3-Chloro-5-methanesulfonylbenzoic acid → 3-Chloro-N-[4-(4-fluoro-2-methoxy-phenyl)-6-methyl-pyridin-3-yl]-5-methanesulfonyl-N-methyl-benzamide

HRID 878348Notes

Reaction equation

HRID 878348 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][CH3:16])=[C:4]([O:17][CH3:18])[CH:3]=1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:28]=1)[C:23]([OH:25])=O>>[Cl:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:28]=1)[C:23]([N:15]([C:9]1[CH:10]=[N:11][C:12]([CH3:14])=[CH:13][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[O:17][CH3:18])[CH3:16])=[O:25]

Participants

3

Reactant 2

HCID 189525313-Chloro-5-methanesulfonylbenzoic acidHCID 706636684-(4-fluoro-2-methoxyphenyl)-N,6-dimethylpyridin-3-amine

Product 1

HCID 706632383-Chloro-N-[4-(4-fluoro-2-methoxy-phenyl)-6-methyl-pyridin-3-yl]-5-methanesulfonyl-N-methyl-benzamide

Procedure

The title compound was prepared in analogy to example 90, from 4-(4-fluoro-2-methoxyphenyl)-N,6-dimethylpyridin-3-amine and 3-chloro-5-(methylsulfonyl)benzoic acid (example 114, intermediate a) after a reaction time of 15.5 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 oil (41%). MS (ESI): m/z=463.09 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-77f075b10325410781b7bca48f563214
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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