1,4-Dioxane hydrochloride → HCID 69431158, compound

HRID 1269980Notes

Reaction equation

HRID 1269980 reaction equation
[CH3:1][C:2]1[C:10]([O:11][C@H:12]2[CH2:17][CH2:16][CH2:15][C@@H:14]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:13]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2C1CCCCO1.[ClH:29].O1CCOCC1>C(O)(C)C>[ClH:29].[CH3:1][C:2]1[C:10]([O:11][C@H:12]2[CH2:17][CH2:16][CH2:15][C@@H:14]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:13]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 69434092HCID 69434092, compound

Product 1

HCID 69431158HCID 69431158, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Under nitrogen, the 4-methyl-5-[(cis-3-pyrrolidin-1-ylcyclohexyl)oxy]-1-tetrahydro-2H-pyran-2-yl-1H-indazole (60 mg, 0.156 mmol) obtained in Example 725 was dissolved in isopropyl alcohol (2 ml), followed by adding thereto a 4N-hydrochloric acid/1,4-dioxane solution (2 ml), and the resulting mixture was stirred at room temperature for 3 hours. The solvent was distilled off under reduced pressure and the resulting concentration residue was purified by a silica gel column chromatography (eluent: acetonitrile/aqueous ammonia=100/0, 100/2, 100/4). Then, a 4N-hydrochloric acid/1,4-dioxane solution was added thereto and the solvent was distilled off under reduced pressure to obtain 4-methyl-5-[(cis-3-pyrrolidin-1-ylcyclohexyl)oxy]-1H-indazole monohydrochloride (55 mg, yield 100%) as a hygroscopic light-yellow solid.

Workup

  1. additionby adding
  2. distillationThe solvent was distilled off under reduced pressure
  3. concentrationthe resulting concentration residue
  4. customwas purified by a silica gel column chromatography (eluent: acetonitrile/aqueous ammonia=100/0, 100/2, 100/4)
  5. additionThen, a 4N-hydrochloric acid/1,4-dioxane solution was added
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-06be1d56aaaf414ab2885689b9702521
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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