Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=2)[N:10]=[C:9]1[CH3:20].[N:21]1[C:26]([CH:27]=[O:28])=[CH:25][CH:24]=[CH:23][C:22]=1C=O.O.O1CCOC[CH2:33]1>C(OC(=O)C)(=O)C.[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=2)[N:10]=[C:9]1[CH:20]=[CH:33][C:26]1([CH:27]=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][NH:21]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A catalytic amount (about 100 mg) of anhydrous zinc chloride was added to a solution of 576 mg (2.0 mmol) of 3-(2-chlorophenyl)-6-fluoro-2-methyl-4(3H)-quinazolinone and 270 mg (2.0 mmol) of 2,6-pyridinedicarboxaldehyde in 20-25 mL of dioxane and 1.0 mL of acetic anhydride. The reaction mixture was heated at reflux under a nitrogen atmosphere for 3 hours until TLC indicated that the starting materials had been consumed. The cooled reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The combined extracts were dried with brine and magnesium sulfate, treated with decolonizing carbon and filtered and the solvent was removed to give the desired product. This was taken up in 2:1 ether/pentane and the crystals were filtered to give 266 mg of the product, 33%, m.p. 247-248° C.
Workup
- temperatureThe reaction mixture was heated
- temperatureat reflux under a nitrogen atmosphere for 3 hours until TLC
- customhad been consumed
- customThe cooled reaction mixture
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe combined extracts were dried with brine and magnesium sulfate
- additiontreated with decolonizing carbon
- filtrationfiltered
- customthe solvent was removed
Sources & evidence
- ORD record
- ord-e414f10c31ef4c24873d9551f513cbb0
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06380204B1
Linked notes
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