Triethylamine → HCID 86636463, compound

HRID 1255737Notes

Reaction equation

HRID 1255737 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].ClC1C=[CH:20][C:16]([C:17](N)=O)=[C:15](OC(C)C)N=1.C([N:28](CC)CC)C>C(#N)C>[C:16]([NH:28][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5])([CH3:20])([CH3:17])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 221427782,6-Dichloropyridine-3-carboxamideHCID 57968821HCID 57968821, compound

Product 1

HCID 86636463HCID 86636463, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,6-dichloro-nicotinamide (1) (4 g, 20.9 mmol) in acetonitrile (anhydrous, 60 mL) were added tert-butylamine (2) (13.28 mL, 12.6 mmol) and triethylamine (15.7 mL, 12.6 mmol). The reaction was heated at 80° C. for 2 days. The solution was cooled to room temperature and the resulting suspension was filtered. The filtrate was concentrated in vacuo. The residue was purified by Biotage silica gel chromatography with 20%-100% EtOAc/hexanes gradient elution to afford 850 mg (18% yield) of the title compound.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationthe resulting suspension was filtered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by Biotage silica gel chromatography with 20%-100% EtOAc/hexanes gradient elution

Sources & evidence

ORD record
ord-d2396c5403a44769a47e114c08221662
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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