Triethylamine → HCID 86688150, compound

HRID 1428946Notes

Reaction equation

HRID 1428946 reaction equation
CS(Cl)(=O)=O.[CH2:6]([N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([CH3:20])[CH:14]=2)[N:10]=[C:9]1[CH2:21]O)[CH3:7].[CH2:23]([N:25](CC)CC)C.[C-]#N.[K+]>O1CCCC1>[CH2:6]([N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[C:15]([CH3:20])[CH:14]=2)[N:10]=[C:9]1[CH2:21][C:23]#[N:25])[CH3:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9032Potassium Cyanide2×HCID 31297Methanesulfonyl chlorideHCID 86688151HCID 86688151, compound

Product 1

HCID 86688150HCID 86688150, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

870 μL methanesulfonyl chloride was added to 2.5 g (1-ethyl-4-(4-fluoro-3-methyl-phenyl)-1H-imidazol-2-yl)-methanol and 1.85 mL triethylamine in 50 mL tetrahydrofuran. The reaction was stirred 1 h at RT and 1.4 g potassium cyanide was added and stiffing was continued for 3 h. Then 1.4 g potassium cyanide and 500 mg dibenzo-18-crone-6 was added and the reaction was stirred over night at RT. The mixture was filtered and evaporated. Dichlormethane was added to the residue and extracted with aqueous potassium carbonate solution. The organic layer was dried and evaporated. The residue was purified by chromatographie on silica gel (cyclohexane/ethyl acetate 3:2) to yield 533 mg of the desired product. Rt: 1.29 min (method K), (M+H)+: 244

Workup

  1. waitstiffing was continued for 3 h
  2. stirringthe reaction was stirred over night at RT
  3. filtrationThe mixture was filtered
  4. customevaporated
  5. additionDichlormethane was added to the residue
  6. extractionextracted with aqueous potassium carbonate solution
  7. customThe organic layer was dried
  8. customevaporated
  9. customThe residue was purified by chromatographie on silica gel (cyclohexane/ethyl acetate 3:2)

Sources & evidence

ORD record
ord-deba2c27be6b4b17b74c07c58ed8480a
Source dataset
uspto-grants-2015_01
Patent number
US08937176B2

Reaction notes

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