Water → 1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-one

HRID 512830Notes

Reaction equation

HRID 512830 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[N:11][C:10]([N:13]3[CH2:22][CH2:21][C:16]4(OCC[O:17]4)[CH2:15][CH2:14]3)=[CH:9][CH:8]=2)[CH:4]=[N:3]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>CC(C)=O.O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[N:11][C:10]([N:13]3[CH2:22][CH2:21][C:16](=[O:17])[CH2:15][CH2:14]3)=[CH:9][CH:8]=2)[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 896143308-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)-1,4-dioxa-8-azaspiro[4.5]decane

Product 1

HCID 896139951-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-one

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
65 °C

Procedure

To a solution of 8-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)-1,4-dioxa-8-azaspiro[4.5]decane, prepared as in STEP 2 above (1.8 g, 6 mmol) in acetone/H2O (30 mL/30 mL) was added p-TSA.H2O (1.37 g, 7.2 mmol). The resulting mixture was stirred at 65° C. for 6 h and then concentrated to remove most of organic solvent. The residue was poured into CH2Cl2/H2O/Na2CO3(aq) (50 mL/25 mL/25 mL). The aqueous layer was extracted with CH2Cl2 (50 mL). The combined organic layer was dried (Na2SO4), and filtered. The solvent was removed by roto-evaporator to yield 1-(6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3-yl)piperidin-4-one as a solid.

Workup

  1. concentrationconcentrated
  2. customto remove most of organic solvent
  3. additionThe residue was poured into CH2Cl2/H2O/Na2CO3(aq) (50 mL/25 mL/25 mL)
  4. extractionThe aqueous layer was extracted with CH2Cl2 (50 mL)
  5. dry with materialThe combined organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customThe solvent was removed by roto-evaporator

Sources & evidence

ORD record
ord-10090d5e173e47dd946086cf3c303c49
Source dataset
uspto-grants-2015_08
Patent number
US09102669B2

Reaction notes

Loading…