Hydrochloric Acid → HCID 57420550, compound

HRID 1723839Notes

Reaction equation

HRID 1723839 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>CCOC(C)=O>[ClH:30].[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([N:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]([O:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[N:16]2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 685301764-[1-(4-chloro-phenyl)-1H-indazol-3-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 57420550HCID 57420550, compoundYield 171.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Intermediate 42 (212 mg, 0.495 mmol) was dissolved in EtOAc (2 ml), treated with 4M HCl in dioxane (1.61 ml, 6.44 mmol) and stirred overnight at room temperature. The mixture was concentrated in vacuo, treated with EtOAc and concentrated again. This process was repeated 5 times. The resulting white solid was triturated with Et2O, filtered, rinsed with Et2O and dried in a vacuum oven at 50° C. to afford 155 mg (86%) of the title product—1-(4-chloro-phenyl)-3-(piperidin-4-yloxy)-1H-indazole hydrochloride as a white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiontreated with EtOAc
  3. concentrationconcentrated again
  4. customThe resulting white solid was triturated with Et2O
  5. filtrationfiltered
  6. washrinsed with Et2O
  7. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-2958750a3cb1460582c7455972d3285f
Source dataset
uspto-grants-2009_02
Patent number
US07485636B2

Reaction notes

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