Acetyl chloride → HCID 178474522, compound

HRID 1797002Notes

Reaction equation

HRID 1797002 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([CH:14]3[CH2:19][CH2:18][CH:17]([CH2:20][NH2:21])[CH2:16][CH2:15]3)[NH:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.[C:24](Cl)(=[O:26])[CH3:25]>C(Cl)Cl.C1COCC1>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([CH:14]3[CH2:15][CH2:16][CH:17]([CH2:20][NH:21][C:24](=[O:26])[CH3:25])[CH2:18][CH2:19]3)[NH:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 178509631HCID 178509631, compound

Product 1

HCID 178474522HCID 178474522, compound

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

C-{4-[4-(3-trifluoromethyl-phenyl)-1H-imidazole-2-yl]-cyclohexyl}-methylamine (326 mg, 1.0 mmol, from Example 1C) and TEA (102 mg, 1.0 mmol) were dissolved in CH2Cl2/THF (1:1) and brought to 0° C. with an ice bath. Acetyl chloride (79 mg, 1.0 mmol) was added to the reaction mixture slowly and the ice bath was removed. After 2 hours, the solution was diluted with CH2Cl2, added to a separatory funnel and washed with 10% NaOH (3×). The solution was dried (Na2SO4), concentrated under reduced pressure, and the residue purified using flash chromatography (5%→10% MeOH/CH2Cl2) to give (N-{4-[4-(3-Trifluoromethyl-phenyl)-1H-imidazol-2-yl]-cyclohexylmethyl}-acetamide.

Workup

  1. custombrought to 0° C. with an ice bath
  2. customthe ice bath was removed
  3. additionthe solution was diluted with CH2Cl2
  4. additionadded to a separatory funnel
  5. washwashed with 10% NaOH (3×)
  6. dry with materialThe solution was dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customthe residue purified

Sources & evidence

ORD record
ord-21a0a559736843fc81bb646b7a08a814
Source dataset
uspto-grants-2006_04
Patent number
US07034034B2

Reaction notes

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