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

HRID 1093959

반응식

HRID 1093959 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 576994875-bromo-N-cyclohexylimidazo[1,2-a]pyrazin-8-amine수율 69.2%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
90 °C

실험 절차

Intermediate 2 (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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-3862a0fe5efe45a5913d9c1229af7dc2
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133895B2

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