4-Nitro-5,6,7,8-tetrahydro-1-naphthalenecarbonyl chloride → N-[(S)-2-(3,4-Dichlorophenyl)4-[4-[(S)-2-methylsulfinylphenyl]-1-piperidinyl]butyl]-N-methyl-4-nitro-5,6,7,8-tetrahydro-1-naphthamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S@:27]([CH3:29])=[O:28])[CH2:17][CH2:16]2)[CH2:10][NH:11][CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[N+:30]([C:33]1[C:42]2[CH2:41][CH2:40][CH2:39][CH2:38][C:37]=2[C:36]([C:43](Cl)=[O:44])=[CH:35][CH:34]=1)([O-:32])=[O:31]>>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S@:27]([CH3:29])=[O:28])[CH2:19][CH2:20]2)[CH2:10][N:11]([CH3:12])[C:43]([C:36]2[C:37]3[CH2:38][CH2:39][CH2:40][CH2:41][C:42]=3[C:33]([N+:30]([O-:32])=[O:31])=[CH:34][CH:35]=2)=[O:44])[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
3
Reactant 2
Product 1
Procedure
Using a procedure analogous to that described in Example 3, N-[(S)-2-(3,4-dichlorophenyl)4-[4-[(S)-2-methylsulfinylphenyl]-1-piperidinyl]butyl]-N-methylamine was reacted with 4-nitro-5,6,7,8-tetrahydro-1-naphthalenecarbonyl chloride [prepared from 4-nitro-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (T. Nakayama, T. Okutome, R. Matsui, M. Kurumi, Y. Sakurai, T. Aoyama, S. Fujii, Chem. Pharm. Bull. 32(10) 3968 (1984))] and the product was converted to the citrate salt MS: m/z 656 (M+H). Analysis for C34H39Cl2N3O4S.C6H8O7.1.0H2O: calculated: C, 54.42; H, 5.70; N, 4.85. found: C, 55.03; H, 5.55; N, 4.94.
Sources & evidence
- ORD record
- ord-7eb94af1736d4407901e5a81edf156c0
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06403601B1
Reaction notes
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