Ethyl Acetate → 4-[2-(Benzooxazol-2-yl-butyl-amino)-ethyl]-benzonitrile

HRID 1441688Notes

Reaction equation

HRID 1441688 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH3:4].Cl[C:17]1[O:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>CN(C)C=O>[O:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 119862-ChlorobenzoxazoleHCID 81531DiisopropylethylamineHCID 591645764-(2-Butylamino-ethyl)-benzonitrile

Product 1

HCID 591645944-[2-(Benzooxazol-2-yl-butyl-amino)-ethyl]-benzonitrileYield 24.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 750 mg 4-(2-Butylamino-ethyl)-benzonitrile, 854 mg 2-chlorobenzooxazole and 0.95 ml N,N-diisopropylethylamine in 10 ml dimethylformamide were stirred under microwave irradiation at 200° C. for thirty minutes. The cooled reaction mixture was diluted by the addition of 60 ml ethyl acetate, then washed three times with 40 ml brine. The organic layer was dried over MgSO4, then the solvent was removed in vacuo. The residue was purified by RP-HPLC to obtain 290 mg 4-[2-(Benzooxazol-2-yl-butyl-amino)-ethyl]-benzonitrile as pale yellow amorphous solid.

Workup

  1. customThe cooled reaction mixture
  2. washwashed three times with 40 ml brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-b7a9b2d938044a46947bc8a8b6cec4d4
Source dataset
uspto-grants-2010_02
Patent number
US07655679B2

Reaction notes

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