2-(Methylamino)ethanol → 2-[{3-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]propyl}(methyl)amino]ethanol dihydrochloride

HRID 1787020ノート

反応式

HRID 1787020 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[N:26]([CH2:27][CH2:28][CH2:29]Cl)[CH:25]=[CH:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.[CH3:31][NH:32][CH2:33][CH2:34][OH:35]>CN(C)C=O>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[N:26]([CH2:27][CH2:28][CH2:29][N:32]([CH3:31])[CH2:33][CH2:34][OH:35])[CH:25]=[CH:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

参加物

4

反応物 2

HCID 80162-(Methylamino)ethanolHCID 67520636N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine

生成物 1

HCID 675212082-[{3-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]propyl}(methyl)amino]ethanol dihydrochloride収率 197.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine (634 mg), 2-methylaminoethanol (534 mg) and N,N-dimethylformamide (5 mL) was stirred at room temperature for 64 hrs. After concentration under reduced pressure, saturated aqueous sodium hydrogen carbonate (10 mL) was added to the residue, and the mixture was extracted with ethyl acetate (55 mL×2). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→0:100). 4N Hydrogen chloride-ethyl acetate solution (10 mL) was added to the obtained amorphous solid and, after concentration under reduced pressure, the residue was recrystallized from ethanol-ethyl acetate to give the title compound (523 mg).

後処理

  1. concentrationAfter concentration under reduced pressure, saturated aqueous sodium hydrogen carbonate (10 mL)
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate (55 mL×2)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→0:100)
  7. addition4N Hydrogen chloride-ethyl acetate solution (10 mL) was added to the obtained amorphous solid
  8. concentrationafter concentration under reduced pressure
  9. customthe residue was recrystallized from ethanol-ethyl acetate

出典と根拠

ORDレコード
ord-ae8cc554d3124f4792093edaf161355d
出典データセット
uspto-grants-2009_03
特許番号
US07507740B2

反応ノート

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