N-[4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl]-N-methyl-3-morpholin-4-ylsulfonyl-5-(trifluoromethyl)benzamide → N-[4-(4-Fluoro-2-methoxy-phenyl)-6-methyl-pyridin-3-yl]-N-methyl-3-(morpholine-4-sulfonyl)-5-trifluoromethyl-benzamide

HRID 878350Notes

Reaction equation

HRID 878350 reaction equation
F[C:2]1C=CC(C2C=C(C)N=CC=2NC)=C(OC)C=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][C:27]=2[N:32]([CH3:54])[C:33](=[O:53])[C:34]2[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[C:36]([S:44]([N:47]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]3)(=[O:46])=[O:45])[CH:35]=2)=[C:22]([O:55][CH3:56])[CH:21]=1>>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[C:30]([CH3:2])[N:29]=[CH:28][C:27]=2[N:32]([CH3:54])[C:33](=[O:53])[C:34]2[CH:39]=[C:38]([C:40]([F:41])([F:43])[F:42])[CH:37]=[C:36]([S:44]([N:47]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]3)(=[O:45])=[O:46])[CH:35]=2)=[C:22]([O:55][CH3:56])[CH:21]=1

Participants

3

Reactant 2

HCID 60196904N-[4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl]-N-methyl-3-morpholin-4-ylsulfonyl-5-(trifluoromethyl)benzamideHCID 706636684-(4-fluoro-2-methoxyphenyl)-N,6-dimethylpyridin-3-amine

Product 1

HCID 70663244N-[4-(4-Fluoro-2-methoxy-phenyl)-6-methyl-pyridin-3-yl]-N-methyl-3-(morpholine-4-sulfonyl)-5-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 90, from 4-(4-fluoro-2-methoxyphenyl)-N,6-dimethylpyridin-3-amine (example 301, intermediate a) and 3-(morpholinosulfonyl)-5-(trifluoromethyl)benzoic acid (example 256, intermediate) after a reaction time of 15.5 hours. The compound was purified by silica gel chromatography on a 20 g column using an MPLC system eluting with EtOAc (isocratic). 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 oil (67%). MS (ESI): m/z=568.15 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 20 g column
  2. washeluting with EtOAc (isocratic)
  3. customThe product was purified by preparative HPLC (Gemini NX column)

Sources & evidence

ORD record
ord-b5c35aeb07ab4e98b1e79fbde8b11f7a
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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