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Butyric Acid → 4-((4-Fluorobenzyl)oxy)-1-(1-methyl-2-propyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2202900
ノート
印刷プレビュー

反応式

HRID 2202900 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[CH:10][C:9]2=[O:23])=[CH:4][C:3]=1[NH:24][CH3:25].CN(C(ON1N=N[C:36]2[CH:37]=CC=N[C:35]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:50](O)(=O)CCC.C(N(CC)C(C)C)(C)C.[Cl-].[Cl-].[Ca+2]>CN(C=O)C>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][O:14][C:11]2[CH:12]=[CH:13][N:8]([C:5]3[CH:6]=[CH:7][C:2]4[N:1]=[C:25]([CH2:35][CH2:36][CH3:37])[N:24]([CH3:50])[C:3]=4[CH:4]=3)[C:9](=[O:23])[CH:10]=2)=[CH:17][CH:18]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 264Butyric AcidHCID 81531DiisopropylethylamineHCID 5284359Calcium ChlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 896902791-(4-Amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one

生成物 1

HCID 89691535
4-((4-Fluorobenzyl)oxy)-1-(1-methyl-2-propyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 1-(4-amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (90 mg), HATU (106 mg), n-butyric acid (0.024 ml), N,N-diisopropylethylamine (0.136 ml) and DMF (2 ml) was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was dissolved in AcOH (2.0 ml) and stirred at 90° C. for 1 h. After evaporation, the residue was purified by NH silica gel column chromatography (hexane/EtOAc). The resulting solid was recrystallized from EtOAc/MeOH to give the title compound (48.7 mg) as an off-white solid.

後処理

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. dissolutionThe resulting residue was dissolved in AcOH (2.0 ml)
  8. customAfter evaporation
  9. customthe residue was purified by NH silica gel column chromatography (hexane/EtOAc)
  10. customThe resulting solid was recrystallized from EtOAc/MeOH

出典と根拠

ORDレコード
ord-36249f2799a049f4b3c3cf3a3ebed522
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09365540B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート