Triethylamine → N-(6-methoxypyridin-3-yl)pivalamide

HRID 906382Notes

Reaction equation

HRID 906382 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.CCN(CC)CC.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 811216-Methoxy-3-pyridinylamine

Product 1

HCID 5323848N-(6-methoxypyridin-3-yl)pivalamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 6-methoxy-pyridin-3-amine (Aldrich, 10.0 g, 77 mmol) in anhydrous CH2Cl2 (100 ml) at 0° C. was added Et3N (13.9 ml, 100.1 mmol) and a solution of pivaloyl chloride (10.5 ml, 84.7 mmol) in CH2Cl2 (20 ml). The mixture was stirred at 0° C. for 10 min and at room temperature for 2 h. After quenched with ice, the reaction was diluted with CH2Cl2, washed with 1M NaOH, brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes) to yield the title compound as orange solid.

Workup

  1. customAfter quenched with ice
  2. additionthe reaction was diluted with CH2Cl2
  3. washwashed with 1M NaOH, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-482bd6619dd64bad9d6c746f5cf03369
Source dataset
uspto-grants-2011_09
Patent number
US08012992B2

Reaction notes

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