Acetyl bromide → N-acetyl-2-chloro-5-[(4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidin-1-yl)carbonyl]benzene-sulfonamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][C:13]([CH2:22][CH2:23][N:24]3[CH:29]4[CH2:30][CH2:31][CH:25]3[CH2:26][CH:27]([N:32]3[C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=5[N:34]=[C:33]3[CH3:41])[CH2:28]4)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[S:42]([NH2:45])(=[O:44])=[O:43].[C:46](Br)(=[O:48])[CH3:47]>>[C:46]([NH:45][S:42]([C:3]1[CH:4]=[C:5]([C:8]([N:10]2[CH2:11][CH2:12][C:13]([CH2:22][CH2:23][N:24]3[CH:29]4[CH2:30][CH2:31][CH:25]3[CH2:26][CH:27]([N:32]3[C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=5[N:34]=[C:33]3[CH3:41])[CH2:28]4)([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:14][CH2:15]2)=[O:9])[CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:43])=[O:44])(=[O:48])[CH3:47]Participants
Reactant 2
Product 1
Procedure
N-acetyl-2-chloro-5-[(4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidin-1-yl)carbonyl]benzene-sulfonamide (21.8 mg, quant.) was obtained as amorphous solid from 2-chloro-5-[(4-{2-[3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidin-1-yl)carbonyl]benzenesulfonamide and acetyl bromide following the procedure outlined in example 476. 1H NMR (300 MHz, DMSO-d6) 87.85-7.50 (m, 3H), 7.49 (d, J=8.5 Hz, 1H), 7.41-7.35 (m, 5H), 7.25-7.21 (m, 1H), 7.15-7.09 (m, 2H), 4.54 (br, 1H), 3.96 (br, 1H), 3.42-3.29 (m, 5H), 3.06-3.03 (m, 1H), 2.45-2.36 (m, 5H), 2.17-2.07 (m, 2H), 1.98-1.75 (m, 10H), 1.71-1.70 (m, 3H), 1.63-1.61 (m, 2H). HRMS m/z (M+H)+ calcd: 688.2724, obsd: 688.2745.
Sources & evidence
- ORD record
- ord-fe5378b952ca4702bb239c66411c8aab
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07645771B2
Reaction notes
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