Hexahydrophthalic anhydride, cis- → racemic cis-2-(5-(Benzo[d]thiazol-2-ylmethoxy)-1-(4-(piperidin-1-yl)benzyl)-1H-benzo[d]imidazol-2-yl)cyclohexanecarboxylic acid
Reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][NH2:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.F[C:16]1[CH:32]=[CH:31][C:19]([O:20][CH2:21][C:22]2[S:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[N:26]=2)=[CH:18][C:17]=1[N+:33]([O-])=O.[C@@H:36]12[C:45](=O)[O:44][C:42](=[O:43])[C@@H:37]1[CH2:38][CH2:39][CH2:40][CH2:41]2>>[S:23]1[C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=[C:22]1[CH2:21][O:20][C:19]1[CH:31]=[CH:32][C:16]2[N:14]([CH2:13][C:10]3[CH:11]=[CH:12][C:7]([N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:8][CH:9]=3)[C:45]([C@H:36]3[CH2:41][CH2:40][CH2:39][CH2:38][C@H:37]3[C:42]([OH:44])=[O:43])=[N:33][C:17]=2[CH:18]=1Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared using analogous conditions described in Example 208 using (4-(piperidin-1-yl)phenyl)methanamine and 2-((4-fluoro-3-nitrophenoxy)methyl)benzo[d]thiazole in step B and cis-1,2-cyclohexanedicarboxylic anhydride in step D using conventional heating. MS (ESI): mass calcd. for C34H36N4O3S, 580.76; m/z found, 581.3 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.21 (s, 1H), 7.99-7.94 (m, 2H), 7.55-7.48 (m, 1H), 7.45-7.39 (m, 1H), 7.34-7.28 (m, 2H), 7.04 (dd, J=8.9, 2.4 Hz, 2H), 6.92-6.87 (m, 2H), 5.54 (s, 2H), 5.45 (d, J=16.6 Hz, 1H), 5.38 (d, J=16.6 Hz, 1H), 3.59-3.51 (m, 1H), 3.11-3.04 (m, 4H), 2.89-2.82 (m, 1H), 2.38-2.26 (m, 1H), 2.10-1.99 (m, 1H), 1.86-1.70 (m, 4H), 1.70-1.60 (m, 4H), 1.60-1.35 (m, 4H).
Sources & evidence
- ORD record
- ord-b6f81109dba845fdb0197c30493597aa
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067917B2
Reaction notes
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