8-Iodonaphthalene-2-sulfonamide → N,N-Dibutyl-2-(4-(8-iodonaphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-1-methyl-1H-imidazole-4-carboxamide
Reaction equation
[CH2:1]([N:5]([CH2:35][CH2:36][CH2:37][CH3:38])[C:6]([C:8]1[N:9]=[C:10]([C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][C:15]=2[C:23]([N:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)=[O:24])[N:11]([CH3:13])[CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[I:39][C:40]1[CH:41]=[CH:42][CH:43]=[C:44]2[C:49]=1[CH:48]=[C:47]([S:50]([NH2:53])(=[O:52])=[O:51])[CH:46]=[CH:45]2>>[CH2:1]([N:5]([CH2:35][CH2:36][CH2:37][CH3:38])[C:6]([C:8]1[N:9]=[C:10]([C:14]2[CH:22]=[CH:21][C:17]([C:18](=[O:19])[NH:53][S:50]([C:47]3[CH:46]=[CH:45][C:44]4[C:49](=[C:40]([I:39])[CH:41]=[CH:42][CH:43]=4)[CH:48]=3)(=[O:51])=[O:52])=[CH:16][C:15]=2[C:23]([N:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)=[O:24])[N:11]([CH3:13])[CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4]Participants
Reactant 2
Product 1
Procedure
Following a procedure analogous to that for the synthesis of Example 265, 4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoic acid (Intermediate 264L, 45 mg, 0.09 mmol) and 8-iodonaphthalene-2-sulfonamide (Intermediate 6, 72 mg, 0.21 mmol) were converted to the title compound (11 mg, 15%). 1H NMR (CD3OD, 1:1 mixture of amide rotamers) δ 8.93 (s, 1H), 8.26 (d, J=7.2 Hz, 1H), 8.15 (dd, J=8.8, 1.6 Hz, 2H), 8.05-8.02 (m, 3H), 7.69 (dd, J=15.6, 8.0 Hz, 1H), 7.58 (s, 0.5H), 7.46 (br s, 0.5H), 7.40 (t, J=7.2 Hz, 1H), 7.23-7.11 (m, 3.5H), 6.91 (d, J=7.2 Hz, 0.5H), 4.76 (s, 1H), 4.45 (s, 1H), 3.73 (s, 3H), 3.63-3.52 (m, 6H), 2.82-2.78 (m, 2H), 1.56-1.46 (m, 2H), 1.45-1.27 (m, 4H), 1.20-1.00 (m, 2H), 1.00-0.92 (m, 3H), 0.85-0.75 (m, 3H); MS(ESI+) m/z 832.2 (M+H)+.
Sources & evidence
- ORD record
- ord-d6f4b05cbf614d84bb44a08718538e1e
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346795B2
Reaction notes
Loading…