Methanol → 4-({[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-[5-oxo-1-(3-oxo-3,4-dihydropyrazin-2-yl)-4,5-dihydro-1H-[1,2,4]triazol-3-yl]methyl}amino)benzamidine acetate

HRID 1161563Notes

Reaction equation

C[OH:2].O.[Si]([O:11][CH2:12][CH2:13][O:14][C:15]1[C:16]([F:50])=[C:17]([CH:23]([NH:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]3[N:48]=[C:47]([CH3:49])[O:46][N:45]=3)=[CH:40][CH:39]=2)[C:24]2[NH:28][C:27](=[O:29])[N:26]([C:30]3[C:31](=[O:36])[NH:32][CH:33]=[CH:34][N:35]=3)[N:25]=2)[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1)(C(C)(C)C)(C)C>[Fe].C(O)(=O)C>[C:47]([OH:2])(=[O:46])[CH3:49].[F:50][C:16]1[C:15]([O:14][CH2:13][CH2:12][OH:11])=[CH:20][C:19]([O:21][CH3:22])=[CH:18][C:17]=1[CH:23]([NH:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]([NH2:48])=[NH:45])=[CH:40][CH:39]=1)[C:24]1[NH:28][C:27](=[O:29])[N:26]([C:30]2[C:31](=[O:36])[NH:32][CH:33]=[CH:34][N:35]=2)[N:25]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Iron powder (55 mg) was added to 4.5 ml of a methanol:water:acetic acid=1:1:1 mixed solvent solution containing 34 mg of 3-(3-{{3-[2-(t-butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-1H-[1,2,4]triazol-1-yl)-1H-pyrazin-2-one. The mixture was stirred at 65° C. for 24 hours under a nitrogen atmosphere. The reaction mixture was filtered and then purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid) to give 4-({[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-[5-oxo-1-(3-oxo-3,4-dihydropyrazin-2-yl)-4,5-dihydro-1H-[1,2,4]triazol-3-yl]methyl}amino)benzamidine acetate (5.9 mg).

Workup

filtrationThe reaction mixture was filtered
custompurified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% acetic acid)

Sources & evidence

ORD record: ord-8ecab216a6184c9ba05112d9a6c96a67
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816522B2

Reaction notes

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