N-[1-(cyanomethyl-carbamoyl)-cyclohexyl]-4-bromomethyl-benzamide → N-[1-(cyanomethyl-carbamoyl)-cyclohexyl]-4-imidazol-1-ylmethyl-benzamide

HRID 276707Notes

Reaction equation

HRID 276707 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C:7]1([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([CH2:21]Br)=[CH:17][CH:16]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2].[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1.[Na]>C1COCC1>[C:1]([CH2:3][NH:4][C:5]([C:7]1([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:24]3[CH:28]=[CH:27][N:26]=[CH:25]3)=[CH:17][CH:16]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2]

Participants

4

Reactant 2

HCID 18316675N-[1-(cyanomethyl-carbamoyl)-cyclohexyl]-4-bromomethyl-benzamideHCID 57373095Imidazole sodium

Product 1

HCID 18316729N-[1-(cyanomethyl-carbamoyl)-cyclohexyl]-4-imidazol-1-ylmethyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[1-(cyanomethyl-carbamoyl)-cyclohexyl]-4-bromomethyl-benzamide (0.34 mmol) is dissolved in THF (2 ml) and sodium-imidazol (0.41 mmol) is added and the reaction mixture stirred at RT over night. After evaporation of the solvent, the residue is extracted with ethyl acetate. The extract is washed with water, dried over magnesium sulfate and evaporated. The residue was suspended in diethylether and the solid filtered of. The crude product is purified by chromatography on silica using CH2Cl2/MeOH=9:1. The fractions containing the pure product were collected and evaporated. The residue was suspended in diethylether and the solid filtered of. A white powder with mp. 194-196° C., Rf=0.28 (CH2Cl2/MeOH=9:1) is obtained.

Workup

  1. customAfter evaporation of the solvent
  2. extractionthe residue is extracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. filtrationthe solid filtered of
  7. customThe crude product is purified by chromatography on silica
  8. additionThe fractions containing the pure product
  9. customwere collected
  10. customevaporated
  11. filtrationthe solid filtered of
  12. customA white powder with mp. 194-196° C., Rf=0.28 (CH2Cl2/MeOH=9:1) is obtained

Sources & evidence

ORD record
ord-af7c57917eba45069de235d26c3be861
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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