Cyclohexylamine → 5-bromo-N-cyclohexylimidazo[1,2-a]pyrazin-8-amine

HRID 1095462

反応式

HRID 1095462 の反応式
[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5](Br)=[N:4][CH:3]=1.[CH:12]1([NH2:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(N(C(C)C)CC)(C)C>C(O)(C)C>[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:18][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:4][CH:3]=1

参加物

5

反応物 3

HCID 7965CyclohexylamineHCID 81531DiisopropylethylamineHCID 534859495,8-Dibromoimidazo[1,2-a]pyrazine

生成物 1

HCID 576994875-bromo-N-cyclohexylimidazo[1,2-a]pyrazin-8-amine収率 69%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
90 °C

実験手順

(5,8-Dibromoimidazo[1,2-a]pyrazine, 200 mg, 0.72 mmol), cyclohexylamine (86 mg, 0.86 mmol) and di-isopropylethylamine (140 mg, 0.74 mmol) are suspended in iso-propanol (5 ml). The mixture is stirred at 90° C. for 18 h. The solvent is evaporated in vacuo and the residue dissolved in dichloromethane (5 mL). The organic layer is washed with saturated NaHCO3(aq) (10 ml), H2O (10 ml) and brine (10 mL). The organic layer is dried (MgSO4) and evaporated in vacuo. The oily residue is purified by column chromatography, eluting with 5:1 hexane:ethyl acetate to give a brown oil (147 mg, 69%). 1H-NMR (400 MHz, d6-DMSO) =1.22-1.29 (m, 1H), 1.32-1.49 (m, 4H), 1.64 (d, 1H, J=15.2 Hz), 1.77 (d, 2H, J=12.8 Hz), 1.92 (d, 2H, J=15.2 Hz), 3.97-4.01 (1H, m), 7.33 (d, 1H, J=8.4 Hz), 7.48 (s, 1H), 7.63 (s, 1H), 7.92 (s, 1H). LCMS: Rt 3.83 min (99.8%), m/z (APCI) 295 (M+H)+.

後処理

  1. customThe solvent is evaporated in vacuo
  2. dissolutionthe residue dissolved in dichloromethane (5 mL)
  3. washThe organic layer is washed with saturated NaHCO3(aq) (10 ml), H2O (10 ml) and brine (10 mL)
  4. dry with materialThe organic layer is dried (MgSO4)
  5. customevaporated in vacuo
  6. customThe oily residue is purified by column chromatography
  7. washeluting with 5:1 hexane

出典と根拠

ORDレコード
ord-23ba4ad7691c45a496cbfe75b1e9d877
出典データセット
uspto-grants-2012_03
特許番号
US08138193B2

関連ノート

読み込み中…