Hydrochloric Acid → 7-(3-Carboxypropoxy)-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline

HRID 547200Notes

Reaction equation

[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]CC)=[O:24])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=[C:4]([F:30])[CH:3]=1.O.CO.Cl>[OH-].[Na+]>[C:23]([CH2:22][CH2:21][CH2:20][O:19][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([NH:6][C:5]3[CH:28]=[CH:29][C:2]([Cl:1])=[CH:3][C:4]=3[F:30])=[N:8][CH:9]=[N:10]2)=[CH:15][C:14]=1[O:17][CH3:18])([OH:25])=[O:24]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 4-(4-chloro2-fluoroanilino)-7-(3-ethoxycarbonylpropoxy)6-methoxyquinazoline (220 mg, 0.5 mmol) in aqueous sodium hydroxide solution (4 ml of a 2M solution, 8 mmol), water (2 ml) and methanol (0.5 ml) was stirred and heated at 40° C. for 3 hours. The mixture was allowed to cool and was then acidified with 2M hydrochloric acid. The resulting white precipitate was collected by filtration and washed with acetone and water to give 7-(3carboxypropoxy)-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline (170 mg, 83%).

Workup

temperatureto cool
filtrationThe resulting white precipitate was collected by filtration
washwashed with acetone and water

Sources & evidence

ORD record: ord-7ee6cccd803c471dbaa773c8c2f10b95
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE042353E1

Reaction notes

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