4-Amino-3-(trifluoromethyl)benzonitrile → N-(4-Cyano-2-trifluoromethyl-phenyl)-2-cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-acetamide

HRID 1161362Notes

Reaction equation

HRID 1161362 reaction equation
[CH:1]1([CH:7]([N:11]2[C:15]3[CH:16]=[C:17]([F:21])[C:18]([F:20])=[CH:19][C:14]=3[N:13]=[C:12]2[C:22]2[C:23]([O:30][CH3:31])=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[C:8]([OH:10])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:32][C:33]1[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][C:34]=1[C:41]([F:44])([F:43])[F:42]>>[C:37]([C:36]1[CH:39]=[CH:40][C:33]([NH:32][C:8](=[O:10])[CH:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:11]2[C:15]3[CH:16]=[C:17]([F:21])[C:18]([F:20])=[CH:19][C:14]=3[N:13]=[C:12]2[C:22]2[C:23]([O:30][CH3:31])=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)=[C:34]([C:41]([F:42])([F:43])[F:44])[CH:35]=1)#[N:38]

Participants

3

Reactant 2

HCID 27794884-Amino-3-(trifluoromethyl)benzonitrileHCID 66619285Cyclohexyl-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-acetic acid

Product 1

HCID 68645289N-(4-Cyano-2-trifluoromethyl-phenyl)-2-cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-acetamide

Procedure

The title compound was prepared in analogy to example 22, int. d) from cyclohexyl-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-acetic acid and 4-amino-3-trifluoromethylbenzonitrile. The crude product was purified on a preparative HPLC system (Phenomenex Gemini column) using a gradient of acetonitrile and water (containing 0.5% formic acid). Light brown foam (19%). MS (TS) (M+H+)+: 600.3.

Workup

  1. customThe crude product was purified on a preparative HPLC system (Phenomenex Gemini column)

Sources & evidence

ORD record
ord-526c20c5c8aa47758aca5fba5aa38393
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

Loading…