Acetone → HCID 178459943, compound

HRID 1433225Notes

Reaction equation

HRID 1433225 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:31]=[CH:30][C:14]2[NH:15][C:16]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[N:17][C:13]=2[CH:12]=1)(=[O:4])=[O:3].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:42][C:43]([CH3:45])=[O:44].CO>C1COCC1>[CH3:42][C:43]([OH:44])([CH3:45])[CH2:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:31]=[CH:30][C:14]2[NH:15][C:16]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][CH:21]=3)=[N:17][C:13]=2[CH:12]=1)(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 2733832Lithium HexamethyldisilazideHCID 178504705HCID 178504705, compound

Product 1

HCID 178459943HCID 178459943, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(2-methanesulfonyl-phenyl)-2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazole (0.030 g, 0.0671 mmol) in THF (3 mL) was added lithium bis(trimethylsilyl)amide (0.20 mL, 0.201 mmol, 1.0 M solution in THF) at −78° C. After stirring for 30 min, acetone (0.2 mL) was added. The mixture was further stirred another 30 min. followed by an addition of MeOH to quench the reaction. Solvent evaporation provided a residue, which was purified by chromatography (silica, hexanes: EtOAc, 1:2) to afford the title compound as a white solid (0.030 g, 88%). 1H NMR (400 MHz, CD3OD) δ (ppm): 8.19 (dd, 1H, J=8.0 Hz, J=1.2 Hz), 7.75-7.70 (m, 2H), 7.66-7.62 (m, 4H), 7.46 (dd, 1H, J=8.0 Hz, J=1.2 Hz), 7.35 (d, 1H, J=7.6 Hz), 7.25 (d, 2H, J=8.8 Hz), 5.46 (s, 2H), 2.92 (s, 2H), 1.08 (s, 6H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C25H24F3N2O4S: 505.5 (M+H), Found 505.3.

Workup

  1. stirringThe mixture was further stirred another 30 min.
  2. customto quench
  3. customthe reaction
  4. customSolvent evaporation
  5. customprovided a residue, which
  6. customwas purified by chromatography (silica, hexanes: EtOAc, 1:2)

Sources & evidence

ORD record
ord-35f9fa3245704a45b690da1d2ada568f
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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