3-Fluoro-N-[4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-benzamide → 3-Cyclopropyl-N-[4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-5-methanesulfonyl-N-methyl-benzamide

HRID 878297Notes

Reaction equation

HRID 878297 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([CH:10]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:12]=2)[C:7]([OH:9])=O)[CH2:3][CH2:2]1.FC1C=C(C=C(C(F)(F)F)C=1)[C:21]([N:23]([C:25]1[CH:26]=[N:27][CH:28]=[CH:29][C:30]=1[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[O:38][CH3:39])C)=O>>[CH:1]1([C:4]2[CH:5]=[C:6]([CH:10]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:12]=2)[C:7]([N:23]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][C:30]=2[C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=2[O:38][CH3:39])[CH3:21])=[O:9])[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 706632783-Fluoro-N-[4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-benzamideHCID 706633783-Cyclopropyl-5-methanesulfonyl-benzoic acid

Product 1

HCID 706632043-Cyclopropyl-N-[4-(4-fluoro-2-methoxy-phenyl)-pyridin-3-yl]-5-methanesulfonyl-N-methyl-benzamide

Procedure

The title compound was prepared in analogy to example 90, from 3-cyclopropyl-5-methanesulfonyl-benzoic acid (119 mg, 495 μmol) and 4-(4-fluoro-2-methoxyphenyl)-N-methylpyridin-3-amine (example 129, intermediate) after a reaction time of 19.5 hours. The compound was purified by preparative HPLC (Gemini NX column) using a gradient of MeOH:water (containing 0.1% formic acid) (20:80 to 98:2). Off-white solid (0.082 g; 36%). MS (ESI): m/z=455.14 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-7650748eeac14874b9f7a3ebefadecaf
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…