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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1848732Generated: October 30, 2026

Hexahydrophthalic anhydride, cis- → racemic cis-2-{6-[(5-Methylpyridin-2-yl)methoxy]-1-[2-methyl-4-(trifluoromethoxy)benzyl]-1H-benzimidazol-2-yl}cyclohexanecarboxylic acid

https://huagongshe.com/reaction/1848732

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHexahydrophthalic anhydride, cis-HCID 641660—
Reactant2-((3-Fluoro-4-nitrophenoxy)methyl)-5-methylpyridineHCID 90411084—
ReactantN1-(2-methyl-4-(trifluoromethoxy)benzyl)-5-((5-methylpyridin-2-yl)methoxy)benzene-1,2-diamineHCID 131732438—
Productracemic cis-2-{6-[(5-Methylpyridin-2-yl)methoxy]-1-[2-methyl-4-(trifluoromethoxy)benzyl]-1H-benzimidazol-2-yl}cyclohexanecarboxylic acidHCID 86267447—

Reaction Steps

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).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08952177B2
Source datasetuspto-grants-2015_02
ORD IDord-1902f677b4d248439a6627ac6e8951f4
Source noteuspto-grants-2015_02