3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid → HCID 70663217, compound

HRID 878336Notes

Reaction equation

HRID 878336 reaction equation
[F:1][C:2]1[C:3]([CH3:16])=[C:4]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH:14][CH3:15])[CH:5]=[CH:6][CH:7]=1.[CH3:17][S:18]([C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[C:24]([OH:26])=O)(=[O:20])=[O:19]>>[F:1][C:2]1[C:3]([CH3:16])=[C:4]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH3:15])[C:24](=[O:26])[C:23]2[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=[C:21]([S:18]([CH3:17])(=[O:19])=[O:20])[CH:22]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acidHCID 70663334HCID 70663334, compound

Product 1

HCID 70663217HCID 70663217, compound

Procedure

The title compound was prepared in analogy to example 90, from [4-(3-fluoro-2-methyl-phenyl)-pyridin-3-yl]-methyl-amine and 3-(methylsulfonyl)-5-(trifluoromethyl)benzoic acid (example 114, intermediate a) after a reaction time of 23 hours at room temperature. The compound was purified by silica gel chromatography on a 20 g column using an MPLC (Flashmaster) system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). The Product was purified by preparative HPLC (Gemini NX column) with a gradient of MeOH:water (containing 0.05% formic acid) (80:20 to 98:2). Colorless solid (42%). MS (ESI): m/z=467.104 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 20 g column
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)
  3. customThe Product was purified by preparative HPLC (Gemini NX column) with a gradient of MeOH

Sources & evidence

ORD record
ord-308b6161459f4f61ba9939bda7ca4b54
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…