3-Fluoro-5-(trifluoromethyl)benzoyl chloride → 3-Fluoro-N-[4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide

HRID 878141Notes

Reaction equation

HRID 878141 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[C:4]([O:20][CH3:21])[CH:3]=1.[F:22][C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[C:26](Cl)=[O:27]>>[F:22][C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=1)[C:26]([N:14]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[O:20][CH3:21])[CH2:15][C:16]([F:18])([F:17])[F:19])=[O:27]

Participants

3

Reactant 2

HCID 5193643-Fluoro-5-(trifluoromethyl)benzoyl chlorideHCID 70663530[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-amine

Product 1

HCID 601979143-Fluoro-N-[4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 72, intermediate, from [4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-amine (example 133, intermediate a) and 3-fluoro-5-(trifluoromethyl)benzoic acid chloride (CAS RN 171243-30-4). The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 50:50), followed by preparative HPLC using a gradient of methanol:water (10:50 to 95:5). Colorless solid (22%). MS (ESI): m/z=491.099 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 50:50)

Sources & evidence

ORD record
ord-d7832cad6ee844d8822a8bfd0251a44e
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…