1,4-Dioxane hydrochloride → HCID 69432380, compound

HRID 1269987Notes

Reaction equation

HRID 1269987 reaction equation
[CH3:1][N:2]([C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][C:16]2[C:17]([CH3:31])=[C:18]3[C:22](=[CH:23][CH:24]=2)[N:21](C2CCCCO2)[N:20]=[CH:19]3)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.O1CCOCC1>C(O)(C)C>[CH3:1][N:2]([C@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([O:15][C:16]2[C:17]([CH3:31])=[C:18]3[C:22](=[CH:23][CH:24]=2)[NH:21][N:20]=[CH:19]3)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69433099HCID 69433099, compound

Product 1

HCID 69432380HCID 69432380, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Under nitrogen, N-methyl-N-[cis-3-[(4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)oxy]cyclohexyl]-N-phenylamine (89 mg, 0.212 mmol) was dissolved in isopropyl alcohol (4 ml), followed by adding thereto a 4N-hydrochloric acid/1,4-dioxane solution (4 ml), and the resulting mixture was stirred at room temperature for 22 hours. The solvent was distilled off under reduced pressure, and the residue was neutralized with aqueous ammonia and concentrated to dryness under reduced pressure. The resulting concentration residue was purified by a silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1) to obtain N-methyl-N-[cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl]-N-phenylamine (62 mg, yield 87.1%) as a white amorphous substance.

Workup

  1. additionby adding
  2. distillationThe solvent was distilled off under reduced pressure
  3. concentrationconcentrated to dryness under reduced pressure
  4. concentrationThe resulting concentration residue
  5. customwas purified by a silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-94ec789fcab64ab3b498872a4dda1e8d
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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