Ethylamine → N-(2-Bromo-6-methoxy-4-methyl-3-pyridinyl)-2-ethylamino-3-pyridinecarboxamide

HRID 2380246Notes

Reaction equation

HRID 2380246 reaction equation
[Br:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[C:12](Cl)=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[C:6]([CH3:18])[CH:5]=[C:4]([O:19][CH3:20])[N:3]=1.O1CCOCC1.[CH2:27]([NH2:29])[CH3:28]>C(OCC)(=O)C>[Br:1][C:2]1[C:7]([NH:8][C:9]([C:11]2[C:12]([NH:29][CH2:27][CH3:28])=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[C:6]([CH3:18])[CH:5]=[C:4]([O:19][CH3:20])[N:3]=1

Participants

5

Reactant 3

HCID 6341EthylamineHCID 312751,4-DioxaneHCID 19960021N-(2-bromo-6-methoxy-4-methyl-3-pyridinyl)-2-chloro-3-pyridinecarboxamide

Product 1

HCID 19960032N-(2-Bromo-6-methoxy-4-methyl-3-pyridinyl)-2-ethylamino-3-pyridinecarboxamideYield 44.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of N-(2-bromo-6-methoxy-4-methyl-3-pyridinyl)-2-chloro-3-pyridinecarboxamide (2.1 g), dioxane (10 ml), and ethylamine (0.5 g) was heated to 140° C. in a sealed tube for 5 hours. The cooled mixture was diluted with ethyl acetate, washed with water, and the organic phase was dried (anhydrous magnesium sulfate) and concentrated. The product was purified on a silica gel column (methylene chloride/ethyl acetate, 99:1) and crystallized by trituration with diisopropyl ether to give 0.95 g of the title compound.

Workup

  1. washwashed with water
  2. dry with materialthe organic phase was dried (anhydrous magnesium sulfate)
  3. concentrationconcentrated
  4. customThe product was purified on a silica gel column (methylene chloride/ethyl acetate, 99:1)
  5. customcrystallized by trituration with diisopropyl ether

Sources & evidence

ORD record
ord-b78d061dc707459e9140f7cae25b93d4
Source dataset
uspto-grants-1994_11
Patent number
US05366972

Reaction notes

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