1,4-Dioxane hydrochloride → HCID 69428495, compound

HRID 1269986Notes

Reaction equation

HRID 1269986 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]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:13]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2C1CCCCO1.COC1C(O[C@@H]2CCC[C@H](NC(=O)CC)C2)=CC=C2C=1C=NN2.Cl.O1CCOCC1>C(O)(C)C>[CH3:1][C:2]1[C:10]([O:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][C@H:14]([N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:13]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2

Participants

5

Reactant 3

HCID 204431481,4-Dioxane hydrochlorideHCID 69433339HCID 69433339, compoundHCID 69435953HCID 69435953, compound

Product 1

HCID 69428495HCID 69428495, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Under nitrogen, the N-[cis-3-[(4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)oxy]cyclohexyl]-N,N-diphenylamine (82 mg, 0.172 mmol) obtained in Example 731, (a) 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 20 hours. The solvent was distilled off under reduced pressure and a saturated aqueous sodium hydrogencarbonate solution was added to the residue, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water and then a saturated aqueous sodium chloride solution, dried by the addition of anhydrous magnesium sulfate, and then filtered. The solvent was distilled off under reduced pressure and the resulting concentration residue was purified by a silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1) to obtain N-[cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl]-N,N-diphenylamine (52 mg, yield 76.8%) as a whitely yellow amorphous substance.

Workup

  1. additionby adding
  2. distillationThe solvent was distilled off under reduced pressure
  3. additiona saturated aqueous sodium hydrogencarbonate solution was added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, dried by the addition of anhydrous magnesium sulfate
  7. filtrationfiltered
  8. distillationThe solvent was distilled off under reduced pressure
  9. concentrationthe resulting concentration residue
  10. customwas purified by a silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-6740fbb3f429461da3611dc343dd1707
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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