Imidazole → HCID 10270384, compound

HRID 2101683Notes

Reaction equation

HRID 2101683 reaction equation
Cl[C:2]1[N:3]([CH3:19])[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.C([Li])CCC.Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27].N1C=CN=C1>O1CCCC1>[C:7]1([C:5]2[N:6]=[C:2]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])[N:3]([CH3:19])[C:4]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 10387Benzyl chloroformate2×HCID 12675129HCID 12675129, compoundHCID 178418339Butyllithium

Product 1

HCID 10270384HCID 10270384, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 2-chloro-4,5-diphenyl-1-methylimidazole (1.46 g, 5.4 mmol) from Step B in tetrahydrofuran (THF) (20 mL) under nitrogen was cooled to −70° C. in a dry ice/acetone bath. n-Butyl lithium (1.6 N in hexanes, 10.2 mL, 16.3 mmol) was added via syringe. The reaction was allowed to warm to −20° C. for 2 hr. In a separate round-bottomed flask, a solution of benzyl chloroformate (CBZ-Cl) (4.3 mL, 16.3 mmol) in TBF (10 mL) was cooled to −20° C. The above imidazole reaction was added via a double-tipped needle to the solution of CBZ-Cl and after 20 min the reaction was allowed to warm to rt for 30 min. The reaction was then quenched into an aqueous sodium bicarbonate solution and was then extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate and evaporated. The residue was purified by flash chromatography (5% methylene chloride and 15% ethyl acetate in hexanes) to afford the title compound.

Workup

  1. temperatureto warm to rt for 30 min
  2. customThe reaction was then quenched into an aqueous sodium bicarbonate solution
  3. extractionwas then extracted twice with ethyl acetate
  4. washThe organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by flash chromatography (5% methylene chloride and 15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ba0b7c2101cc4bb6b215861e5eb0ae4c
Source dataset
uspto-grants-2009_08
Patent number
US07572785B2

Reaction notes

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