1,4-Dioxane hydrochloride → 5-[(Piperidin-3-yl)oxy]-1H-indazole

HRID 1269809Notes

Reaction equation

HRID 1269809 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][CH:11]3[CH2:16][CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.Cl.O1CCOCC1>CO>[NH:13]1[CH2:14][CH2:15][CH2:16][CH:11]([O:10][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)[CH2:12]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 22933697HCID 22933697, compound

Product 1

HCID 229334705-[(Piperidin-3-yl)oxy]-1H-indazoleYield 101.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the tert-butyl 3-(1H-indazol-5-yloxy)piperidine-1-carboxylate (150 mg, 0.473 mmol) obtained in Example 376 in methanol (2 ml) was added a 4N-hydrochloric acid-dioxane solution (1 ml) at room temperature. After 3 hours, the mixture thus obtained was concentrated under reduced pressure, and the resulting residue was dissolved in methanol. The resulting solution was adjusted to pH 8 to 9 with a 2M-aqueous sodium hydroxide solution and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (eluent: chloroform/methanol/chloroform/methanol/(1%-aqueous ammonia)) to obtain 5-(piperidin-3-yloxy)-1H-indazole (104 mg, 65%).

Workup

  1. customthe mixture thus obtained
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe resulting residue was dissolved in methanol
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by a silica gel column chromatography (eluent: chloroform/methanol/chloroform/methanol/(1%-aqueous ammonia))

Sources & evidence

ORD record
ord-d0b1fc5b89074ca7abb149cf92859a5f
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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