Water → HCID 11757792, compound

HRID 374069Notes

Reaction equation

HRID 374069 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:50])[N:11]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[N:26](COCC[Si](C)(C)C)[C:27]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:29]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:50])[N:11]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[NH:29][C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:27]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:26]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 11765306HCID 11765306, compound

Product 1

HCID 11757792HCID 11757792, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part D. To a solution of N'-(2,4-difluorophenyl)-N-[6-(4,5-diphenyl-1-[(trimethylsilyl)ethoxymethyl]-1H-imidazol-2-yl)hexyl]-N-heptylurea (0.60 g, 0.000853 mol) in dry tetrahydrofuran (10 mL) under a nitrogen atmosphere, tetrabutylammonium fluoride (1M in tetrahydrofuran, 3.41 mL) was added and the reaction mixture was heated to reflux 7 hours. The reaction mixture was cooled, poured into water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with water, brine, dried over magnesium sulfate and concentrated in vacuo. The product was purified by flash chromatography on silica gel (75 mL) eluting hexane:ethyl acetate (60:40 v:v) to give the title compound as a colorless glass (0.26 g, 0.000454 mol). 1H NMR (CDCl3) δ9.5-9.0(bs,1H), 7.87(m,1H), 7.5-7.2(m,10H), 6.83-6.7(m,2H), 6.4(d,1H), 3.28(m,4H), 2.67(t,2H), 1.75-1.26(m,18H), 0.88(t,3H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux 7 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. washThe combined organic layer was washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by flash chromatography on silica gel (75 mL)
  9. washeluting hexane:ethyl acetate (60:40 v:v)

Sources & evidence

ORD record
ord-316f5b8511014a20a101065c21f6a424
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Reaction notes

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