Potassium Carbonate → HCID 178493970, compound

HRID 1596255Notes

Reaction equation

HRID 1596255 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[Cl:11][C:12]1[CH:31]=[CH:30][C:15]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([OH:29])=[C:24](OC)[CH:25]=3)[N:20]=[CH:19][N:18]=2)=[C:14]([F:32])[CH:13]=1.[C:33](=O)([O-])[O-:34].[K+].[K+]>CN(C=O)C>[ClH:2].[Cl:11][C:12]1[CH:31]=[CH:30][C:15]([NH:16][C:17]2([O:34][CH3:33])[C:26]3[C:21](=[CH:22][C:23]([O:29][CH2:3][CH2:4][N:5]4[CH2:10][CH2:9][O:8][CH2:7][CH2:6]4)=[CH:24][CH:25]=3)[N:20]=[CH:19][NH:18]2)=[C:14]([F:32])[CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 1355137204-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline

Product 1

HCID 178493970HCID 178493970, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-(2-Chloroethyl)morpholine hydrochloride (40 mg, 2.1 mmol) was added to 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (63 mg, 0.2 mmol), (prepared as described for the starting material in Example 4), and potassium carbonate (95 mg, 0.69 mmol) in DMF (3 ml) and the mixture heated at 100° C. for 3 hours. The mixture was allowed to cool, the volatiles were removed by evaporation and the residues partitioned between water and methylene chloride. The organic phase was separated, passed through phase separating paper and the solvent was removed by evaporation. The residue was dissolved in acetone, and hydrogen chloride in ether (0.2 ml of a 1M solution, 0.2 mmol) was added. The precipitated product was collected by filtration and dried to give 4-(4-chloro-2-fluoroanilino)4-methoxy-7-(2-morpholinoethoxy)quinazoline hydrochloride (50 mg, 50%).

Workup

  1. custom(prepared
  2. temperatureto cool
  3. customthe volatiles were removed by evaporation
  4. customthe residues partitioned between water and methylene chloride
  5. customThe organic phase was separated
  6. customseparating paper
  7. customthe solvent was removed by evaporation
  8. dissolutionThe residue was dissolved in acetone
  9. additionhydrogen chloride in ether (0.2 ml of a 1M solution, 0.2 mmol) was added
  10. filtrationThe precipitated product was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-dace3535399a4a6995186f8106b026a8
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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