3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid → HCID 86670811, compound

HRID 878289Notes

Reaction equation

HRID 878289 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH3:9])=[C:4]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[CH3:17])[CH:3]=1.[CH3:18][S:19]([C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:25]([OH:27])=O)(=[O:21])=[O:20]>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:9])[C:25](=[O:27])[C:24]2[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=[C:22]([S:19]([CH3:18])(=[O:20])=[O:21])[CH:23]=2)=[C:4]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[CH3:17])[CH:3]=1

Participants

3

Reactant 2

HCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acidHCID 577104506-chloro-4-(5-fluoro-2-methylphenyl)-N-methylpyridin-3-amine

Product 1

HCID 86670811HCID 86670811, compound

Procedure

The title compound was prepared in analogy to example 90, from [6-chloro-4-(5-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 64 hours. The compound was purified by silica gel chromatography on a 20 g column using an MPLC (ISCO) system eluting with a gradient of n-heptane:EtOAc (100:0 to 20:80). The product was further purified by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.1% formic acid) (20:80 to 98:2). Colorless foam (5%). MS (ESI): m/z=501.07 [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 20:80)
  3. customThe product was further purified by preparative HPLC (Gemini NX column)

Sources & evidence

ORD record
ord-e51a3e081d4b49ba93cb99baede9495a
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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