4-(4-fluoro-2-methoxyphenyl)-6-methyl-N-(2,2,2-trifluoroethyl)pyridin-3-amine → N-[4-(4-Fluoro-2-methoxy-phenyl)-6-methyl-pyridin-3-yl]-3-methanesulfonyl-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide

HRID 878356Notes

Reaction equation

HRID 878356 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10][C:9]=2[NH:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[C:4]([O:21][CH3:22])[CH:3]=1.FC1C=CC=C(OC)C=1C1C=CN=CC=1N(CC(F)(F)F)[C:39](=[O:54])[C:40]1[CH:45]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:43]=[C:42]([S:50]([CH3:53])(=[O:52])=[O:51])[CH:41]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10][C:9]=2[N:15]([CH2:16][C:17]([F:19])([F:18])[F:20])[C:39](=[O:54])[C:40]2[CH:45]=[C:44]([C:46]([F:49])([F:47])[F:48])[CH:43]=[C:42]([S:50]([CH3:53])(=[O:52])=[O:51])[CH:41]=2)=[C:4]([O:21][CH3:22])[CH:3]=1

Participants

3

Reactant 2

HCID 706635044-(4-fluoro-2-methoxyphenyl)-6-methyl-N-(2,2,2-trifluoroethyl)pyridin-3-amineHCID 86670807N-[4-(2-Fluoro-6-methoxy-phenyl)-pyridin-3-yl]-3-methanesulfonyl-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide2×

Product 1

HCID 86670820N-[4-(4-Fluoro-2-methoxy-phenyl)-6-methyl-pyridin-3-yl]-3-methanesulfonyl-N-(2,2,2-trifluoro-ethyl)-5-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 72, intermediate, from 4-(4-fluoro-2-methoxyphenyl)-6-methyl-N-(2,2,2-trifluoroethyl)pyridin-3-amine and 3-(methylsulfonyl)-5-(trifluoromethyl)benzoyl chloride (example 223, intermediate d) after a reaction time of 42 hours. The product was purified by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.1% formic acid) (20:80 to 98:2). Colorless solid (32%). MS (ESI): m/z=565.10 [M+H]+.

Workup

  1. customThe product was purified by preparative HPLC (Gemini NX column)

Sources & evidence

ORD record
ord-ddbcc0a8baa94361b7a81f0aabaaf43c
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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