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Iodoethane → 5-[9-Chloro-6-(1-ethoxypropyl)-3,4-dihydropyrimido[1,2-a]benzimidazol-1(2H)-yl]-N,N,4-trimethylpyridin-2-amine

HRID 1628731
ノート
印刷プレビュー

反応式

HRID 1628731 の反応式
[H-].[Na+].[Cl:3][C:4]1[C:12]2[N:11]=[C:10]3[N:13]([C:17]4[CH:18]=[N:19][C:20]([N:24]([CH3:26])[CH3:25])=[CH:21][C:22]=4[CH3:23])[CH2:14][CH2:15][CH2:16][N:9]3[C:8]=2[C:7]([CH:27]([OH:30])[CH2:28][CH3:29])=[CH:6][CH:5]=1.[CH2:31](I)[CH3:32]>CN(C)C=O.[Cl-].[NH4+]>[Cl:3][C:4]1[C:12]2[N:11]=[C:10]3[N:13]([C:17]4[C:22]([CH3:23])=[CH:21][C:20]([N:24]([CH3:25])[CH3:26])=[N:19][CH:18]=4)[CH2:14][CH2:15][CH2:16][N:9]3[C:8]=2[C:7]([CH:27]([O:30][CH2:31][CH3:32])[CH2:28][CH3:29])=[CH:6][CH:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 577861671-{9-Chloro-1-[6-(dimethylamino)-4-methylpyridin-3-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl}propan-1-ol

生成物 1

HCID 577860355-[9-Chloro-6-(1-ethoxypropyl)-3,4-dihydropyrimido[1,2-a]benzimidazol-1(2H)-yl]-N,N,4-trimethylpyridin-2-amine収率 50.1%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 25517Ammonium Chloride溶媒

実験手順

Sodium hydride (60% in oil, 27.1 mg, 0.678 mmol) was added to a stirred solution of 1-{9-chloro-1-[6-(dimethylamino)-4-methylpyridin-3-yl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl}propan-1-ol (226 mg, 0.565 mmol) in N,N-dimethylformamide (5.0 mL) at room temperature. After stirring 5 min, ethyl iodide (132 mg, 0.848 mmol) was added to the mixture, and the mixture was stirred at room temperature for 6 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 50-100% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate to give the title compound as a colorless crystal (121 mg, 0.283 mmol, 50%).

後処理

  1. stirringthe mixture was stirred at room temperature for 6 hr
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto give the solid, which
  10. customwas recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-726a1590b6a74a9488dceb9d0e22776f
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785460B2

反応ノート

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