Aniline → N-[(S)-2-(3,4-Dichlorophenyl)-4-(phenylamino)butyl]-N-methyl-2-methoxy-3-cyano-1-naphthamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:29][CH:30]=O)[CH2:10][N:11]([CH3:28])[C:12]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]([C:24]#[N:25])[C:15]=2[O:26][CH3:27])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:29][CH2:30][NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:10][N:11]([CH3:28])[C:12]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]([C:24]#[N:25])[C:15]=2[O:26][CH3:27])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
3
Procedure
N-[(S)-2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methyl-2-methoxy-3-cyano-1-napthamide was reacted with aniline under standard reductive amination conditions to give the title compound which was converted to the citrate salt. 1H NMR (300 MHz, DMSO-d6) δ8.64-8.61 (m), 8.07-7.98 (m), 7.79-7.55 (m), 7.51-7.47 (m), 7.37-7.32 (t), 7.08-7.00 (m), 6.53-6.49 (m), 6.31-6.28 (d), 4.60-4.50 (t), 4.07-3.96 (m), 3.92 (s), 3.90-3.78 (m), 3.86 (s), 3.45-3.11 (m), 3.00-2.88 (m), 2.79 (s), 2.73 (s), 2.68 (s), 2.56-2.44 (m), 2.03-1.88 (m); MS APCI, m/z=532 (M+).
Sources & evidence
- ORD record
- ord-05d24bd977004d269fceda0bc884fe9e
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06586432B2
Reaction notes
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