Imidazole → HCID 11441884, compound

HRID 2216310Notes

Reaction equation

HRID 2216310 reaction equation
[H-].[Na+].F[C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[C:14]([NH:20][C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[CH3:29])=[N:15][C:16]([CH3:19])=[N:17][CH:18]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1.[NH4+].[Cl-]>O1CCOCC1>[N:30]1([C:4]2[CH:9]=[CH:8][C:7]([S:10]([C:13]3[C:14]([NH:20][C:21]4[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=4[CH3:29])=[N:15][C:16]([CH3:19])=[N:17][CH:18]=3)(=[O:12])=[O:11])=[CH:6][CH:5]=2)[CH:34]=[CH:33][N:32]=[CH:31]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 11485961HCID 11485961, compound

Product 1

HCID 11441884HCID 11441884, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sodium hydride (60% in oil, 32 mg, 0.78 mmol) was added to a solution of [5-(4-fluoro-benzenesulfonyl)-2-methylpyrimidin-4-yl]-(2,4,6-trimethylphenyl)-amine (100 mg, 0.26 mmol) and imidazole (53 mg, 0.78 mmol) in 1,4-dioxane (4 mL). The mixture was stirred at room temperature for 10 min and then heated at reflux under N2 for 24 h. The mixture was cooled to room temperature, and saturated aqueous NH4Cl was added. The mixture was extracted three times with CH2Cl2, and the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (EtOAc) to provide the target compound (56 mg, 50%) as a white solid: mp 230–232° C.; 1H NMR (500 MHz, DMSO-d6) δ 8.82 (s, 1H), 8.48 (br s, 1H), 8.44 (s, 1H), 8.34 (d, J=8.7 Hz, 2H), 7.95 (d, J=8.7 Hz, 2H), 7.90 (s, 1H), 7.15 (s, 1H), 6.89 (s, 2H), 2.25 (s, 3H), 2.24 (s, 3H), 1.86 (s, 6H); APCI MS m/z 434 [(M+H)+, calcd for C23H24N5O2S, 434.1].

Workup

  1. temperatureheated
  2. temperatureat reflux under N2 for 24 h
  3. temperatureThe mixture was cooled to room temperature
  4. extractionThe mixture was extracted three times with CH2Cl2
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel (EtOAc)

Sources & evidence

ORD record
ord-a2e0a4adb87d490e850787db611833f8
Source dataset
uspto-grants-2006_09
Patent number
US07112585B2

Reaction notes

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