Trifluoroacetic acid → 1-[2-(1,3-Dihydro-1-oxo-5-isobenzofuranyl)ethyl]-2-piperazinone

HRID 1466060Notes

Reaction equation

HRID 1466060 reaction equation
C(OC(=O)[CH2:5][NH:6][CH2:7][CH2:8][N:9]([C:22]([O:24]C(C)(C)C)=O)[CH2:10][CH2:11][C:12]1[CH:21]=[CH:20][C:15]2[C:16](=[O:19])[O:17][CH2:18][C:14]=2[CH:13]=1)C.C(O)(C(F)(F)F)=O.CCN(C(C)C)C(C)C>>[O:19]=[C:16]1[C:15]2[CH:20]=[CH:21][C:12]([CH2:11][CH2:10][N:9]3[CH2:8][CH2:7][NH:6][CH2:5][C:22]3=[O:24])=[CH:13][C:14]=2[CH2:18][O:17]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 131732682Ethyl[(2-{(tert-butoxycarbonyl)[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]amino}ethyl)amino]acetate

Product 1

HCID 1175993331-[2-(1,3-Dihydro-1-oxo-5-isobenzofuranyl)ethyl]-2-piperazinone

Procedure

To a flask charged with Ethyl[(2-{(tert-butoxycarbonyl)[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]amino}ethyl)amino]acetate (280 mg, 0.69 mmol) and a stir bar was added TFA (2 mL). The mixture was allowed to stir at RT for 1 hour. The solvent was removed under vacuum, and the residue was dissolved in EtOH (5 mL). To the solution was added Hunig's base (0.36 mL, 2.1 mmol), and the solution was heated to 150° C. in a microwave tube for 45 minutes. LC showed mostly product, which was purified by silica gel chromatography (MeOH-DCM). The adduct was treated with 4N HCl to remove the BOC group and provide the title compound. LC-MS (IE, m/z): 261 [M+1]+.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in EtOH (5 mL)
  3. temperaturethe solution was heated to 150° C. in a microwave tube for 45 minutes
  4. customwas purified by silica gel chromatography (MeOH-DCM)
  5. additionThe adduct was treated with 4N HCl
  6. customto remove the BOC group

Sources & evidence

ORD record
ord-cc9f5145dee04715bbb5d51458106f91
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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