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

HRID 1161570Notes

Reaction equation

C[OH:2].O.[F:4][C:5]1[C:10]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[CH:9][C:8]([O:16][CH3:17])=[CH:7][C:6]=1[CH:18]([NH:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[N:45]=[C:44]([C:46](F)(F)F)[O:43][N:42]=2)=[CH:37][CH:36]=1)[C:19]1[NH:20][C:21](=[O:33])[N:22]([C:24]2[C:29]([N+:30]([O-])=O)=[CH:28][CH:27]=[CH:26][N:25]=2)[N:23]=1>[Fe].C(O)(=O)C>[C:44]([OH:2])(=[O:43])[CH3:46].[NH2:30][C:29]1[C:24]([N:22]2[C:21](=[O:33])[NH:20][C:19]([CH:18]([NH:34][C:35]3[CH:36]=[CH:37][C:38]([C:41]([NH2:45])=[NH:42])=[CH:39][CH:40]=3)[C:6]3[CH:7]=[C:8]([O:16][CH3:17])[CH:9]=[C:10]([O:11][CH2:12][CH2:13][O:14][CH3:15])[C:5]=3[F:4])=[N:23]2)=[N:25][CH:26]=[CH:27][CH:28]=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 38 mg of 5-{[2-fluoro-5-methoxy-3-(2-methoxyethoxy)phenyl]-[4-(5-trifluoromethyl-[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 (25 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-58daea2d35444d7ba34990eceeaed239
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816522B2

Reaction notes

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