1,4-Dioxane hydrochloride → HCID 178431631, compound

HRID 1269998Notes

Reaction equation

HRID 1269998 reaction equation
[CH3:1][C:2]1[C:10]([O:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2C1CCCCO1.Cl.O1CCOCC1>C(O)(C)C>[CH3:1][C:2]1[C:10]([O:11][C@H:12]2[CH2:13][CH2:14][C@H:15]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:16][CH2:17]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 178431629HCID 178431629, compound

Product 1

HCID 178431631HCID 178431631, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-methyl-5-[(trans-4-pyrrolidin-1-ylcyclohexyl)oxy]-1-tetrahydro-2H-pyran-2-yl-1H-indazole (62.1 mg, 0.162 mmol), a 4N-hydrochloric acid/dioxane solution (2.0 ml) and isopropanol (2.0 ml) was stirred at room temperature for 4 hours. The solvent was distilled off and a 1N-aqueous sodium hydroxide solution (20 ml) was added to the residue, followed by extraction with ethyl acetate (20 ml) (twice). The extract solution was dried over magnesium sulfate and then concentrated to dryness, and the residue oil was purified by elution by a silica gel column chromatography (hexane/ethyl acetate/triethylamine=20:40:3) to obtain 4-methyl-5-[(trans-4-pyrrolidin-1-ylcyclohexyl)oxy]-1H-indazole (28.3 mg, 58%).

Workup

  1. distillationThe solvent was distilled off
  2. additiona 1N-aqueous sodium hydroxide solution (20 ml) was added to the residue
  3. extractionfollowed by extraction with ethyl acetate (20 ml) (twice)
  4. dry with materialThe extract solution was dried over magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customthe residue oil was purified by elution by a silica gel column chromatography (hexane/ethyl acetate/triethylamine=20:40:3)

Sources & evidence

ORD record
ord-f14394cd8f654417ac3aa06a543761ec
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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