2-Amino-2-cyanoacetamide → N-(2-amino-1-cyano-2-oxoethyl)-2,6-dimethylisonicotinamide

HRID 1771136Notes

Reaction equation

HRID 1771136 reaction equation
[NH2:1][CH:2]([C:6]#[N:7])[C:3]([NH2:5])=[O:4].CC1C=C(C=C(C)N=1)CCl.[CH3:18][C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([CH3:28])[N:27]=1)[C:22](O)=[O:23]>N1C=CC=CC=1.S(Cl)(Cl)=O>[NH2:5][C:3](=[O:4])[CH:2]([NH:1][C:22](=[O:23])[C:21]1[CH:25]=[C:26]([CH3:28])[N:27]=[C:19]([CH3:18])[CH:20]=1)[C:6]#[N:7]

Participants

6

Reactant 3

HCID 983412-Amino-2-cyanoacetamideHCID 45318962,6-Dimethylpyridine-4-carboxylic acidHCID 135828144-(Chloromethyl)-2,6-dimethylpyridine

Product 1

HCID 71060853N-(2-amino-1-cyano-2-oxoethyl)-2,6-dimethylisonicotinamideYield 43.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 24386Thionyl ChlorideSolvent

Procedure

2-amino 2-cyano acetamide (1.4 g, 0.01473 mol, 1 eq) in pyridine (15 ml) is stirred for 1 h at room temperature, to this 2,6-dimethyl isonicotinyl chloride (2.5 g, 0.1473 mol, 1 eq) [prepared by stirring a mixture of 2,6-dimethyl isonicotinic acid (2.5 g, 0.0465 mol, 1 eq) in thionyl chloride (15 ml) at 85° C. for 2 hr, thionyl chloride was removed in vacuum under nitrogen] is added at 0° C. and the reaction mixture is stirred at room temperature for 14 h, after the completion of the reaction pyridine is removed under vacuum and the crude product is purified by column chromatography to afford (1.5 g) of the titled compound;

Workup

  1. customprepared
  2. customthionyl chloride was removed in vacuum under nitrogen]
  3. additionis added at 0° C.
  4. stirringthe reaction mixture is stirred at room temperature for 14 h
  5. customafter the completion of the reaction pyridine
  6. customis removed under vacuum
  7. customthe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-b9ac15e53b9c4b07994a74580fbdbec0
Source dataset
uspto-grants-2016_02
Patent number
US09249114B2

Reaction notes

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