3-Methanesulfonyl-5-(trifluoromethyl)benzoic acid → N-[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-oxazol-2-ylmethyl-5-trifluoromethyl-benzamide

HRID 877990Notes

Reaction equation

HRID 877990 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[NH:14][CH2:15][C:16]2[O:17][CH:18]=[CH:19][N:20]=2)=[C:4]([O:21][CH3:22])[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](O)=[O:31])(=[O:26])=[O:25]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH2:15][C:16]2[O:17][CH:18]=[CH:19][N:20]=2)[C:30](=[O:31])[C:29]2[CH:33]=[C:34]([C:36]([F:39])([F:37])[F:38])[CH:35]=[C:27]([S:24]([CH3:23])(=[O:26])=[O:25])[CH:28]=2)=[C:4]([O:21][CH3:22])[CH:3]=1

Participants

3

Reactant 2

HCID 215445163-Methanesulfonyl-5-(trifluoromethyl)benzoic acidHCID 70663572[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-yl]-oxazol-2-ylmethyl-amine

Product 1

HCID 60197193N-[4-(4-Fluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-oxazol-2-ylmethyl-5-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 90, from [4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-oxazol-2-ylmethyl-amine and 3-methanesulfonyl-5-trifluoromethyl-benzoic acid (example 144, intermediate a) after a reaction time of 72 hours. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). The product-containing fractions were pooled and evaporated. The remaining red solid was purified by preparative HPLC (Gemini NX) with a gradient of methanol:water containing 0.05% formic acid (80:20 to 98:2). Colorless foam (41%). MS (ESI): m/z=550.105 [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. customevaporated
  4. customThe remaining red solid was purified by preparative HPLC (Gemini NX) with a gradient of methanol

Sources & evidence

ORD record
ord-4314393ade2647619261da477fc10ad3
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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