6-(Bromomethyl)pyridine-3-carbonitrile → 1-(5-Cyano-pyridin-2-ylmethyl)-5-(3-difluoromethyl-phenyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

HRID 512519Notes

Reaction equation

HRID 512519 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1.[CH3:11][S:12]([C:15]1[CH:41]=[CH:40][C:18]([CH2:19][NH:20][C:21]([C:23]2[C:28](=[O:29])[C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH:36]([F:38])[F:37])[CH:31]=3)=[C:26]([CH3:39])[NH:25][CH:24]=2)=[O:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13]>>[CH3:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([CH2:19][NH:20][C:21]([C:23]2[C:28](=[O:29])[C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH:36]([F:37])[F:38])[CH:31]=3)=[C:26]([CH3:39])[N:25]([CH2:2][C:3]3[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=3)[CH:24]=2)=[O:22])=[CH:40][CH:41]=1)(=[O:14])=[O:13]

Participants

3

Reactant 2

HCID 219277766-(Bromomethyl)pyridine-3-carbonitrileHCID 867115675-(3-Difluoromethyl-phenyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

Product 1

HCID 867115681-(5-Cyano-pyridin-2-ylmethyl)-5-(3-difluoromethyl-phenyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide

Procedure

Example 40 is prepared as described for example 2.1, substituting benzyl bromide with 6-bromomethyl-nicotinonitrile and substituting preparation 5 with preparation 39a. ESI mass spectrum: [M+H]+=563; Retention time HPLC: 0.99 min (Z018_S04).

Workup

  1. customExample 40 is prepared
  2. custompreparation 5
  3. custom0.99 min (Z018_S04)

Sources & evidence

ORD record
ord-72bbe8dfcf944a0cbc2e31e692c0fc87
Source dataset
uspto-grants-2015_08
Patent number
US09102624B2

Reaction notes

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