Acetic Acid → HCID 135982116, compound

HRID 1161533Notes

Reaction equation

[F:1][C:2]1[C:12]2[O:11][CH2:10][CH2:9][CH2:8][O:7][C:6]=2[C:5]([O:13][CH3:14])=[CH:4][C:3]=1[CH:15]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([C:38](=[NH:41])[NH:39]O)=[CH:34][CH:33]=1)[C:16]1[NH:20][C:19](=[O:21])[N:18]([C:22]2[N:30]=[CH:29][CH:28]=[CH:27][C:23]=2[C:24]([OH:26])=[O:25])[N:17]=1.O.C(O)(=O)C>CO.[Fe]>[C:38]([C:35]1[CH:36]=[CH:37][C:32]([NH:31][CH:15]([C:3]2[CH:4]=[C:5]([O:13][CH3:14])[C:6]3[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]=3[C:2]=2[F:1])[C:16]2[NH:20][C:19](=[O:21])[N:18]([C:22]3[N:30]=[CH:29][CH:28]=[CH:27][C:23]=3[C:24]([OH:26])=[O:25])[N:17]=2)=[CH:33][CH:34]=1)(=[NH:39])[NH2:41]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 61 mg of 2-(3-{(6-fluoro-9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-[4-(N-hydroxycarbamimidoyl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)nicotinic acid in 6 ml of a methanol:water:acetic acid=1:1:1 mixed solvent there was added 60 mg of iron powder, and the mixture was stirred at 60° C. for 30 hours under a nitrogen atmosphere. Upon cooling, the reaction mixture was filtered through celite and purified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% trifluoroacetic acid) to give 2-{3-[(4-carbamimidoylphenylamino)-(6-fluoro-9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}nicotinic acid.

Workup

temperatureUpon cooling
filtrationthe reaction mixture was filtered through celite
custompurified by reverse-phase high performance liquid chromatography (acetonitrile-water, 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-1dfbb59423e941789307c8ca63a4972d
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816522B2

Reaction notes

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