N-[4-(2-Fluoro-6-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide → 3-Methanesulfonyl-N-(2,2,2-trifluoro-ethyl)-N-[4-(2-trifluoromethoxy-phenyl)-pyridin-3-yl]-5-trifluoromethyl-benzamide

HRID 878340Notes

Reaction equation

HRID 878340 reaction equation
[F:1][C:2]([F:23])([F:22])[CH2:3][NH:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][C:18]([F:21])([F:20])[F:19].FC1C=CC=C(OC)C=1C1C=CN=CC=1N(CC(F)(F)F)[C:40](=[O:55])[C:41]1[CH:46]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:44]=[C:43]([S:51]([CH3:54])(=[O:53])=[O:52])[CH:42]=1>>[CH3:54][S:51]([C:43]1[CH:42]=[C:41]([CH:46]=[C:45]([C:47]([F:48])([F:49])[F:50])[CH:44]=1)[C:40]([N:4]([CH2:3][C:2]([F:1])([F:22])[F:23])[C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][C:18]([F:19])([F:20])[F:21])=[O:55])(=[O:53])=[O:52]

Participants

3

Reactant 2

HCID 86670807N-[4-(2-Fluoro-6-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide2×HCID 86670817(2,2,2-Trifluoro-ethyl)-[4-(2-trifluoromethoxy-phenyl)-pyridin-3-yl]-amine

Product 1

HCID 866708163-Methanesulfonyl-N-(2,2,2-trifluoro-ethyl)-N-[4-(2-trifluoromethoxy-phenyl)-pyridin-3-yl]-5-trifluoromethyl-benzamideYield 20%

Procedure

The title compound was prepared in analogy to example 72, intermediate, from (2,2,2-trifluoro-ethyl)-[4-(2-trifluoromethoxy-phenyl)-pyridin-3-yl]-amine (37) and 3-methanesulfonyl-5-trifluoromethyl-benzoyl chloride (example 223, intermediate d) after a reaction time of 12 hours at 25° C. The crude product was purified by preparative HPLC (ammonium acetate/acetonitrile) to give the desired compound as an off-white solid (12 mg, 20%). MS (ESI): m/z=587.2 [M+H]+.

Workup

  1. customThe crude product was purified by preparative HPLC (ammonium acetate/acetonitrile)

Sources & evidence

ORD record
ord-64532416ac55476c90ad1c5c3e16326f
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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