Trifluoroacetic acid → 2-(3,8-Diaza-bicyclo[4.2.0]oct-8-yl)-quinoxaline

HRID 1193056Notes

Reaction equation

HRID 1193056 reaction equation
C(OC([N:8]1[CH2:15][CH2:14][CH:13]2[CH:10]([N:11]([C:16]3[CH:25]=[N:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)[CH2:12]2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>O1CCOCC1>[CH:10]12[N:11]([C:16]3[CH:25]=[N:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)[CH2:12][CH:13]1[CH2:14][CH2:15][NH:8][CH2:9]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 671172578-Quinoxalin-2-yl-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester

Product 1

HCID 671166512-(3,8-Diaza-bicyclo[4.2.0]oct-8-yl)-quinoxalineYield 72%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 8-quinoxalin-2-yl-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester (1.84 g, 5.40 mmol) in dioxane (30 mL) was added trifluoro acetic acid (8.0 mL). The reaction mixture was stirred at rt for 16 h. The solvent and excess trifluoro acetic acid were removed under reduced pressure. The crude product was purified on HPLC (Agilent, basic system) to yield the title compound (925 mg, 72%). MS (ESI) mass calcd. for C14H16N4, 240.3; m/z found, 241.2 [M+H]+. 1H NMR (CDCl3): 1H NMR (400 MHz, CDCl3) 8.12 (s, 1H), 7.86 (dd, J=8.4, 1.0, 1H), 7.67 (dd, J=8.4, 1.0, 1H), 7.54 (dd, J=8.4, 1.5, 1H), 7.37 (dd, J=8.3, 1.4, 1H), 4.45-4.37 (m, 1H), 4.17-4.03 (m, 1H), 3.90-3.82 (m, 1H), 3.57 (dd, J=14.3, 2.0, 1H), 3.19-3.04 (m, 2H), 2.98 (s, 1H), 2.81-2.62 (m, 2H), 2.14-2.03 (m, 1H), 1.85-1.73 (m, 1H).

Workup

  1. customThe solvent and excess trifluoro acetic acid were removed under reduced pressure
  2. customThe crude product was purified on HPLC (Agilent, basic system)

Sources & evidence

ORD record
ord-7602bc1388014bbd9a96aa7b2c19200c
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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