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

HRID 53525Notes

Reaction equation

[CH2:1]([NH2:3])[CH3:2].[Br:4][C:5]1[C:10]([N:11]([CH3:21])[C:12]([C:14]2[C:15](Cl)=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:9][CH:8]=[C:7]([O:22][CH3:23])[N:6]=1>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[Br:4][C:5]1[C:10]([N:11]([CH3:21])[C:12]([C:14]2[C:15]([NH:3][CH2:1][CH3:2])=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:9][CH:8]=[C:7]([O:22][CH3:23])[N:6]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Ethylamine (0.7 g) was added to a solution of N-(2-bromo-6-methoxy-3-pyridinyl)-2-chloro-N-methyl-3-pyridinecarboxamide (1.9 g) in xylene (5 ml), and the resulting mixture was sealed in a pressure bottle and heated at 150° C. for 4 hours. The solution was diluted with ethyl acetate, washed with water, dried (anhydrous magnesium sulfate), concentrated, and purified on a silica gel column (ethyl acetate/hexane, 1:4) to give 1.5 g of the title compound, suitable for use in the next reaction.

Workup

customthe resulting mixture was sealed in a pressure bottle
washwashed with water
dry with materialdried (anhydrous magnesium sulfate)
concentrationconcentrated
custompurified on a silica gel column (ethyl acetate/hexane, 1:4)

Sources & evidence

ORD record: ord-fae9aa912372442baf3cb2ca30d2909b
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05620974

Reaction notes

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