Water → HCID 136253986, compound

HRID 1043950Notes

Reaction equation

HRID 1043950 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:24]([CH3:25])=[CH:23][N:22]=[C:21]([O:26][CH3:27])[C:20]=4[CH3:28])=[CH:15][C:14]=3[N+:29]([O-])=O)=[C:11]([C:32]([O:34]CC)=O)[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:4]1[CH2:5][CH:6]([N:8]2[C:12]3[C:13]4[CH:18]=[CH:17][C:16]([C:19]5[C:24]([CH3:25])=[CH:23][N:22]=[C:21]([O:26][CH3:27])[C:20]=5[CH3:28])=[CH:15][C:14]=4[NH:29][C:32](=[O:34])[C:11]=3[CH:10]=[N:9]2)[CH2:7][O:1][CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 86686380ethyl 1-(1,4-dioxepan-6-yl)-5-[4-(2-methoxy-3,5-dimethylpyridin-4-yl)-2-nitrophenyl]-1H-pyrazole-4-carboxylate

Product 1

HCID 136253986HCID 136253986, compoundYield 53.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Iron powder (28.8 mg) was added to a solution of ethyl 1-(1,4-dioxepan-6-yl)-5-[4-(2-methoxy-3,5-dimethylpyridin-4-yl)-2-nitrophenyl]-1H-pyrazole-4-carboxylate (64 mg) in acetic acid (2 mL)-water (0.1 mL), and the reaction mixture was stirred at 80° C. for 2.5 hours in a nitrogen atmosphere. The reaction mixture was returned to room temperature, and ethyl acetate (10 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. The filtrate was passed through a NH silica gel pad. The resulting solution was concentrated under reduced pressure. Ethyl acetate (0.3 mL) and MTBE (0.3 mL) were added to the residue. The precipitated solid was collected by filtration to give the title compound (29.1 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. concentrationThe resulting solution was concentrated under reduced pressure
  8. additionEthyl acetate (0.3 mL) and MTBE (0.3 mL) were added to the residue
  9. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-25270a2b83a64e53a67217c74bc9a84d
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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