6-(Bromomethyl)pyridine-3-carbonitrile → 1-(5-Cyano-pyridin-2-ylmethyl)-2-methyl-4-oxo-2'-trifluoromethyl-1,4-dihydro-[3,4']bipyridinyl-5-carboxylic acid methylamide

HRID 512522Notes

Reaction equation

HRID 512522 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][NH:12][C:13]([C:15]1[C:16](=[O:32])[C:17]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)=[C:18]([CH3:21])[NH:19][CH:20]=1)=[O:14]>>[CH3:11][NH:12][C:13]([C:15]1[C:16](=[O:32])[C:17]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)=[C:18]([CH3:21])[N:19]([CH2:2][C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=2)[CH:20]=1)=[O:14]

Participants

3

Reactant 2

HCID 219277766-(Bromomethyl)pyridine-3-carbonitrileHCID 867115712-Methyl-4-oxo-2'-trifluoromethyl-1,4-dihydro-[3,4']bipyridinyl-5-carboxylic acid methylamide

Product 1

HCID 867115731-(5-Cyano-pyridin-2-ylmethyl)-2-methyl-4-oxo-2'-trifluoromethyl-1,4-dihydro-[3,4']bipyridinyl-5-carboxylic acid methylamide

Procedure

Example 44 is prepared as described for example 2.1, substituting benzyl bromide with 6-bromomethyl-nicotinonitrile and substituting preparation 5 with preparation 36a. ESI mass spectrum: [M+H]+=428; Retention time HPLC: 0.99 min (Z018_S04).

Workup

  1. customExample 44 is prepared
  2. custompreparation 5
  3. custom0.99 min (Z018_S04)

Sources & evidence

ORD record
ord-62c6710df9b24fa790a0c51677cecd73
Source dataset
uspto-grants-2015_08
Patent number
US09102624B2

Reaction notes

Loading…