HCID 89876084, compound → HCID 72194937, compound

HRID 594173Notes

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][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]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]([CH3:31])[CH3:32])=[CH:26][N:25]=2)(=[O:17])=[O:18])=[CH:12][CH:11]=1)[CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 2-(4-(1-hydroxy-2-morpholinoethyl)-N-isobutylphenylsulfonamido)-5-isopropylpyridine 1-oxide (130 mg, 0.272 mmol) in ethanol (1 mL) at 20° C. was added molybdenum hexacarbonyl (71.9 mg, 0.272 mmol). The reaction vessel was sealed and heated by microwaves to 150° C. for 1 hour. After cooling, the reaction was filtered and evaporated in vacuo to give the crude product. The crude was purified by mass directed autoprep (ammonium carbonate modifier) but gave impure product. The sample was repurified by mass directed autoprep (formic acid modifier) to give the title product, 34.1 mg. LCMS (2 min, formic) Rt 0.85 min, m/z (ES+) 462 (M+H).

Workup

customThe reaction vessel was sealed
temperatureAfter cooling
filtrationthe reaction was filtered
customevaporated in vacuo
customto give the crude product
customThe crude was purified by mass
customgave impure product
customThe sample was repurified by mass

Sources & evidence

ORD record: ord-3ed377b21468454d983658911b63b530
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242972B2

Reaction notes

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