Trifluoroacetic acid → 7-Methyl-2-(2-oxopiperazin-1-yl)quinoline-6-carbonitrile

HRID 1465738Notes

Reaction equation

HRID 1465738 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[N:9]=[C:8]([N:14]1[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][C:15]1=[O:27])[CH:7]=[CH:6]2)#[N:2].C(O)(C(F)(F)F)=O>>[CH3:13][C:12]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][C:15]3=[O:27])=[N:9]2)=[CH:4][C:3]=1[C:1]#[N:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131732663tert-Butyl 4-(6-cyano-7-methylquinolin-2-yl)-3-oxopiperazine-1-carboxylate

Product 1

HCID 895251837-Methyl-2-(2-oxopiperazin-1-yl)quinoline-6-carbonitrile

Procedure

tert-Butyl 4-(6-cyano-7-methylquinolin-2-yl)-3-oxopiperazine-1-carboxylate was treated with TFA (2 mL) and 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 crude was azetroped (3×) with dichloroethane to furnish the title compound. LC/MS (IE, m/z): [M+1]+=267.

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-2404efb97ec74c27abd74cf76fa80da3
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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