Acetyl chloride → N-[2-(3-{4-cyano-3-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-benzyl}-2-methyl-3H-imidazol-4-yl)-ethyl]-acetamide

HRID 1594864Notes

Reaction equation

HRID 1594864 reaction equation
Cl.Cl.[NH2:3][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]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]4([CH2:36][CH3:37])[CH2:33][CH2:32][CH2:31][CH2:30][N:29]([CH3:34])[C:28]4=[O:35])[CH:22]=3)[CH:13]=2)[C:9]([CH3:38])=[N:8][CH:7]=1.C(N(CC)CC)C.[C:46](Cl)(=[O:48])[CH3:47]>C(Cl)Cl>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([CH2:11][N:10]2[C:6]([CH2:5][CH2:4][NH:3][C:46](=[O:48])[CH3:47])=[CH:7][N:8]=[C:9]2[CH3:38])=[CH:13][C:14]=1[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2([CH2:36][CH3:37])[CH2:33][CH2:32][CH2:31][CH2:30][N:29]([CH3:34])[C:28]2=[O:35])[CH:22]=1)#[N:17]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 217062014-[5-(2-Amino-ethyl)-2-methyl-imidazol-1-ylmethyl]-2-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-benzonitrile dihydrochloride

Product 1

HCID 21706158N-[2-(3-{4-cyano-3-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-benzyl}-2-methyl-3H-imidazol-4-yl)-ethyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[5-(2-amino-ethyl)-2-methyl-imidazol-1-ylmethyl]-2-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-benzonitrile dihydrochloride (as described in Example 11) (0.06 g, 0.108 mmol) in CH2Cl2 (3.0 mL) was added triethylamine (0.06 mL, 0.43 mmol) and acetyl chloride (0.010 mL, 0.14 mmol). After stirring for 2 hr, the solvents were removed in vacuo and the residue was partitioned with EtOAc and saturated NaHCO3. The EtOAc was dried with brine and MgSO4 and evaporated in vacuo to obtain the title compound.

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue was partitioned with EtOAc and saturated NaHCO3
  3. dry with materialThe EtOAc was dried with brine and MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-2be6710153d841aba025b8d0d5f779ba
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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