Triethylamine → HCID 86636463, compound

HRID 1471594Notes

Reaction equation

HRID 1471594 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-4c6a36388bee4b39b73532f06bb56e1a
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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