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

HRID 1466069Notes

Reaction equation

HRID 1466069 reaction equation
[C:1]([C:3]1[C:4]([CH3:27])=[C:5]([C:10](=[O:26])[CH2:11][N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C:13]2=[O:25])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].C(O)(C(F)(F)F)=O>>[F:9][C:8]1[C:3]([C:1]#[N:2])=[C:4]([CH3:27])[C:5]([C:10](=[O:26])[CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][C:13]2=[O:25])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131732684tert-Butyl 4-[2-{3-cyano-4-fluoro-2-methylphenyl}-2-oxoethyl]-3-oxopiperazine-1-carboxylate

Product 1

HCID 895251166-Fluoro-2-methyl-3-[(2-oxopiperazin-1-yl)acetyl]benzonitrile

Procedure

A flask charged with tert-Butyl 4-[2-{3-cyano-4-fluoro-2-methylphenyl}-2-oxoethyl]-3-oxopiperazine-1-carboxylate (0.030 g, 0.08 mmol) was treated with TFA (2.0 mL) for 20 minutes. Analysis of the reaction mixture by LC indicated that reaction had gone to completion. The solution was concentrated in vacuo and crude was co-evaporated with dichloroethane (3×8 mL) to furnish the title product. LC/MS (IE, m/z): [M+1]+=276.

Workup

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

Sources & evidence

ORD record
ord-43f828235cfe40c38c7f29fd5f958b9e
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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