3-Nitro-1-naphthoyl chloride → N-[(S)-2-(3,4-dichlorophenyl)-4-hydroxybutyl]-N-methyl-3-nitro-1-naphthamide
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14](Cl)=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].[Cl:17][C:18]1[CH:19]=[C:20]([C@H:25]([CH2:29][CH2:30][OH:31])[CH2:26][NH:27][CH3:28])[CH:21]=[CH:22][C:23]=1[Cl:24]>>[Cl:17][C:18]1[CH:19]=[C:20]([C@H:25]([CH2:29][CH2:30][OH:31])[CH2:26][N:27]([CH3:28])[C:14]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:15])[CH:21]=[CH:22][C:23]=1[Cl:24]Participants
3
Procedure
By the method of Example 3f, 3-nitro-1-naphthoyl chloride was reacted with (S)-2-(3,4-dichlorophenyl)-4-hydroxybutyl-N-methylamine to give N-[(S)-2-(3,4-dichlorophenyl)-4-hydroxybutyl]-N-methyl-3-nitro-1-naphthamide. This was reacted by the method of Example 3g to give the title compound: 1H NMR (300 MHz, CDCl3) δ 9.65 (s), 9.44 (s), 9.07-9.02 (m), 8.38-6.04 (m), 4.44-1.18 (m); MS APCI, m/z=445 (M+).
Sources & evidence
- ORD record
- ord-3de5708044c24f74a09c62e5a12ccf08
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06365602B1
Reaction notes
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