HCID 70663168, compound → HCID 70663354, compound

HRID 878230Notes

Reaction equation

HRID 878230 reaction equation
FC1C=C(C=C(C(F)(F)F)C=1)[C:5]([N:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[O:22][CH3:23])C)=O.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[N:41]=1)[C:36]([OH:38])=O>>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:7]([CH3:5])[C:36](=[O:38])[C:35]2[CH:39]=[C:40]([C:42]([F:45])([F:44])[F:43])[N:41]=[C:33]([O:32][CH3:31])[CH:34]=2)=[C:16]([O:22][CH3:23])[CH:17]=1

Participants

3

Reactant 2

HCID 70663168HCID 70663168, compoundHCID 70663278HCID 70663278, compound

Product 1

HCID 70663354HCID 70663354, compound

Procedure

The title compound was prepared in analogy to example 90, from [4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-methyl-amine (example 129, intermediate) and 2-methoxy-6-trifluoromethyl-isonicotinic acid after a reaction time of 64 hours. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100), followed by a second chromatography using preparative HPLC (Gemini NX column) and a gradient of methanol:water (containing 0.1% formic acid) (20:80 to 98:2) as eluant. Colorless solid (33%). MS (ESI): m/z=436.13 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 10 g column
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-3723eb7468804e1c8cedb88fbe00b8ed
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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