1-{3-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridin-8-yl}-ethanone → 2-{3-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridin-8-yl}-propan-2-ol

HRID 226051ノート

反応式

HRID 226051 の反応式
[CH3:1][Mg+].[Br-].[CH2:4]([CH:6]([C:9]1[C:10]2[N:11]([C:16]([C:20]3[N:24]4[CH:25]=[CH:26][CH:27]=[C:28]([C:29](=[O:31])[CH3:30])[C:23]4=[N:22][C:21]=3[CH3:32])=[C:17]([CH3:19])[N:18]=2)[N:12]=[C:13]([CH3:15])[CH:14]=1)[CH2:7][CH3:8])[CH3:5]>C1COCC1>[CH2:4]([CH:6]([C:9]1[C:10]2[N:11]([C:16]([C:20]3[N:24]4[CH:25]=[CH:26][CH:27]=[C:28]([C:29]([OH:31])([CH3:1])[CH3:30])[C:23]4=[N:22][C:21]=3[CH3:32])=[C:17]([CH3:19])[N:18]=2)[N:12]=[C:13]([CH3:15])[CH:14]=1)[CH2:7][CH3:8])[CH3:5]

参加物

4

反応物 2

HCID 577526751-{3-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridin-8-yl}-ethanoneHCID 178418689HCID 178418689、化合物

生成物 1

HCID 577526202-{3-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridin-8-yl}-propan-2-ol収率 61%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A suspension of CeCl3 (0.37 g, 2.22 mmol) in THF (10 mL) is stirred at RT for 2 h. It is then cooled to 0° C., and treated with 3.0 M CH3MgBr (0.74 mL, 2.22 mmol). The mixture is stirred at 0° C. for 2 h. A solution of 1-{3-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-2-methyl-imidazo[1,2-a]pyridin-8-yl}-ethanone (0.57 g, 1.48 mmol) in THF (5 mL) is added to the mixture at 0° C. The reaction is stirred at 0° C. for 30 min and at RT for 2 h. It is finally quenched with sat. NH4Cl (10 mL), diluted with H2O (50 mL); extracted with EtOAc (3×100 mL). The combined organic layers is dried with Na2SO4, filtered and concentrated. Purification of the crude material by silica gel chromatography gives the title compound (0.36 g, 0.90 mmol, 61%). 1H NMR (CDCl3): δ 0.92 (t, J=7.5 Hz, 3H), 0.93 (t, J=7.5 Hz, 3H), 1.80 (s, 6H), 1.80-1.95 (m, 4H), 2.41 (s, 3H), 2.42 (s, 3H), 2.45 (s, 3H), 3.31-3.41 (m, 1H), 6.67-6.74 (m, 1H), 6.73 (s, 1H), 6.92 (bs, 1H), 7.09 (bs, 1H), 7.41 (d, J=5.6 Hz, 1H) ppm. ES-MS (m/z): calcd for C24H31N5O (M+H)+: 406.6. found: 406.3.

後処理

  1. temperatureIt is then cooled to 0° C.
  2. stirringThe mixture is stirred at 0° C. for 2 h
  3. stirringThe reaction is stirred at 0° C. for 30 min and at RT for 2 h
  4. customIt is finally quenched with sat. NH4Cl (10 mL)
  5. additiondiluted with H2O (50 mL)
  6. extractionextracted with EtOAc (3×100 mL)
  7. dry with materialThe combined organic layers is dried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification of the crude material by silica gel chromatography

出典と根拠

ORDレコード
ord-f9f09b57bf304cc4be560fa77b291d8e
出典データセット
uspto-grants-2009_07
特許番号
US07557103B2

反応ノート

読み込み中…