8-Iodonaphthalene-2-sulfonamide → 2-(2-((S)-3-(Azidomethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(8-iodonaphthalen-2-ylsulfonylcarbamoyl)phenyl)-N,N-dibutyl-1-methyl-1H-imidazole-4-carboxamide
Reaction equation
[N:1]([CH2:4][C@@H:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][N:6]1[C:15]([C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[C:26]1[N:27]([CH3:42])[CH:28]=[C:29]([C:31](=[O:41])[N:32]([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH2:35][CH3:36])[N:30]=1)[C:20](O)=[O:21])=[O:16])=[N+:2]=[N-:3].[I:43][C:44]1[CH:45]=[CH:46][CH:47]=[C:48]2[C:53]=1[CH:52]=[C:51]([S:54]([NH2:57])(=[O:56])=[O:55])[CH:50]=[CH:49]2>>[N:1]([CH2:4][C@@H:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][N:6]1[C:15]([C:17]1[CH:18]=[C:19]([C:20](=[O:21])[NH:57][S:54]([C:51]2[CH:50]=[CH:49][C:48]3[C:53](=[C:44]([I:43])[CH:45]=[CH:46][CH:47]=3)[CH:52]=2)(=[O:56])=[O:55])[CH:23]=[CH:24][C:25]=1[C:26]1[N:27]([CH3:42])[CH:28]=[C:29]([C:31]([N:32]([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:37][CH2:38][CH2:39][CH3:40])=[O:41])[N:30]=1)=[O:16])=[N+:2]=[N-:3]Participants
3
Reactant 2
Product 1
Procedure
Following a procedure analogous to that for the synthesis of Example 271, 3-((S)-3-(azidomethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)benzoic acid (Intermediate 281D, 120 mg, 0.21 mmol) and 8-iodonaphthalene-2-sulfonamide (Intermediate 8, 139 mg, 0.42 mmol) were converted to the title compound (76 mg, 41%). MS(ESI−) m/z 885.8 (M−H)−.
Sources & evidence
- ORD record
- ord-600c50407ca2481e8d352e14fc7e750e
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346795B2
Reaction notes
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