Hexahydrophthalic anhydride, cis- → racemic cis-2-{6-[(5-Methylpyridin-2-yl)methoxy]-1-[2-methyl-4-(trifluoromethoxy)benzyl]-1H-benzimidazol-2-yl}cyclohexanecarboxylic acid
Reaction equation
FC1C=C(C=CC=1[N+]([O-])=O)OCC1C=CC(C)=CN=1.[CH3:20][C:21]1[CH:44]=[C:43]([O:45][C:46]([F:49])([F:48])[F:47])[CH:42]=[CH:41][C:22]=1[CH2:23][NH:24][C:25]1[C:26]([NH2:40])=[CH:27][CH:28]=[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][N:34]=2)[CH:30]=1.[C:50]1(=[O:60])[C@@H:58]2[C@@H:53]([CH2:54][CH2:55][CH2:56][CH2:57]2)[C:52](=O)[O:51]1>>[CH3:39][C:36]1[CH:37]=[CH:38][C:33]([CH2:32][O:31][C:29]2[CH:28]=[CH:27][C:26]3[N:40]=[C:52]([C@H:53]4[CH2:54][CH2:55][CH2:56][CH2:57][C@H:58]4[C:50]([OH:60])=[O:51])[N:24]([CH2:23][C:22]4[CH:41]=[CH:42][C:43]([O:45][C:46]([F:48])([F:49])[F:47])=[CH:44][C:21]=4[CH3:20])[C:25]=3[CH:30]=2)=[N:34][CH:35]=1Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared using analogous conditions described in Example 92 using 2-((3-fluoro-4-nitrophenoxy)methyl)-5-methylpyridine in Step B and N1-(2-methyl-4-(trifluoromethoxy)benzyl)-5-((5-methylpyridin-2-yl)methoxy)benzene-1,2-diamine and cis-hexahydroisobenzofuran-1,3-dione in Step D. MS (ESI): mass calcd. for C30H30F3N3O4, 553.20; m/z found, 553.9 [M+H]+. 1H NMR (300 MHz, DMSO-d6) δ 8.34 (s, 1H), 7.66 (s, 1H), 7.60 (d, J=7.3, 1H), 7.37 (d, J=8.2, 1H), 7.32 (s, 1H), 7.15 (s, 2H), 6.95 (d, J=7.9, 1H), 6.36 (d, J=8.3, 1H), 5.60 (s, 2H), 5.11 (s, 2H), 3.59 (s, 1H), 2.71 (s, 1H), 2.50 (s, 3H), 2.28 (s, 3H), 1.75 (brs, 4H), 1.60-1.30 (m, 4H).
Sources & evidence
- ORD record
- ord-1902f677b4d248439a6627ac6e8951f4
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952177B2
Reaction notes
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