N-{1-[(Cyano-dimethyl-methyl)-carbamoyl]-3-methyl-butyl)-4-bromomethyl-benzamide → N-{1-[(Cyano-dimethyl-methyl)-carbamoyl]-3-methyl-butyl}-4-imidazol-1-ylmethyl-benzamide

HRID 276709Notes

Reaction equation

HRID 276709 reaction equation
[C:1]([C:3]([NH:6][C:7]([CH:9]([NH:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([CH2:22]Br)=[CH:18][CH:17]=1)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:8])([CH3:5])[CH3:4])#[N:2].[NH:25]1[CH:29]=[CH:28][N:27]=[CH:26]1.[Na]>C1COCC1>[C:1]([C:3]([NH:6][C:7]([CH:9]([NH:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)=[CH:18][CH:17]=1)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:8])([CH3:5])[CH3:4])#[N:2]

Participants

4

Reactant 2

HCID 18316679N-{1-[(Cyano-dimethyl-methyl)-carbamoyl]-3-methyl-butyl)-4-bromomethyl-benzamideHCID 57373095Imidazole sodium

Product 1

HCID 18316714N-{1-[(Cyano-dimethyl-methyl)-carbamoyl]-3-methyl-butyl}-4-imidazol-1-ylmethyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-{1-[(Cyano-dimethyl-methyl)-carbamoyl]-3-methyl-butyl}-4-bromomethyl-benzamide (0.18 mmol) is dissolved in THF (1 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. An oil with Rf=0.44 (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. customAn oil with Rf=0.44 (CH2Cl2/MeOH=9:1) is obtained

Sources & evidence

ORD record
ord-e34d418ffe5448dda97e389fde424e4c
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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