Water → HCID 136253987, compound

HRID 1043952Notes

Reaction equation

HRID 1043952 reaction equation
[O:1]1[CH2:7][CH:6]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[C:20]([O:27][CH3:28])=[N:21][C:22]([CH3:26])=[CH:23][C:24]=4[CH3:25])=[CH:15][C:14]=3[N+:29]([O-])=O)=[C:11]([C:32](OCC)=[O:33])[CH:10]=[N:9]2)[CH2:5][O:4][CH2:3][CH2:2]1.O.C(OCC)(=O)C>C(O)(=O)C.[Fe]>[O:1]1[CH2:7][CH:6]([N:8]2[C:12]3[C:13]4[CH:18]=[CH:17][C:16]([C:19]5[C:20]([O:27][CH3:28])=[N:21][C:22]([CH3:26])=[CH:23][C:24]=5[CH3:25])=[CH:15][C:14]=4[NH:29][C:32](=[O:33])[C:11]=3[CH:10]=[N:9]2)[CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 86686381HCID 86686381, compound

Product 1

HCID 136253987HCID 136253987, compoundYield 11.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Iron powder (17 mg) was added to a solution of ethyl 1-(1,4-dioxepan-6-yl)-5-{4-(2-methoxy-4,6-dimethylpyridin-3-yl)-2-nitrophenyl}-1H-pyrazole-4-carboxylate (15 mg) in acetic acid (1 mL)-water (0.05 mL), and the mixture was stirred at 80° C. for 4.25 hours in a nitrogen atmosphere. The reaction mixture was returned to room temperature, and ethyl acetate (5 mL) was added to the reaction mixture. The insoluble matter was removed by filtration through Celite™. The filtrate was concentrated under reduced pressure. A solution of the residue in ethyl acetate was sequentially washed with a saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by preparative thin-layer chromatography (silica gel, ethyl acetate/n-heptane, 66%) to give the title compound (1.5 mg).

Workup

  1. customwas returned to room temperature
  2. customThe insoluble matter was removed by filtration through Celite™
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washA solution of the residue in ethyl acetate was sequentially washed with a saturated aqueous sodium bicarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by preparative thin-layer chromatography (silica gel, ethyl acetate/n-heptane, 66%)

Sources & evidence

ORD record
ord-4dda0817082346e29787d7fd59e3f20d
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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