1-(4-(Bis(4-methoxybenzyl)amino)-2-isobutylimidazo[1,2-a]quinoxalin-1-yl)-2-methylpropan-2-ol → 1-(4-Amino-2-isobutylimidazo[1,2-a]quinoxalin-1-yl)-2-methylpropan-2-ol

HRID 1920959Notes

Reaction equation

HRID 1920959 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[C:10]3[N:11]([C:19]([CH2:26][C:27]([CH3:30])([OH:29])[CH3:28])=[C:20]([CH2:22][CH:23]([CH3:25])[CH3:24])[N:21]=3)[C:12]3[C:17]([N:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=CC=1>FC(F)(F)C(O)=O>[NH2:8][C:9]1[C:10]2[N:11]([C:19]([CH2:26][C:27]([CH3:28])([OH:29])[CH3:30])=[C:20]([CH2:22][CH:23]([CH3:25])[CH3:24])[N:21]=2)[C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

3

Reactant 1

HCID 580047691-(4-(Bis(4-methoxybenzyl)amino)-2-isobutylimidazo[1,2-a]quinoxalin-1-yl)-2-methylpropan-2-ol

Product 1

HCID 249579241-(4-Amino-2-isobutylimidazo[1,2-a]quinoxalin-1-yl)-2-methylpropan-2-olYield 77.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The solution of 1-(4-(bis(4-methoxybenzyl)amino)-2-isobutylimidazo[1,2-a]quinoxalin-1-yl)-2-methylpropan-2-ol (15 mg, 0.027 mmol) in 1 mL of trifluoroacetic acid was stirred at 70° C. for 6 hours. The solvent was removed under reduced pressure. And then 10 mL of saturated aqueous sodium bicarbonate was added. The resulting mixture was extracted with 70 mL of ethyl acetate. The organic layer was separated and then washed with water (15 mL), brine (15 mL), dried over MgSO4, filtered and concentrated. The crude product was purified by preparative TLC sheet (ethyl acetate and hexanes) to give the titled compound (6.5 mg, 77%). MS: MH+=313. 1H NMR (300 MHz, CDCl3): δ 8.41 (dd, 1H), 7.64 (dd, 1H), 7.25-7.41 (m, 2H), 5.63 (brs, 2H), 3.51 (s, 2H), 2.64 (d, 2H), 2.21 (m, 1H), 1.37 (s, 6H), 0.95 (d, 6H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionAnd then 10 mL of saturated aqueous sodium bicarbonate was added
  3. extractionThe resulting mixture was extracted with 70 mL of ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water (15 mL), brine (15 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by preparative TLC sheet (ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-a16ab357f2a8440d8118eaa1a5788721
Source dataset
uspto-grants-2012_05
Patent number
US08173657B2

Reaction notes

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