HCID 70095412, compound → HCID 178419990, compound

HRID 868915Notes

Reaction equation

HRID 868915 reaction equation
[NH2:1][C:2]1[C:11]([NH:12][C:13](=O)[CH2:14][CH2:15][C:16]2[CH:25]=[N:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.NC1C(NC(=O)CCC2C=NC3C(=CC=CC=3)N=2)=C2C(=CC=1)N=CC=C2>C(O)(=O)C>[N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:24]=[CH:25][C:16]=1[CH2:15][CH2:14][C:13]1[NH:1][C:2]2=[C:3]3[C:8](=[CH:9][CH:10]=[C:11]2[N:12]=1)[N:7]=[CH:6][CH:5]=[CH:4]3

Participants

4

Reactant 2

HCID 70095412HCID 70095412, compoundHCID 70097400HCID 70097400, compound

Product 1

HCID 178419990HCID 178419990, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-(5-Aminoquinolin-6-yl)-3-(quinoxalin-2-yl)propanamide (180 mg, 0.5 mmol) or N-(6-aminoquinolin-5-yl)-3-(quinoxalin-2-yl)propanamide (80 mg, 0.23 mmol) in acetic acid (5 mL or 2 mL, respectively) was heated to 60° C. and stirred for 2 hours. Excess acetic acid was removed under vacuum, and the residue was purified by column chromatography to afford 2-(2-(quinoxalin-2-yl)ethyl)-3H-imidazo[4,5-f]quinoline (150 mg) and 2-(2-(quinoxalin-2-yl)ethyl)-1H-imidazo[4,5-f]quinoline (60 mg). MS (ESI) m/z 325 (M+H+).

Workup

  1. customExcess acetic acid was removed under vacuum
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0ef52d4b75294a33be15dfcea1357e5a
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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