Ethanolamine → HCID 178433882, compound

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[N:32]=[C:31]([CH3:33])/[C:12](=[N:13]/[NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]([C:22]4[CH:23]=[CH:24][CH:25]=[C:26]([C:28]([OH:30])=[O:29])[CH:27]=4)[C:20]=3[OH:21])/[C:10]2=[O:11])=[CH:6][C:7]=1[CH3:8].O.[CH2:35]([CH2:37][NH2:38])[OH:36]>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[N:32]=[C:31]([CH3:33])/[C:12](=[N:13]/[NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[C:19]([C:22]4[CH:23]=[CH:24][CH:25]=[C:26]([C:28]([OH:30])=[O:29])[CH:27]=4)[C:20]=3[OH:21])/[C:10]2=[O:11])=[CH:6][C:7]=1[CH3:8].[CH2:35]([CH2:37][NH2:38])[OH:36]

Participants

Procedure

Eltrombopag crude orange solid (1 g) was stirred in 16.75 ml of THF at approximately 30° C. Water (2.0 ml) was added slowly so as to maintain a temperature greater then 28° C. When addition was complete, the temperature was returned to 30° C. and the solution filtered through a glass fiber pad (2× Whatman GFC filters) to remove particulate matter. The filter was washed through with THF (2.0 ml) which was added to the filtrate. The filtrate was allowed to cool to room temperature. Ethanolamine (0.324 g, 2.35 mol. equiv.) was dissolved in IMS (26 ml) at 22° C. and stirred under a nitrogen atmosphere at 22° C. The filtrate containing the free acid was added to the ethanolamine solution over 20 to 30 minutes. The resulting dark red suspension was stirred for 3 hours and the solid isolated by filtration and dried at 50° C. in a vacuum oven over night to yield 1.22 g (96%) of the title compound.