N-butyl-4-(4-oxo-piperidin-1-yl)-benzenesulfonamide → N-Butyl-4-{4-[(2S)-3-(9H-carbazol-4-yloxy)-2-hydroxy-propylamino]-piperidin-1-yl}-benzenesulfonamide
Reaction equation
[NH2:1][CH2:2][CH:3]([OH:19])[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[CH2:20]([NH:24][S:25]([C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH2:39][CH2:38][C:37](=O)[CH2:36][CH2:35]2)=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH2:21][CH2:22][CH3:23]>>[CH2:20]([NH:24][S:25]([C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH2:39][CH2:38][CH:37]([NH:1][CH2:2][C@H:3]([OH:19])[CH2:4][O:5][C:6]3[C:18]4[C:17]5[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=5)[NH:11][C:10]=4[CH:9]=[CH:8][CH:7]=3)[CH2:36][CH2:35]2)=[CH:30][CH:29]=1)(=[O:26])=[O:27])[CH2:21][CH2:22][CH3:23]Participants
3
Procedure
The title compound was prepared from 1-amino-3-(9H-carbazol-4-yloxy)-propan-2-ol and Reference Example 11, N-butyl-4-(4-oxo-piperidin-1-yl)-benzenesulfonamide, according to the procedure of Example 1 as an off-white solid; mp 166-179° C.; 1H NMR (300 MHz, DMSO-d6) δ 0.79 (t, 3H), 1.15-1.40 (m, 6H), 1.75-1.90 (m, 2H), 2.64 (t, 2H), 2.60-3.00 (m, 5H), 3.60-4.20 (m, 5H), 6.69 (d, 1H), 6.80-7.60 (m, 7H), 7.90 (s, 1H), 8.20 (d, 2H), 11.35 (s, 1H); MS (ES) m/z: 551.1 (MH+); HRMS Calcd. for C30H39N4O4S (MH+): 551.2692. Found: 551.2664.
Sources & evidence
- ORD record
- ord-f2fe79e001f0446da81878fa78e2a8df
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06743787B2
Reaction notes
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