Trifluoroacetic acid → 2-(2-Oxopiperazin-1-yl)quinoline-6-carbonitrile

HRID 1465734Notes

Reaction equation

HRID 1465734 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([N:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][C:14]1=[O:26])[CH:7]=[CH:6]2)#[N:2].C(O)(C(F)(F)F)=O>>[O:26]=[C:14]1[CH2:15][NH:16][CH2:17][CH2:18][N:13]1[C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:1]#[N:2])[CH:4]=2)[N:9]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131732662tert-Butyl 4-(6-cyanoquinolin-2-yl)-3-oxopiperazine-1-carboxylate

Product 1

HCID 895252942-(2-Oxopiperazin-1-yl)quinoline-6-carbonitrile

Procedure

tert-Butyl 4-(6-cyanoquinolin-2-yl)-3-oxopiperazine-1-carboxylate (0.15 g, 0.79 mmol) was treated with TFA (2 mL) and stirred for 20 minutes. Analysis of the reaction mixture by LC indicated the reaction had gone to completion. The solution was concentrated in vacuo and crude was azetroped (3×) with dichloroethane to furnish the title product. LC/MS (IE, m/z): [M+1]+=253.

Workup

  1. concentrationThe solution was concentrated in vacuo and crude

Sources & evidence

ORD record
ord-afbd1ecaf91047c696c6fecf76fef3d3
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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