Ammonia → HCID 178437190, compound

HRID 1694790Notes

Reaction equation

HRID 1694790 reaction equation
CN(C)S([N:6]1[CH:10]=[C:9]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=2[F:20])[CH3:12])[N:8]=[C:7]1[Si](C(C)(C)C)(C)C)(=O)=O.N>Cl>[F:20][C:14]1[C:15]([F:19])=[CH:16][CH:17]=[CH:18][C:13]=1[CH:11]([C:9]1[N:8]=[CH:7][NH:6][CH:10]=1)[CH3:12]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 67277501HCID 67277501, compound

Product 1

HCID 178437190HCID 178437190, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(+)-2-(tert-Butyl-dimethyl-silanyl)-4-[1-(2,3-difluoro-phenyl)-ethyl]-imidazole-1-sulfonic acid dimethylamide (350 mg, 0.81 mmol) was dissolved in 10 ml 1.5N hydrochloric acid and refluxed for 1 h. The cooled solution was adjusted to pH>8 with 25% aqueous ammonia and the solution was extracted with dichloromethane (2 times). The combined organic layers are dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (silica gel, dichloromethane/methanol/aqueous conc. ammonia=90:10:1) to yield 80 mg (47%) of 4-[1-(2,3-difluoro-phenyl)-ethyl]-1H-imidazole (Enantiomer 1) as off-white solid: MS (ISP): 208.9 ((M+H)+.), chiral HPLC (Reprosil Chiral-NR; heptane/ethanol=90:10): tR=9.9 min. 4-[1-(2,3-Difluoro-phenyl)-ethyl]-1H-imidazole (Enantiomer 2) was obtained by the same procedure from (−)-2-(tert-butyl-dimethyl-silanyl)-4-[1-(2,3-difluoro-phenyl)-ethyl]-imidazole-1-sulfonic acid dimethylamide in 73% yield; colourless oil, MS (ISP): 208.9 ((M+H)+.), chiral HPLC (Reprosil Chiral-NR; heptane/ethanol=90:10): tR=11.1 min.

Workup

  1. temperaturerefluxed for 1 h
  2. extractionthe solution was extracted with dichloromethane (2 times)
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica gel, dichloromethane/methanol/aqueous conc. ammonia=90:10:1)

Sources & evidence

ORD record
ord-d70535ed2ab648bbbf46b39650c74e17
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Reaction notes

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