3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid → HCID 70663367, compound

HRID 878305Notes

Reaction equation

HRID 878305 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[NH:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][S:25]([C:28]1[CH:29]=[C:30]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[C:31]([OH:33])=O)(=[O:27])=[O:26]>>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N:22]([CH3:23])[C:31](=[O:33])[C:30]1[CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=[C:28]([S:25]([CH3:24])(=[O:26])=[O:27])[CH:29]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acidHCID 70663307HCID 70663307, compound

Product 1

HCID 70663367HCID 70663367, compound

Procedure

The title compound was prepared in analogy to example 90, from 4-(2-(benzyloxy)-4-fluorophenyl)-N-methylpyridin-3-amine and 3-(methylsulfonyl)-5-(trifluoromethyl)benzoic acid (example 114, intermediate a) after a reaction time of 18 hours at room temperature. The compound was purified by silica gel chromatography on a 50 g column using an MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Light brown foam (637 mg, 69%). MS (ESI): m/z=559.131 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-5dd5e7a6bc934b1e8d25cc8540f02cdc
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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