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

HRID 1920957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1920957
[CH2:1]([C:5]1[N:6]=[C:7]2[C:16]([N:17](CC3C=CC(OC)=CC=3)CC3C=CC(OC)=CC=3)=[N:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]2[CH:36]=1)[CH:2]([CH3:4])[CH3:3]>FC(F)(F)C(O)=O>[CH2:1]([C:5]1[N:6]=[C:7]2[C:16]([NH2:17])=[N:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]2[CH:36]=1)[CH:2]([CH3:4])[CH3:3]

Komponenten

3

Edukt 1

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

Produkt 1

HCID 167420622-Isobutylimidazo[1,2-a]quinoxalin-4-amineAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

The solution of 2-isobutyl-N,N-bis(4-methoxybenzyl)imidazo[1,2-a]quinoxalin-4-amine (16 mg, 0.033 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 75 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 (6.3 mg, 79%). MS: MH+=241. 1H NMR (300 MHz, CDCl3): δ 7.74 (s, 1H), 7.68 (m, 2H), 7.30-7.40 (m, 4H), 5.70 (brs, 2H), 2.67 (d, 2H), 2.08 (m, 1H), 1.00 (d, 6H).

Aufarbeitung

  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 75 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)

Quellen und Nachweise

ORD-Eintrag
ord-52eb4a2c4ece40e987c906d8f77ac7a0
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173657B2

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