Water → 2-isobutyl-N,N-bis(4-methoxybenzyl)imidazo[1,2-a]quinoxalin-4-amine

HRID 1920956Notes

Reaction equation

HRID 1920956 reaction equation
Cl[C:2]1[C:3]2[N:4]([CH:12]=[C:13]([CH2:15][CH:16]([CH3:18])[CH3:17])[N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C(N(CC)C(C)C)(C)C.[CH3:28][O:29][C:30]1[CH:46]=[CH:45][C:33]([CH2:34][NH:35][CH2:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)=[CH:32][CH:31]=1.O>CN1CCCC1=O>[CH2:15]([C:13]1[N:14]=[C:3]2[C:2]([N:35]([CH2:34][C:33]3[CH:32]=[CH:31][C:30]([O:29][CH3:28])=[CH:46][CH:45]=3)[CH2:36][C:37]3[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=3)=[N:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]2[CH:12]=1)[CH:16]([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 714952Bis(4-methoxybenzyl)amineHCID 574259094-Chloro-2-isobutylimidazo[1,2-a]quinoxaline

Product 1

HCID 574259102-isobutyl-N,N-bis(4-methoxybenzyl)imidazo[1,2-a]quinoxalin-4-amineYield 81.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of the 4-chloro-2-isobutylimidazo[1,2-a]quinoxaline (130 mg, 0.50 mmol) in 2 mL of 1-methylpyrrolidin-2-one was added N,N-diisopropylethylamine (129 mg, 1.0 mmol) and followed by bis(4-methoxybenzyl)amine (154 mg, 0.60 mmol). The reaction mixture was stirred at 120° C. overnight. And then 10 mL of water was added. The resulting mixture was extracted with ethyl ether (50 mL×3). The combined organic layers were washed with water (20 mL), brine (20 mL), dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography eluted with ethyl acetate and hexanes to give the titled compound (195 mg, 81%). MS: MH+=481 1H NMR (300 MHz, CDCl3): δ 7.72 (s, 1H), 7.65 (m, 2H), 7.21-7.39 (m, 6H), 6.84 (d, 4H), 5.34 (brs, 4H), 3.79 (s, 6H), 2.63 (d, 2H), 2.06 (m, 1H), 0.94 (d, 6H).

Workup

  1. extractionThe resulting mixture was extracted with ethyl ether (50 mL×3)
  2. washThe combined organic layers were washed with water (20 mL), brine (20 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash column chromatography
  7. washeluted with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-948050b34b6d4666828d36cc17dfc26b
Source dataset
uspto-grants-2012_05
Patent number
US08173657B2

Reaction notes

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