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

HRID 1161360Notes

Reaction equation

HRID 1161360 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:14](O)=[O:15])[C:11]3[CH:23]=[C:24]([F:28])[C:25]([F:27])=[CH:26][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[NH2:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][C:31]=1[C:38]([F:41])([F:40])[F:39]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:14]([NH:29][C:30]3[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][C:31]=3[C:38]([F:39])([F:40])[F:41])=[O:15])[C:11]3[CH:23]=[C:24]([F:28])[C:25]([F:27])=[CH:26][C:10]=3[N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27794884-Amino-3-(trifluoromethyl)benzonitrileHCID 66619321[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acid

Product 1

HCID 866320262-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-N-(4-cyano-2-trifluoromethyl-phenyl)-2-cyclohexyl-acetamide

Procedure

The title compound was prepared in analogy to example 22, int. d) from [2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acid and 4-amino-3-trifluoromethylbenzonitrile. The compound was purified by using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane to n-heptane/ethyl acetate (1:0 to 4:1 v/v) and subsequent purification by preparative HPLC using a Gemini column and a gradient of acetonitrile:water (containing 0.5% formic acid). Colorless foam (47%). MS (ES+): M+H: 573.2.

Workup

  1. customThe compound was purified
  2. washeluting with a gradient of heptane to n-heptane/ethyl acetate (1:0 to 4:1 v/v) and subsequent purification by preparative HPLC

Sources & evidence

ORD record
ord-57dd2870e1eb4dc2950d74fde07c036e
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

Loading…