4-Cyano-3-fluorobenzyl bromide → 1-(4-Cyano-3-fluoro-benzyl)-5-(3-difluoromethyl-phenyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

HRID 512518Notes

Reaction equation

HRID 512518 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([F:11])[CH:4]=1.[CH3:12][S:13]([C:16]1[CH:42]=[CH:41][C:19]([CH2:20][NH:21][C:22]([C:24]2[C:29](=[O:30])[C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]([F:39])[F:38])[CH:32]=3)=[C:27]([CH3:40])[NH:26][CH:25]=2)=[O:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>>[CH3:12][S:13]([C:16]1[CH:17]=[CH:18][C:19]([CH2:20][NH:21][C:22]([C:24]2[C:29](=[O:30])[C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]([F:38])[F:39])[CH:32]=3)=[C:27]([CH3:40])[N:26]([CH2:2][C:3]3[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([F:11])[CH:4]=3)[CH:25]=2)=[O:23])=[CH:41][CH:42]=1)(=[O:15])=[O:14]

Participants

3

Reactant 2

HCID 27784664-Cyano-3-fluorobenzyl bromideHCID 867115675-(3-Difluoromethyl-phenyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

Product 1

HCID 867115661-(4-Cyano-3-fluoro-benzyl)-5-(3-difluoromethyl-phenyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

Procedure

Example 39 is prepared as described for example 2.1, substituting benzyl bromide with 4-bromomethyl-2-fluoro-benzonitrile and substituting preparation 5 with preparation 39a. ESI mass spectrum: [M+H]+=580; Retention time HPLC: 1.03 min (Z018_S04).

Workup

  1. customExample 39 is prepared
  2. custompreparation 5
  3. custom1.03 min (Z018_S04)

Sources & evidence

ORD record
ord-98ecf8759aba4b73960a6037dea6739e
Source dataset
uspto-grants-2015_08
Patent number
US09102624B2

Reaction notes

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