Reaction equation
N1C2C(=CC=CC=2)C=NC=1.[Cl:11][C:12]1[CH:13]=[C:14]([C:16]([F:20])=[CH:17][C:18]=1[Cl:19])[NH2:15].Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([F:35])=[C:29]([N+:32]([O-:34])=[O:33])[CH:30]=2)[N:25]=[CH:24][N:23]=1>>[Cl:11][C:12]1[CH:13]=[C:14]([NH:15][C:22]2[C:31]3[C:26](=[CH:27][C:28]([F:35])=[C:29]([N+:32]([O-:34])=[O:33])[CH:30]=3)[N:25]=[CH:24][N:23]=2)[C:16]([F:20])=[CH:17][C:18]=1[Cl:19]Participants
Procedure
In another particular, which includes a quinazoline that is substituted by two different reactive groups at positions 6 and 7 thereof, 3,4-dichloro-6-fluoroaniline is reacted with 4-chloro-7-fluoro-6-nitroquinazoline, so as to produce 4-[(3,4-dichloro-6-fluorophenyl)amino]-7-fluoro-6-nitroquinazoline. The 4-[(3,4-dichloro-6-fluorophenyl)amino]-7-fluoro-6-nitroquinazoline is then reacted with a sodium salt of 3-(4-morpholinyl-1-propanol), so as to produce 4-[(3,4-dichloro-6-fluoro-phenyl)amino]-7-[3-(4-morpholinyl)propoxy]-6-nitroquinazoline, which is reduced, by means of an ethanolic solution of hydrazine hydrate and Raney®Nickel, so as to produce 6-amino-4-[(3,4-dichloro-6-fluorophenyl)amino]-7-[3-(4-morpholinyl)propoxy]quinazoline. The product is then reacted with a carbon-11 labeled acryloyl chloride so as to produce a carbon-11 labeled N-{4-[(3,4-dichloro-6-fluorophenyl)amino]-7-[3-(4-morpholinyl)propoxy]quinazoline-6-yl}acrylamide (carbon-11 labeled morpholino-substituted Compound 3).
Sources & evidence
- ORD record
- ord-66fb621122b84a2b986c4ce07a4fd5a3
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07172749B2
Linked notes
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