Acetic Acid → 4-{[(3-ethoxy-4-methoxyphenyl)-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}benzamidine acetate

HRID 1698641Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[N:36]=C(C)O[N:33]=3)=[CH:28][CH:27]=2)[C:13]2[NH:14][C:15](=[O:24])[N:16]([C:18]3[N:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].O.[C:39]([OH:42])(=[O:41])[CH3:40]>CO.[Fe]>[C:39]([OH:42])(=[O:41])[CH3:40].[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([C:32]([NH2:36])=[NH:33])=[CH:30][CH:31]=2)[C:13]2[NH:14][C:15](=[O:24])[N:16]([C:18]3[N:19]=[CH:20][CH:21]=[CH:22][N:23]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 70 mg of 5-{(3-ethoxy-4-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 3 ml of a methanol:water:acetic acid=1:1:1 mixed solvent there was added 70 mg of iron powder, and the mixture was stirred at 60° C. for 14 hours 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 41 mg of the title compound.

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-f1dd13a94ff342debf075aa923142c08
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163787B2

Reaction notes

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