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

HRID 1920958Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1920958
[CH2:1]([C:5]1[N:6]=[C:7]2[C:16]([N:17]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=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].C([Li])CCC.[O:42]1[C:44]([CH3:46])([CH3:45])[CH2:43]1>O1CCCC1>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:17]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[C:16]2[C:7]3[N:8]([C:36]([CH2:43][C:44]([CH3:46])([OH:42])[CH3:45])=[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[N:6]=3)[C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:20][CH:21]=1

Komponenten

5

Edukt 3

HCID 11208Isobutylene oxideHCID 574259102-isobutyl-N,N-bis(4-methoxybenzyl)imidazo[1,2-a]quinoxalin-4-amineHCID 178418339Butyllithium

Produkt 1

HCID 580047691-(4-(Bis(4-methoxybenzyl)amino)-2-isobutylimidazo[1,2-a]quinoxalin-1-yl)-2-methylpropan-2-olAusbeute 22,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the 2-isobutyl-N,N-bis(4-methoxybenzyl)imidazo[1,2-a]quinoxalin-4-amine (134 mg, 0.28 mmol) (Example 1, D) in 2 mL of tetrahydrofuran was added n-butyl lithium (2.5M, 0.2 mL, 0.50 mmol) at −78° C. After being stirred at that temperature for 1 hour, 1,2-epoxy-2-methylpropane (72 mg, 1.0 mmol) was added. The reaction mixture was stirred at −78° C. for 2 hours, and then at room temperature for 4 hours. The reaction was quenched with 10 mL of saturated aqueous ammonium chloride. The resulting mixture was extracted with 100 mL of ethyl acetate. The organic layer was separated and 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 (35 mg, 19%) and recovered starting material (100 mg, 63%). MS: MH+=553. 1H NMR (300 MHz, CDCl3): δ 8.41 (dd, 1H), 7.67 (dd, 1H), 7.20-7.37 (m, 6H), 6.84 (m, 4H), 5.31 (brs, 4H), 3.79 (s, 6H), 3.51 (s, 2H), 2.58 (d, 2H), 2.14 (m, 1H), 1.37 (s, 6H), 0.88 (d, 6H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at −78° C. for 2 hours
  2. waitat room temperature for 4 hours
  3. customThe reaction was quenched with 10 mL of saturated aqueous ammonium chloride
  4. extractionThe resulting mixture was extracted with 100 mL of ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water (20 mL), brine (20 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by flash column chromatography
  11. washeluted with ethyl acetate and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-efc1cc4e1eae490eaf898344a7a39023
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173657B2

Notizen zur Reaktion

Wird geladen…