Hexahydrophthalic anhydride, cis- → racemic cis-2-{6-[(5-Methylpyridin-2-yl)methoxy]-1-[3-methyl-4-(trifluoromethoxy)benzyl]-1H-benzimidazol-2-yl}cyclohexanecarboxylic acid
Reaction equation
CC1C=C(CN)C=CC=1OC(F)(F)F.FC1C=C(C=CC=1[N+]([O-])=O)OCC1C=CC(C)=CN=1.[CH3:34][C:35]1[CH:36]=[C:37]([CH:56]=[CH:57][C:58]=1[O:59][C:60]([F:63])([F:62])[F:61])[CH2:38][NH:39][C:40]1[C:41]([NH2:55])=[CH:42][CH:43]=[C:44]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][N:49]=2)[CH:45]=1.[C:64]1(=[O:74])[C@@H:72]2[C@@H:67]([CH2:68][CH2:69][CH2:70][CH2:71]2)[C:66](=O)[O:65]1>>[CH3:54][C:51]1[CH:52]=[CH:53][C:48]([CH2:47][O:46][C:44]2[CH:43]=[CH:42][C:41]3[N:55]=[C:66]([C@H:67]4[CH2:68][CH2:69][CH2:70][CH2:71][C@H:72]4[C:64]([OH:74])=[O:65])[N:39]([CH2:38][C:37]4[CH:56]=[CH:57][C:58]([O:59][C:60]([F:62])([F:63])[F:61])=[C:35]([CH3:34])[CH:36]=4)[C:40]=3[CH:45]=2)=[N:49][CH:50]=1Participants
Reactant 4
Product 1
Procedure
The title compound was prepared using analogous conditions described in Example 92 using (3-methyl-4-(trifluoromethoxy)phenyl)methanamine and 2-((3-fluoro-4-nitrophenoxy)methyl)-5-methylpyridine in Step B and N1-(3-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, 553.22; m/z found, 554.0 [M+H]+. 1H NMR (300 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.34 (d, J=1.9, 1H), 7.56 (dd, J=7.8, 2.0, 1H), 7.45 (d, J=8.7, 1H), 7.33 (d, J=7.9, 1H), 7.21-7.19 (m, 2H), 7.08-6.97 (m, 2H), 6.83 (dd, J=8.7, 2.3, 1H), 5.49-5.33 (m, 2H), 5.08 (s, 2H), 3.73-3.64 (m, 1H), 2.75-2.64 (m, 1H), 2.27 (s, 3H), 2.19 (s, 3H), 1.90-1.41 (m, 6H), 1.33 (s, 2H).
Sources & evidence
- ORD record
- ord-b07a19d9a72b42238fa86d1a5f8d822e
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952177B2
Reaction notes
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