Water → (S)-7-(6-isopropyloxy-2,4-dimethylpyridin-3-yl)-1-(tetrahydrofuran-3-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-one

HRID 1043955Notes

Reaction equation

HRID 1043955 reaction equation
[CH:1]([O:4][C:5]1[N:10]=[C:9]([CH3:11])[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:22]([C@H:23]4[CH2:27][CH2:26][O:25][CH2:24]4)[N:21]=[CH:20][C:19]=3[C:28]([O:30]CC)=O)=[C:14]([N+:33]([O-])=O)[CH:13]=2)=[C:7]([CH3:36])[CH:6]=1)([CH3:3])[CH3:2].O.C(OCC)(=O)C>C(O)(=O)C.[Fe]>[CH:1]([O:4][C:5]1[N:10]=[C:9]([CH3:11])[C:8]([C:12]2[CH:17]=[CH:16][C:15]3[C:18]4[N:22]([C@H:23]5[CH2:27][CH2:26][O:25][CH2:24]5)[N:21]=[CH:20][C:19]=4[C:28](=[O:30])[NH:33][C:14]=3[CH:13]=2)=[C:7]([CH3:36])[CH:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 86686386ethyl 5-[4-(6-isopropyloxy-2,4-dimethylpyridin-3-yl)-2-nitrophenyl]-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylate

Product 1

HCID 136253984(S)-7-(6-isopropyloxy-2,4-dimethylpyridin-3-yl)-1-(tetrahydrofuran-3-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-oneYield 63.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of ethyl 5-[4-(6-isopropyloxy-2,4-dimethylpyridin-3-yl)-2-nitrophenyl]-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylate (65.1 mg) in acetic acid (1.5 mL)-water (0.15 mL) was stirred at 80° C. for 15 minutes. Iron powder (45.1 mg) was added to the solution, and the mixture was stirred at the same temperature for two 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 washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was suspended and triturated by adding MTBE. The precipitated solid was collected by filtration to give the title compound (35.1 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 washed with a saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customtriturated
  9. additionby adding MTBE
  10. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-da2c1d77db3f401da79587fe3726fc64
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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