2-Amino-3-cyanopyridine → HCID 20310509, compound

HRID 1763480Notes

Reaction equation

HRID 1763480 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:10]([N:17]1[C:21]([C:22](Cl)=[O:23])=[N:20][N:19]=[N:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1>[CH2:10]([N:17]1[C:21]([C:22]([NH:1][C:2]2[C:3]([C:4]#[N:5])=[CH:6][CH:7]=[CH:8][N:9]=2)=[O:23])=[N:20][N:19]=[N:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 8182592-Amino-3-cyanopyridineHCID 204638761-benzyl-1H-tetrazole-5-carbonyl chloride

Product 1

HCID 20310509HCID 20310509, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Aminonicotinonitrile is reacted with 1-benzyl-1H-tetrazole-5-carbonyl chloride in stoichiometric amounts in the presence of an acid acceptor (pyridine). The product is washed with water, brine, and dried over CaCl2 to yield 1-benzyl-N-(3-cyano-2-pyridyl)-1H-tetrazole-5-carboxamide. The benzyl protecting group is then removed by hydrogenolysis with 10% Pd/C. The product is stirred in water and N NaOH is added to produce the title compound upon lyophilization.

Workup

  1. washThe product is washed with water, brine
  2. dry with materialdried over CaCl2

Sources & evidence

ORD record
ord-4c94ebbf074242d28b0609616e85370c
Source dataset
uspto-grants-1978_09
Patent number
US04112101

Reaction notes

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