Imidazole → HCID 68561331, compound

HRID 1517344Notes

Reaction equation

HRID 1517344 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].N1[CH:11]=[CH:10]N=C1.[CH3:12][S:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[CH:30]=[C:29]([O:31][CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[N:28]=[CH:27][N:26]=1)[CH2:20][CH2:19]2)(=[O:15])=[O:14].[Cl-].[NH4+]>O1CCOCC1>[CH3:12][S:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[N:26]=[CH:27][N:28]=[C:29]([O:31][CH:32]3[CH2:37][CH2:36][N:35]([C:1]([O:2][C:10]4([CH3:11])[CH2:23][CH2:24][CH2:16][CH2:17]4)=[O:4])[CH2:34][CH2:33]3)[CH:30]=1)[CH2:20][CH2:19]2)(=[O:15])=[O:14]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 667096685-(Methylsulfonyl)-1-(6-(piperidin-4-yloxy)pyrimidin-4-yl)indoline

Product 1

HCID 68561331HCID 68561331, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Potassium carbonate (153 mg, 1.11 mmol) and the imidazole compound (129 mg, 0.665 mmol) were added to a dioxane (10 mL) solution of the 5-(methylsulfonyl)-1-[6-(piperidin-4-yloxy)pyrimidin-4-yl]indoline (82.9 mg, 0.222 mmol) produced in Reference Example 28, and the mixture was heated to reflux for 8 hours. To the reaction solution, a saturated aqueous solution of ammonium chloride was added, followed by extraction with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-3:2, V/V) to obtain the title compound as white powder (46.8 mg, yield: 42%).

Workup

  1. customproduced in Reference Example 28
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 8 hours
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-3:2, V/V)

Sources & evidence

ORD record
ord-bd5d3a2496b14948b6edfd3cb799303a
Source dataset
uspto-grants-2012_07
Patent number
US08232287B2

Reaction notes

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