3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid → HCID 70663208, compound

HRID 878334Notes

Reaction equation

HRID 878334 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH:14][CH2:15][C:16]1[O:17][CH:18]=[CH:19][N:20]=1.[CH3:21][S:22]([C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[C:28](O)=[O:29])(=[O:24])=[O:23]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N:14]([CH2:15][C:16]1[O:17][CH:18]=[CH:19][N:20]=1)[C:28](=[O:29])[C:27]1[CH:31]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:33]=[C:25]([S:22]([CH3:21])(=[O:24])=[O:23])[CH:26]=1

Participants

3

Reactant 2

HCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acidHCID 70663682HCID 70663682, compound

Product 1

HCID 70663208HCID 70663208, compound

Procedure

The title compound was prepared in analogy to example 90, from [4-(2-chloro-phenyl)-pyridin-3-yl]-oxazol-2-ylmethyl-amine and 3-(methylsulfonyl)-5-(trifluoromethyl)benzoic acid (example 114, intermediate a) after a reaction time of 21 hours at room temperature. The compound was purified by silica gel chromatography on a 20 g column using an MPLC system (CombiFlash Companion, Isco Inc.) 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 (157 mg, 42%). MS (ESI): m/z=536.065 [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-27a6af4e45f04653945f90ffcfc6af26
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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