Ethyl Acetate → 4-(2-{Butyl-[4-(4-methoxy-phenyl)-thiazol-2-yl]-amino}-ethyl)-benzonitrile

HRID 1441697Notes

Reaction equation

HRID 1441697 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH:14][CH2:15][CH2:16][C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[S:12][CH:13]=2)=[CH:5][CH:4]=1.[H-].[Na+].I[CH2:28][CH2:29][CH2:30][CH3:31].C(OCC)(=O)C>CN(C)C=O>[CH2:28]([N:14]([C:11]1[S:12][CH:13]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[N:10]=1)[CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=1)[CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 591646184-{2-[4-(4-Methoxy-phenyl)-thiazol-2-ylamino]-ethyl}-benzonitrile

Product 1

HCID 598060244-(2-{Butyl-[4-(4-methoxy-phenyl)-thiazol-2-yl]-amino}-ethyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

600 mg 4-{2-[4-(4-Methoxy-phenyl)-thiazol-2-ylamino]-ethyl}-benzonitrile were dissolved in 30 ml dimethylformamide. 85.9 mg sodium hydride (24% in mineral oil) were added and the reaction mixture stirred at room temperature for thirty minutes. Then 245 μl 1-Iodobutane were added and the reaction mixture stirred at room temperature for two hours. Then 100 ml ethyl acetate were added and the mixture was washed three times with portions of 50 ml water and then dried over MgSO4. The solvents were removed in vacuo and the residue purified by RP-HPLC to obtain 279 mg 4-(2-{Butyl-[4-(4-methoxy-phenyl)-thiazol-2-yl]-amino}-ethyl)-benzonitrile.

Workup

  1. stirringthe reaction mixture stirred at room temperature for two hours
  2. washthe mixture was washed three times with portions of 50 ml water
  3. dry with materialdried over MgSO4
  4. customThe solvents were removed in vacuo
  5. customthe residue purified by RP-HPLC

Sources & evidence

ORD record
ord-1e731c8752ee41d88bf5f7d3ef85ce71
Source dataset
uspto-grants-2010_02
Patent number
US07655679B2

Reaction notes

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