Acetic Anhydride → 6-{[(2S)-1-Acetylpyrrolidin-2-yl]methoxy}-4-(3-chloro-2-fluoroanilino)-7-methoxyquinazoline
Reaction equation
Cl.[Cl:2][C:3]1[C:4]([F:29])=[C:5]([CH:26]=[CH:27][CH:28]=1)[NH:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:24][CH3:25])=[C:14]([O:17][CH2:18][C@@H:19]3[CH2:23][CH2:22][CH2:21][NH:20]3)[CH:15]=2)[N:10]=[CH:9][N:8]=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>>[C:30]([N:20]1[CH2:21][CH2:22][CH2:23][C@H:19]1[CH2:18][O:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:24][CH3:25])[N:10]=[CH:9][N:8]=[C:7]2[NH:6][C:5]1[CH:26]=[CH:27][CH:28]=[C:3]([Cl:2])[C:4]=1[F:29])(=[O:32])[CH3:31]Participants
3
Procedure
Using a similar procedure to that described in Example 38, 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-[(2S)-pyrrolidin-2-ylmethoxy]quinazoline hydrochloride (300 mg; prepared as described in Example 31) was reacted with acetic anhydride to give the title product (280 mg, 92%); 1H NMR Spectrum: (DMSO d6) 1.89-2.05 (m, 6H); 2.15 (m, 1H); 3.43-3.56 (m, 2H); 3.93 (s, 3H); 4.00-4.11 (m, 1H); 4.17-4.21 (m, 1H); 4.32-4.42 (m, 1H); 7.19-7.29 (m, 2H); 7.41-7.54 (m, 2H); 7.79-7.82 (m, 1H); 8.36-8.37 (m, 1H); 9.52-9.55 (m, 1H); Mass Spectrum: (M+H)+ 445.
Sources & evidence
- ORD record
- ord-d39ac3d96a824797b7b52a5d1c14e637
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399667B2
Reaction notes
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