HCID 89875888, compound → HCID 72194938, compound

HRID 594174Notes

Reaction equation

[OH:1][CH:2]([C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]([C:24]2[CH:29]=[CH:28][C:27]([CH:30]([CH3:32])[CH3:31])=[CH:26][N+:25]=2[O-])[CH2:20][CH:21]([CH3:23])[CH3:22])(=[O:18])=[O:17])=[CH:12][CH:11]=1)[CH2:3][NH:4][C:5]1([CH3:9])[CH2:8][O:7][CH2:6]1>C(O)C.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[OH:1][CH:2]([C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:24]2[CH:29]=[CH:28][C:27]([CH:30]([CH3:32])[CH3:31])=[CH:26][N:25]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1)[CH2:3][NH:4][C:5]1([CH3:9])[CH2:8][O:7][CH2:6]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-(4-(1-hydroxy-2-((3-methyloxetan-3-yl)amino)ethyl)-N-isobutylphenylsulfonamido)-5-isopropylpyridine 1-oxide (71.9 mg, 0.151 mmol), in ethanol (1 mL) stirred in air at 20° C., was added molybdenum hexacarbonyl (39.7 mg, 0.151 mmol). The reaction was heated by microwaves to 100° C. for 10 minutes. After cooling, the reaction mixture was filtered and solids washed with ethanol (5 mL) and dichloromethane (5 mL). The combined filtrate was evaporated in vacuo and the crude sample purified by mass directed autoprep (ammonium carbonate modifier). The relevant fractions were concentrated under a stream of nitrogen to give the title product, 7.5 mg. LCMS (2 min, formic) Rt 0.91 min, m/z (ES+) 462 (M+H).

Workup

temperatureAfter cooling
filtrationthe reaction mixture was filtered
washsolids washed with ethanol (5 mL) and dichloromethane (5 mL)
customThe combined filtrate was evaporated in vacuo
customthe crude sample purified by mass
concentrationThe relevant fractions were concentrated under a stream of nitrogen

Sources & evidence

ORD record: ord-3487c4ba2a2841b38254419b14f526db
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242972B2

Reaction notes

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