4-(4-Bromo-2-fluorophenoxy)-7-(3-(N-tertbutoxycarbonylamino)propoxy)-6-methoxyquinazoline → 7-(3-Aminopropoxy)-4-(4-bromo-2-fluorophenoxy)-6-methoxyquinazoline

HRID 454124Notes

Reaction equation

[Br:1][C:2]1[CH:32]=[CH:31][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH2:22][NH:23]C(OC(C)(C)C)=O)=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=[C:4]([F:33])[CH:3]=1>FC(F)(F)C(O)=O>[NH2:23][CH2:22][CH2:21][CH2:20][O:19][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([O:6][C:5]3[CH:31]=[CH:32][C:2]([Br:1])=[CH:3][C:4]=3[F:33])=[N:8][CH:9]=[N:10]2)=[CH:15][C:14]=1[O:17][CH3:18]

Participants

Conditions

Temperature: 85 °C

Procedure

4-(4-Bromo-2-fluorophenoxy)-7-(3-(N-tertbutoxycarbonylamino)propoxy)-6-methoxyquinazoline (5.46 g, 10.5 mmol) was taken up in trifluoroacetic acid (75 ml) and heated at 85° C. for 1.5 hours. The solution was allowed to cool and the excess trifluoroacetic acid removed by evaporation. The residue was then treated with aqueous ammonia (0.88) solution, extracted with dichloromethane (3×150 ml) and filtered through phase separating paper. The solvent was removed by evaporation to give 7-(3-aminopropoxy)-4-(4-bromo-2-fluorophenoxy)-6-methoxyquinazoline (4.42 g, 100%).

Workup

temperatureto cool
customthe excess trifluoroacetic acid removed by evaporation
additionThe residue was then treated with aqueous ammonia (0.88) solution
extractionextracted with dichloromethane (3×150 ml)
filtrationfiltered through phase
customseparating paper
customThe solvent was removed by evaporation

Sources & evidence

ORD record: ord-a449cf6d1b0c410bb92e1addb03650b0
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492560B2

Reaction notes

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