Sodium ethoxide → [4-(Dimethylamino)-2-ethoxy-3-phenylquinolin-6-yl](1-methyl-1H-imidazol-5-yl)pyridin-4-ylmethanol.TFA
Reaction equation
Cl[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([N:18]([CH3:20])[CH3:19])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:21]([C:29]3[N:33]([CH3:34])[CH:32]=[N:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[OH:22])[CH:8]=2)[N:3]=1.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36].CC[O-].[Na+].C[O-].[Na+]>CCO.CO>[CH3:19][N:18]([CH3:20])[C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:21]([C:29]3[N:33]([CH3:34])[CH:32]=[N:31][CH:30]=3)([C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)[OH:22])[CH:8]=2)[N:3]=[C:2]([O:36][CH2:35][CH3:37])[C:11]=1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
The title compound was prepared using (2-chloro-4-(dimethylamino)-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)(pyridin-4-yl)methanol (Example 47) and NaOEt in EtOH in place of (3-chlorophenyl)(2,4-dichloro-3-phenylquinolin-6-yl)(pyridin-3-yl)methanol and NaOMe in MeOH, respectively, according to the procedure described in Example 79. 1H NMR (400 MHz, MeOH-d4) δ 9.07 (s, 1H), 8.82 (d, J=5.62 Hz, 2H), 8.09 (s, 1H), 7.99 (d, J=5.38 Hz, 2H), 7.87 (d, J=8.56 Hz, 1H), 7.63 (dd, J=1.96, 8.56 Hz, 1H), 7.41-7.48 (m, 2H), 7.39 (d, J=7.09 Hz, 1H), 7.24 (d, J=7.82 Hz, 2H), 7.17 (s, 1H), 4.42 (q, J=7.01 Hz, 2H), 3.72 (s, 3H), 2.57 (s, 6H), 1.24 (t, J=6.97, 3H); MS m/e 480.3 [M+H]+.
Sources & evidence
- ORD record
- ord-40195600afd44a0aa8dc70435d5bf0e4
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309222B2
Reaction notes
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