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

HRID 1161566Notes

Reaction equation

C[OH:2].O.[Si]([O:11][CH2:12][CH2:13][O:14][C:15]1[C:16]([F:52])=[C:17]([CH:23]([NH:39][C:40]2[CH:45]=[CH:44][C:43]([C:46]3[N:50]=[C:49]([CH3:51])[O:48][N:47]=3)=[CH:42][CH:41]=2)[C:24]2[NH:25][C:26](=[O:38])[N:27]([C:29]3[C:34]([N+:35]([O-])=O)=[CH:33][CH:32]=[CH:31][N:30]=3)[N:28]=2)[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1)(C(C)(C)C)(C)C>[Fe].C(O)(=O)C>[C:49]([OH:2])(=[O:48])[CH3:51].[NH2:35][C:34]1[C:29]([N:27]2[C:26](=[O:38])[NH:25][C:24]([CH:23]([NH:39][C:40]3[CH:41]=[CH:42][C:43]([C:46]([NH2:50])=[NH:47])=[CH:44][CH:45]=3)[C:17]3[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=[C:15]([O:14][CH2:13][CH2:12][OH:11])[C:16]=3[F:52])=[N:28]2)=[N:30][CH:31]=[CH:32][CH:33]=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 55 mg of 5-{{3-[2-(t-butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-2-(3-nitropyridin-2-yl)-2,4-dihydro-[1,2,4]triazol-3-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 the title compound (21 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-fa6bf3caef6247a69ffb4f3572fa4367
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816522B2

Reaction notes

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