Ethyl bromoacetate → HCID 21701552, compound

HRID 1596288Notes

Reaction equation

[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=[C:4]([F:22])[CH:3]=1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1.O>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=[C:4]([F:22])[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (3.0 g, 9 mmol), (prepared as described for the starting material in Example 4), ethyl bromoacetate (1.11 ml, 10 mmol) and potassium carbonate (2.84 g, 20.6 mmol) in NMP (60 ml) was heated at 90° C. for 3 hours. The mixture was allowed to cool, diluted with water and extracted with ethyl acetate. The combined extracts were washed with water, dried (MgSO4) and concentrated by evaporation. Hexane was added, the mixture was cooled and the precipitated solid was collected by filtration to give 4-(4-chloro-2-fluoroanilino)-7-(ethoxycarbonylmethoxy)-6-methoxyquinazoline (1.75 g, 48%).

Workup

custom(prepared
temperatureto cool
extractionextracted with ethyl acetate
washThe combined extracts were washed with water
dry with materialdried (MgSO4)
concentrationconcentrated by evaporation
additionHexane was added
temperaturethe mixture was cooled
filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record: ord-f9182b6c81a74287adb1e2146276ec10
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291455B1

Reaction notes

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