Trifluoroacetic acid → 6-Methoxy-2-methyl-3-[(2-oxopiperazin-1-yl)acetyl]benzonitrile

HRID 1466074Notes

Reaction equation

HRID 1466074 reaction equation
C([C:5]1[CH:12]=[C:11]([O:13][CH3:14])[C:8]([C:9]#[N:10])=[C:7]([CH3:15])[C:6]=1[C:16](=[O:25])[CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][C:19]1=[O:24])(C)(C)C.C(O)(C(F)(F)F)=O>>[CH3:14][O:13][C:11]1[C:8]([C:9]#[N:10])=[C:7]([CH3:15])[C:6]([C:16](=[O:25])[CH2:17][N:18]2[CH2:23][CH2:22][NH:21][CH2:20][C:19]2=[O:24])=[CH:5][CH:12]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131732686tert-Butyl 6-methoxy-2-methyl3-[{2-oxopiperazin-1-yl}acetyl]benzonitrile

Product 1

HCID 895247776-Methoxy-2-methyl-3-[(2-oxopiperazin-1-yl)acetyl]benzonitrile

Procedure

To a flask was added tert-Butyl 6-methoxy-2-methyl3-[{2-oxopiperazin-1-yl}acetyl]benzonitrile (0.060 g, 0.15 mmol) followed by addition of TFA (2 mL) and a stir bar; the resulting mixture was stirred for 20 minutes. Analysis of the reaction mixture by LC indicated that reaction had gone to completion. The solution was concentrated in vacuo and the crude was co-evaporated with dichloroethane (3×8 mL) to furnish the title product. LC/MS (IE, m/z): [M+1]+=288.

Workup

  1. customAnalysis of the reaction mixture by LC indicated that reaction
  2. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-d657b0f8fc8240969c817ecc23ece87b
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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