Hexahydrophthalic anhydride, cis- → racemic cis-2-{6-[(1-Methyl-1H-pyrazol-3-yl)methoxy]-1-[2-methyl-4-(trifluoromethoxy)benzyl]-1H-benzimidazol-2-yl}cyclohexanecarboxylic acid

HRID 1848731Notes

Reaction equation

HRID 1848731 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][C:18]=3[CH3:28])[C:12]([NH2:29])=[CH:11][CH:10]=2)=[N:3]1.[C:30]1(=[O:40])[C@@H:38]2[C@@H:33]([CH2:34][CH2:35][CH2:36][CH2:37]2)[C:32](=O)[O:31]1>>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:29]=[C:32]([C@H:33]4[CH2:34][CH2:35][CH2:36][CH2:37][C@H:38]4[C:30]([OH:40])=[O:31])[N:15]([CH2:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][C:24]([F:25])([F:26])[F:27])=[CH:19][C:18]=4[CH3:28])[C:13]=3[CH:14]=2)=[N:3]1

Participants

3

Reactant 2

HCID 641660Hexahydrophthalic anhydride, cis-HCID 904101555-((1-Methyl-1H-pyrazol-3-yl)methoxy)-N1-(2-methyl-4-(trifluoromethoxy)benzyl)benzene-1,2-diamine

Product 1

HCID 86267446racemic cis-2-{6-[(1-Methyl-1H-pyrazol-3-yl)methoxy]-1-[2-methyl-4-(trifluoromethoxy)benzyl]-1H-benzimidazol-2-yl}cyclohexanecarboxylic acid

Procedure

The title compound was prepared using analogous conditions described in Example 92 using 5-((1-methyl-1H-pyrazol-3-yl)methoxy)-N1-(2-methyl-4-(trifluoromethoxy)benzyl)benzene-1,2-diamine and cis-hexahydroisobenzofuran-1,3-dione in Step D. MS (ESI): mass calcd. for C28H29F3N4O4, 542.20; m/z found, 543.2 [M+H]+. 1H NMR (300 MHz, DMSO-d6) δ 7.71 (d, J=7.7, 1H), 7.58 (d, J=2.2, 1H), 7.35 (s, 1H), 7.24 (s, 1H), 7.15 (s, 1H), 7.01 (d, J=10.0, 1H), 6.42 (d, J=8.8, 1H), 6.18 (d, J=2.2, 1H), 5.72-5.60 (m, 2H), 4.96 (s, 2H), 3.76 (s, 3H), 3.65 (s, 1H), 2.72 (s, 1H), 2.51 (s, 3H), 2.22-1.66 (m, 5H), 1.62-1.33 (m, 3H).

Sources & evidence

ORD record
ord-312ae8fbbb5a4ced8ddb0f5f5edc7593
Source dataset
uspto-grants-2015_02
Patent number
US08952177B2

Reaction notes

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