3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid → HCID 70663318, compound

HRID 878295Notes

Reaction equation

HRID 878295 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[NH:21][CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][S:24]([C:27]1[CH:28]=[C:29]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[C:30]([OH:32])=O)(=[O:26])=[O:25]>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[N:21]([CH3:22])[C:30](=[O:32])[C:29]1[CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=[C:27]([S:24]([CH3:23])(=[O:25])=[O:26])[CH:28]=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 70663350HCID 70663350, compound

Product 1

HCID 70663318HCID 70663318, compound

Procedure

The title compound was prepared in analogy to example 90, from 4-(2-(benzyloxy)phenyl)-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 yellow foam (83%). MS (ESI): m/z=541.140 [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-42d9294f7e2f41baae4c952056a9eed1
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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