CH3:25])=[C:14]([O:13][CH:10]3[CH2:9][CH2:8][N:7]([C:5](=[O:6])[NH:4][CH2:3][CH2:2][N:35]4[CH2:39][CH2:38][CH:37]=[CH:36]4)[CH2:12][CH2:11]3)[CH:15]=2)[N:20]=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 31268PyrrolidineHCID 69230623HCID 69230623, compound

Product 1

HCID 71029076HCID 71029076, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-{[1-(N-(2-chloroethyl)carbamoyl)piperidin-4-yl]oxy}-4-(3-chloro-2-fluoroanilino)-7-methoxyquinazoline (204 mg, 0.4 mmol), pyrrolidine (0.14 ml, 1.6 mmol) and potassium iodide (134 mg, 0.8 mmol) in dimethylacetamide (3 ml) was heated at 80° C. for 4 hours. After cooling and evaporation of the solvents under vacuum, the residue was partitioned in water, dichloromethane and extracted with dichloromethane. The organic layer was washed with water and brine, and dried over magnesium sulfate. After evaporation of the solvents under vacuum, the residue was purified by chromatography on silica gel (eluant: 3% to 4% 7N methanolic ammonia in dichloromethane) to give the title compound as a white solid (77 mg, 36%).

Workup

  1. temperatureAfter cooling
  2. customevaporation of the solvents under vacuum
  3. customthe residue was partitioned in water
  4. extractiondichloromethane and extracted with dichloromethane
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customAfter evaporation of the solvents under vacuum
  8. customthe residue was purified by chromatography on silica gel (eluant: 3% to 4% 7N methanolic ammonia in dichloromethane)

Sources & evidence

ORD record
ord-b6635f996c684ffd841ead5978931300
Source dataset
uspto-grants-2012_11
Patent number
US08318752B2

Reaction notes

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