trans-Cyclohexane-1,2-dicarboxylic anhydride → racemic trans-2-(6-[(5-Methylpyridin-2-yl)methoxy]-1-{[4'-(trifluoromethyl)biphenyl-4-yl]methyl}-1H-benzimidazol-2-yl)cyclohexanecarboxylic acid
Reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)=[CH:20][CH:19]=3)[C:13]([NH2:34])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.[C:35]1(=[O:45])[C@H:43]2[C@@H:38]([CH2:39][CH2:40][CH2:41][CH2:42]2)[C:37](=O)[O:36]1>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]3[N:34]=[C:37]([C@@H:38]4[CH2:39][CH2:40][CH2:41][CH2:42][C@H:43]4[C:35]([OH:45])=[O:36])[N:16]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([C:24]5[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:26][CH:25]=5)=[CH:20][CH:19]=4)[C:14]=3[CH:15]=2)=[N:6][CH:7]=1Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared using analogous conditions described in Example 1 using 5-((5-methylpyridin-2-yl)methoxy)-N1-((4′-(trifluoromethyl)-[1,1′-biphenyl]-4-yl)methyl)benzene-1,2-diamine and racemic trans-hexahydroisobenzofuran-1,3-dione in Step C. MS (ESI): mass calcd. for C35H32F3N3O3, 599.2; m/z found, 600.2 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.27 (d, J=2.1, 1H), 7.76 (d, J=8.1, 2H), 7.69 (d, J=8.3, 2H), 7.65-7.58 (m, 2H), 7.58-7.46 (m, 2H), 7.42-7.22 (m, 3H), 6.97-6.90 (m, 2H), 5.53 (s, 2H), 5.09 (s, 2H), 3.19 (td, J=11.5, 3.6, 1H), 3.03 (td, J=11.3, 3.5, 1H), 2.23 (s, 3H), 2.21-2.17 (m, 1H), 1.89-1.79 (m, 1H), 1.77-1.59 (m, 2H), 1.58-1.19 (m, 4H).
Sources & evidence
- ORD record
- ord-80963505e1bd409d8ce963272fca3535
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952177B2
Reaction notes
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