Pyridine → HCID 86759734, compound

HRID 2182537Notes

Reaction equation

[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].ClN([C:25]1[C:34]2[C:29](=[CH:30][C:31](O)=[C:32]([O:35][CH3:36])[CH:33]=2)[N:28]=[CH:27][N:26]=1)C1C=CC=CC=1F.N1C=CC=CC=1>C(Cl)Cl>[CH3:36][O:35][C:32]1[CH:33]=[C:34]2[C:29](=[CH:30][C:31]=1[O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[N:28]=[CH:27][N:26]=[CH:25]2

Participants

Conditions

Temperature: 0 °C

Procedure

Trifluoromethanesulphonic anhydride (0.55 ml, 3.3 mmol) was added to a stirred suspension of 4-(chloro-2-fluoroanilino)7-hydroxy-6-methoxyquinazoline (959 mg, 3 mmol), (prepared as described for the starting material in Example 2), in methylene chloride (2.2 ml) and pyridine (2.2 ml) under argon at 0° C. Thee reaction mixture was stirred for 1 hour at 0° C. allowed to warm to ambient temperature and stirred for a further 1.5 hours. The volatiles were removed by evaporation, the residue was dissolved in ethyl acetate, washed with dilute hydrochloric acid and brine, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with ether/petroleum ether to give 444-chloro-2-fluoroanilino)6-methoxy-7-(trifluoromethylsulphonyloxy)quinazoline (270 mg, 60%) as a beige solid.

Workup

custom(prepared
customat 0° C
temperatureto warm to ambient temperature
stirringstirred for a further 1.5 hours
customThe volatiles were removed by evaporation
dissolutionthe residue was dissolved in ethyl acetate
washwashed with dilute hydrochloric acid and brine
dry with materialdried (MgSO4)
customthe solvent removed by evaporation
customThe residue was triturated with ether/petroleum ether

Sources & evidence

ORD record: ord-53ca47b103c0481c9133fed8cfb1c738
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06897210B2

Reaction notes

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