Borane-tetrahydrofuran → N-{[1-(2,4-Dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methyl}-N-ethylethanamine

HRID 1628673

反応式

HRID 1628673 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2=[N:15][C:16]3[C:17](=[C:18]([C:22]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=O)[CH:19]=[CH:20][CH:21]=3)[N:13]2[CH2:12][CH2:11][CH2:10]1.[B].O1CCCC1>[Cl-].[NH4+]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2=[N:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[C:17]=3[N:13]2[CH2:12][CH2:11][CH2:10]1

参加物

4

反応物 2

HCID 11062302Borane-tetrahydrofuranHCID 577861461-(2,4-Dichlorophenyl)-N,N-diethyl-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxamide

生成物 1

HCID 57785819N-{[1-(2,4-Dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methyl}-N-ethylethanamine収率 42%

試薬・触媒・溶媒 1

HCID 25517Ammonium Chloride溶媒

反応条件

温度
80 °C

実験手順

To a solution of 1-(2,4-dichlorophenyl)-N,N-diethyl-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxamide (180 mg, 0.431 mmol) was added boron-tetrahydrofuran complex (1.0 M solution in tetrahydrofuran, 2.2 mL, 2.2 mmol), and the mixture was stirred at 80° C. for 3 hr. The mixture was diluted with aqueous saturated ammonium chloride, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate/diisopropyl ether to give the title compound as a colorless crystal (72.2 mg, 0.179 mmol, 42%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture
  7. concentrationThe filtrate was concentrated in vacuo
  8. customto give the solid, which
  9. customwas recrystallized from ethyl acetate/diisopropyl ether

出典と根拠

ORDレコード
ord-148936351dc948ad8761d96f1a30612a
出典データセット
uspto-grants-2014_07
特許番号
US08785460B2

関連ノート

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