Sodium Bicarbonate → N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5-[3-(dimethylamino)propyl]-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride

HRID 1926108ノート

反応式

HRID 1926108 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.C(=O)([O-])O.[Na+].[CH3:36][NH:37][CH3:38].O1CCCC1>>[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:37]([CH3:38])[CH3:36])[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 3

HCID 516892Sodium BicarbonateHCID 22320367Dimethylamine tetrahydrofuran3 回HCID 67520636N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine

生成物 1

HCID 67520425N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5-[3-(dimethylamino)propyl]-5H-pyrrolo[3,2-d]pyrimidin-4-amine dihydrochloride

実験手順

N-{3-Chloro-4-[(3-fluorobenzyl)oxy]phenyl}-5-(3-chloropropyl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine (560 mg) was dissolved in 2.0 M dimethylamine-tetrahydrofuran solution (5 mL), and the mixture was stirred at room temperature for 26 hrs. A 2.0 M dimethylamine-tetrahydrofuran solution (5 mL) was further added and the mixture was stirred at room temperature for 20 hrs. A 2.0 M dimethylamine-tetrahydrofuran solution (10 mL) was further added, and the mixture was stirred at room temperature for 24 hrs. After concentration of the reaction mixture under reduced pressure, saturated aqueous sodium hydrogen carbonate (20 mL) was added to the residue, and the mixture was extracted with ethyl acetate (35 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=90:10→20:80), and 4N hydrogen chloride-ethyl acetate solution (10 mL) was added to the obtained amorphous solid. After concentration under reduced pressure, the residue was recrystallized from ethanol-ethyl acetate to give the title compound (428 mg).

後処理

  1. stirringthe mixture was stirred at room temperature for 20 hrs
  2. stirringthe mixture was stirred at room temperature for 24 hrs
  3. extractionthe mixture was extracted with ethyl acetate (35 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=90:10→20:80), and 4N hydrogen chloride-ethyl acetate solution (10 mL)
  7. additionwas 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-753a814584074774831ab950f1b047f5
出典データセット
uspto-grants-2012_05
特許番号
US08178543B2

反応ノート

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