4-[4-(Methanesulfonamido)phenyl]butyraldehyde → (2-(3,5-dimethylphenyl)-3-{2-[4-(4-methanesulfonylaminophenyl)butylamino]ethyl}-1H-indol-5-yl)acetic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=1)=[C:9]2[CH2:23][CH2:24][NH2:25])[CH3:2].[CH3:27][S:28]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][CH2:40][CH:41]=O)=[CH:34][CH:33]=1)(=[O:30])=[O:29]>>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([C:15]1[CH:16]=[C:17]([CH3:22])[CH:18]=[C:19]([CH3:21])[CH:20]=1)=[C:9]2[CH2:23][CH2:24][NH:25][CH2:41][CH2:40][CH2:39][CH2:38][C:35]1[CH:36]=[CH:37][C:32]([NH:31][S:28]([CH3:27])(=[O:30])=[O:29])=[CH:33][CH:34]=1)[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
The reductive amination reaction of [3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-acetic acid ethyl ester and 4-[4-(methanesulfonamido)phenyl]butyraldehyde was accomplished according to the procedure of Example 14.1, Step 14.1B to give the titled compound in 29% yield as a stiff foam; homogenous by TLC in 92.5:7.5 CH2Cl2 --MeOH. 500 MHz 1H NMR (CDCl3) was consistent with the assigned structure. Mass spectrum (ESI): m/e=576 (M+H).
Sources & evidence
- ORD record
- ord-e77fe59f53e9495f93415d80d5c5864b
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05756507
Reaction notes
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