HCID 21075864, compound → HCID 21075853, compound

HRID 1374160Notes

Reaction equation

HRID 1374160 reaction equation
[Cl:1][C:2]1[C:3]([C:21]#[N:22])=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=2[C:15]2[N:16]=[N:17][N:18]([CH3:20])[N:19]=2)[CH:7]=1>[NH4+].CO.[Ni]>[Cl:1][C:2]1[C:3]([CH2:21][NH2:22])=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=2[C:15]2[N:16]=[N:17][N:18]([CH3:20])[N:19]=2)[CH:7]=1

Participants

5

Reactant 1

HCID 21075864HCID 21075864, compound

Product 1

HCID 21075853HCID 21075853, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 223AmmoniumSolventHCID 887MethanolSolvent

Procedure

To a solution of 3-chloro-5-[3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]-pyridine-2-carbonitrile (0.500 g, 1.59 mmol) in ammonium in methanol (40 mL 2.0 M) was added Raney 2800 nickel (slurry in water). The reaction mixture was stirred under H2 atmosphere for 3 hours, filtered through glass filter paper and concentrated under vacuum. The residue was azeotroped three times with toluene to yield crude 1-{3-chloro-5-[3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]pyridin-2-yl}methanamine that gave a mass ion (ES+) of 319.18 for M+H+.

Workup

  1. filtrationfiltered through glass
  2. filtrationfilter paper
  3. concentrationconcentrated under vacuum
  4. customThe residue was azeotroped three times with toluene

Sources & evidence

ORD record
ord-0256770ad27b4fff829e4543d32db34f
Source dataset
uspto-grants-2007_01
Patent number
US07163951B2

Reaction notes

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