Triethylamine → HCID 57969017, compound

HRID 1255697Notes

Reaction equation

HRID 1255697 reaction equation
ClC1N=[C:9](Cl)[CH:8]=[CH:7][C:3]=1[C:4](N)=O.[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[C:15]([NH:22][CH2:23][CH2:24][O:25][CH3:26])[N:14]=1.[CH2:27](N(CC)CC)C>C(#N)C>[CH2:26]([O:25][CH2:24][CH2:23][NH:22][C:15]1[N:14]=[C:13]([Cl:12])[CH:21]=[CH:20][C:16]=1[C:17]([NH2:19])=[O:18])[C:4]1[CH:3]=[CH:7][CH:8]=[CH:9][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 221427782,6-Dichloropyridine-3-carboxamideHCID 57969164HCID 57969164, compound

Product 1

HCID 57969017HCID 57969017, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2,6-dichloro-nicotinamide (1) (12.6 g, 66.1 mmol) in acetonitrile (anhydrous, 200 mL) were added 2-benzyloxy-ethylamine (2) (10 g, 66.1 mmol) and triethylamine (11 mL, 79.3 mmol). The reaction was heated at 60° C. for 2 days. The solution was cooled to room temperature and the suspension was filtered. The filtrate was evaporated in vacuo. The residue was purified by Biotage with 25%-100% EtOAc/hexanes to afford 15.8 g (78.3% yield) of the title compound.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationthe suspension was filtered
  3. customThe filtrate was evaporated in vacuo
  4. customThe residue was purified by Biotage with 25%-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-bb395e3a3fb440338631e33222b935c3
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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