Triethylamine → HCID 57969191, compound

HRID 1483726Notes

Reaction equation

HRID 1483726 reaction equation
Cl[C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].Cl[C:13]1[C:18]([C:19](N)=O)=[CH:17][N:16]=[C:15](Cl)[CH:14]=1.[CH2:23](N(CC)CC)C>C(#N)C>[CH2:17]([NH:16][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5])[C:18]1[CH:13]=[CH:14][CH:15]=[CH:23][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6000444,6-DichloronicotinamideHCID 221427782,6-Dichloropyridine-3-carboxamide

Product 1

HCID 57969191HCID 57969191, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2,6-dichloro-nicotinamide (1) (2.3 g, 12.2 mmol) in acetonitrile (anhydrous, 100 mL) were added 2-benzylamine (2) (1.3 g, 12.2 mmol) and triethylamine (1.7 mL, 12.2 mmol). The reaction was heated at 60° C. for 4 hours. The solution was cooled to room temperature and filtered. The filtrate was evaporated in vacuo. Purification was achieved by Biotage silica gel chromatography with 5%-50% EtOAc/hexanes gradient to afford 1.71 g (54% yield) of the title compound.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated in vacuo
  4. customPurification

Sources & evidence

ORD record
ord-de63907a0faf4581a253812fd6744c72
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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