Ethyl (S)-2-(trifluoromethylsulfonyloxy)propionate → n-({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-n-(2-methoxyethyl)-d-alanine
Reaction equation
[Cl:1][C:2]1[C:3]([F:27])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:25][CH3:26])=[C:16]([CH2:19][NH:20][CH2:21][CH2:22][O:23][CH3:24])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.CC[O:30][C:31]([C@@H:33](OS(C(F)(F)F)(=O)=O)[CH3:34])=[O:32]>>[Cl:1][C:2]1[C:3]([F:27])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:25][CH3:26])=[C:16]([CH2:19][N:20]([CH2:21][CH2:22][O:23][CH3:24])[C@@H:33]([C:31]([OH:32])=[O:30])[CH3:34])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1Participants
3
Procedure
N-(3-Chloro-2-fluorophenyl)-7-methoxy-6-{[(2-methoxyethyl)amino]methyl}quinazolin-4-amine (prepared as described in Example 50) was coupled with ethyl O-trifluoromethanesulfonyl-L-lactate and hydrolysed using analogous methods to those described for the equivalent steps in Example 46 to give N-({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)-N-(2-methoxyethyl)-D-alanine; 1H NMR Spectrum: (DMSO-d6) 1.28 (d, 3H); 2.85 (t, 2H); 3.13 (s, 3H); 3.34 (m, 2H); 3.56 (q, 1H); 3.93 (m, 5H); 7.18 (s, 1H); 7.28 (t, 1H); 7.48 (t, 1H); 7.57 (m, 1H); 8.41 (m, 2H); 9.70 (brs, 1H); Mass Spectrum: (M+H)+ 463.
Sources & evidence
- ORD record
- ord-63e12d393c6d42cc9a2fb120a2a1e43f
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07632840B2
Reaction notes
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