Water → HCID 136383505, compound

HRID 2110581Notes

Reaction equation

HRID 2110581 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:15]OC)([CH2:12][CH2:13][CH3:14])[C:4](=[O:18])[C:3]=1[C:19]1[NH:24][C:23]2[CH:25]=[CH:26][C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][C:22]=2[S:21](=[O:35])(=[O:34])[N:20]=1.O>CC#N.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[NH2:15][C:5]1([CH2:12][CH2:13][CH3:14])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([OH:1])=[C:3]([C:19]2[NH:24][C:23]3[CH:25]=[CH:26][C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][C:22]=3[S:21](=[O:35])(=[O:34])[N:20]=2)[C:4]1=[O:18]

Participants

5

Reactant 2

HCID 962WaterHCID 136383506HCID 136383506, compound

Product 1

HCID 136383505HCID 136383505, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of the product of Example 9 (20 mg, 0.038 mmol) in CH3CN (1.5 mL) was added H2O (100 uL) and molybdenum hexacarbonyl (7 mg, 0.027 mmol) and the solution was refluxed for 2 hours. After cooling to room temperature the solvent was removed in vacuo and the crude product was purified by column chromatography on C-1 8 silica gel (70:30:0.1 methanol:H2O:trifluoroacetic acid) to give the title compound as a colorless solid (13 mg, 69%): 1H NMR (d6-DMSO) δ 14.47 (s, 1H), 9.94 (s, 1H), 8.61 (s, 2H), 8.14, 8.11 (d, 1H), 7.70-7.42 (m, 5H), 7.37, 7.34 (d, 1H), 3.01 (s, 3H), 2.03-1.93 (m, 1H), 1.87-1.75 (m, 1H), 1.29-1.14 (m, 1H), 0.96-0.83 (m, 1H), 0.76-0.67 (t, 3H); MS (ESI) m/z 491 (M+H+).

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. customwas removed in vacuo
  3. customthe crude product was purified by column chromatography on C-1 8 silica gel (70:30:0.1 methanol:H2O:trifluoroacetic acid)

Sources & evidence

ORD record
ord-b0aab33e173143b99c31625f35d91e45
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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