Isobutyryl chloride → 2-Chloro-N-isobutyryl-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](Cl)(=[O:50])[CH:47]([CH3:49])[CH3:48]>>[Cl:1][C:2]1[CH:7]=[CH:6][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:4][C:3]=1[S:42]([NH:45][C:46](=[O:50])[CH:47]([CH3:49])[CH3:48])(=[O:43])=[O:44]Participants
3
Reactant 2
Product 1
Procedure
2-Chloro-N-isobutyryl-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 (19 mg, 80%) 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 isobutyryl chloride following the procedure outlined in example 476. 1H NMR (300 MHz, DMSO-d6, 100° C.) δ 7.85-7.76 (m, 2H), 7.60-7.50 (m, 2H), 7.42-7.28 (m, 5H), 7.26 (m, 1H), 7.18-7.12 (m, 2H), 4.76 (br, 1H), 3.36-3.08 (m, 7H), 2.53-2.27 (m, 7H), 2.04-1.82 (m, 10H), 1.69 (d, J=7.6 Hz, 2H), 0.95 (d, J=6.6 Hz, 6H). HRMS m/z (M+H)+ calcd: 716.3037, obsd: 716.3013.
Sources & evidence
- ORD record
- ord-a5efda27d0fe455694d8769337678ab2
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07645771B2
Reaction notes
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