3,4,5-Trifluorobenzoic acid → HCID 60197802, compound

HRID 878099Notes

Reaction equation

HRID 878099 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15].[F:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([F:27])[C:25]=1[F:26])[C:20]([OH:22])=O>>[F:27][C:24]1[CH:23]=[C:19]([CH:18]=[C:17]([F:16])[C:25]=1[F:26])[C:20]([N:2]([CH3:1])[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])=[O:22]

Participants

3

Reactant 2

HCID 8531543,4,5-Trifluorobenzoic acidHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

Product 1

HCID 60197802HCID 60197802, compound

Procedure

The title compound was prepared in analogy to example 90, from N-methyl-4-o-tolylpyridin-3-amine (example 1, intermediate a) and 3,4,5-trifluorobenzoic acid (CAS RN 121602-93-5) 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 50:50). The product-containing fractions were pooled and evaporated. The resulting brown solid was chromatographed a second time by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 50:50). Light brown solid (22%). MS (ESI): m/z=357.12 [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 50:50)
  3. customevaporated
  4. customThe resulting brown solid was chromatographed a second time by silica gel chromatography on a 10 g column
  5. washeluting with a gradient of n-heptane:EtOAc (100:0 to 50:50)

Sources & evidence

ORD record
ord-bfd73bf810d64270bacca431b6796a05
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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