Triethylamine → {2-[3-(4-cyano-3-fluoro-benzyl)-2-methyl-3H-imidazol-4-yl]-ethyl}-tert-butyl Urea

HRID 1594894Notes

Reaction equation

HRID 1594894 reaction equation
Cl.Cl.N[CH2:4][CH2:5][C:6]1[N:10]([CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([F:20])[CH:13]=2)[C:9]([CH3:21])=[N:8][CH:7]=1.CC[N:24](CC)CC.[C:29]([N:33]=[C:34]=[O:35])([CH3:32])([CH3:31])[CH3:30]>CN(C=O)C>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([CH2:11][N:10]2[C:6]([CH2:5][CH2:4][N:33]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:34]([NH2:24])=[O:35])=[CH:7][N:8]=[C:9]2[CH3:21])=[CH:13][C:14]=1[F:20])#[N:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 226271114-[5-(2-Amino-ethyl)-2-(methyl)-imidazol-1-ylmethyl]-2-fluoro-benzonitrile dihydrochloride

Product 1

HCID 21706166{2-[3-(4-cyano-3-fluoro-benzyl)-2-methyl-3H-imidazol-4-yl]-ethyl}-tert-butyl Urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[5-(2-amino-ethyl)-2-methyl-imidazol-1-ylmethyl]-2-fluoro-benzonitrile dihydrochloride (as described in Example 34, Step A) (0.3 g, 0.97 mmol) in DMF (5.0 mL) was added NEt3 (0.41 mL, 2.97 mmol) and t-butyl-isocyanate (0.125 mL, 1.07 mmol). After ½ hr the DMF was removed in vacuo and the residue partitioned between EtOAc and saturated NaHCO3. The organic layer was separated, washed with brine and dried (MgSO4). Filtration and concentration in vacuo gave the title compound as an oil.

Workup

  1. customAfter ½ hr the DMF was removed in vacuo
  2. customthe residue partitioned between EtOAc and saturated NaHCO3
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-6de85fadb4b34957932e0455cfd2474d
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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