Acetic Acid → 4-{[(8-methoxy-4H-benzo[1,3]dioxin-6-yl)-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}benzamidine acetate

HRID 1161411Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:12]2[O:11][CH2:10][O:9][CH2:8][C:7]=2[CH:6]=[C:5]([CH:13]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[N:37]=C(C)O[N:34]=3)=[CH:29][CH:28]=2)[C:14]2[NH:15][C:16](=[O:25])[N:17]([C:19]3[N:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:18]=2)[CH:4]=1.O.[C:40]([OH:43])(=[O:42])[CH3:41]>CO.[Fe]>[C:40]([OH:43])(=[O:42])[CH3:41].[CH3:1][O:2][C:3]1[C:12]2[O:11][CH2:10][O:9][CH2:8][C:7]=2[CH:6]=[C:5]([CH:13]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([NH2:37])=[NH:34])=[CH:29][CH:28]=2)[C:14]2[NH:15][C:16](=[O:25])[N:17]([C:19]3[N:20]=[CH:21][CH:22]=[CH:23][N:24]=3)[N:18]=2)[CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 814 mg of 5-{(8-methoxy-4H-benzo[1,3]dioxin-6-yl)-[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 15 ml of a methanol:water:acetic acid=1:1:1 mixed solvent there was added 1 g of iron powder, and the mixture was stirred overnight at 60° C. under a nitrogen atmosphere. After adding 7.5 ml of a methanol:water:acetic acid=1:1:1 mixed solvent to the reaction mixture, the mixture was further stirred at 60° C. for 5 hours. 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 (476 mg).

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-61536b40fc43488f8fcf771f3e8a99af
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816522B2

Reaction notes

Loading…