Acetic Acid → 4-({[2-fluoro-3-(2-fluoroethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl}amino)benzamidine acetate
Reaction equation
[F:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][F:11])=[CH:6][C:5]([O:12][CH3:13])=[CH:4][C:3]=1[CH:14]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[N:38]=C(C)O[N:35]=2)=[CH:30][CH:29]=1)[C:15]1[NH:16][C:17](=[O:26])[N:18]([C:20]2[N:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[N:19]=1.O.[C:41]([OH:44])(=[O:43])[CH3:42]>CO.[Fe]>[C:41]([OH:44])(=[O:43])[CH3:42].[F:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][F:11])=[CH:6][C:5]([O:12][CH3:13])=[CH:4][C:3]=1[CH:14]([NH:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]([NH2:38])=[NH:35])=[CH:32][CH:33]=1)[C:15]1[NH:16][C:17](=[O:26])[N:18]([C:20]2[N:21]=[CH:22][CH:23]=[CH:24][N:25]=2)[N:19]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
After adding 1.2 g of iron powder to a solution of 1.2 g of 5-{[2-fluoro-3-(2-fluoroethoxy)-5-methoxyphenyl]-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-2-pyrimidin-2-yl-2,4-dihydro-[1,2,4]triazol-3-one in 18 ml of a methanol:water:acetic acid=1:1:1 mixed solvent, the mixture was stirred at 65° C. for 24 hours and 30 minutes under a nitrogen atmosphere. After filtering the reaction mixture, it was purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give the title compound (750 mg) as a light yellow solid.
Workup
- filtrationAfter filtering the reaction mixture, it
- customwas purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid)
Sources & evidence
- ORD record
- ord-f9883d5017904cb9b2f1bcfe2d6ae496
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816522B2
Reaction notes
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