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 1920959ノート

反応式

HRID 1920959 の反応式
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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a16ab357f2a8440d8118eaa1a5788721
出典データセット
uspto-grants-2012_05
特許番号
US08173657B2

反応ノート

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