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1,1'-Carbonyldiimidazole → 6-(2,4-Dichloro-phenyl)-5-(2-methoxy-ethoxy)-pyrazine-2-carboxylic acid (2-cyclopropyl-2-hydroxy-propyl)-amide

HRID 1865888
ノート
印刷プレビュー

反応式

HRID 1865888 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]([OH:17])=O)[CH:12]=[N:11][C:10]=1[O:18][CH2:19][CH2:20][O:21][CH3:22].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:35][CH2:36][C:37]([CH:40]1[CH2:42][CH2:41]1)([OH:39])[CH3:38]>CN(C)C=O>[CH:40]1([C:37]([OH:39])([CH3:38])[CH2:36][NH:35][C:15]([C:13]2[CH:12]=[N:11][C:10]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[N:14]=2)=[O:17])[CH2:42][CH2:41]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 211096921-Amino-2-cyclopropylpropan-2-olHCID 688010876-(2,4-Dichloro-phenyl)-5-(2-methoxy-ethoxy)-pyrazine-2-carboxylic acid

生成物 1

HCID 866169736-(2,4-Dichloro-phenyl)-5-(2-methoxy-ethoxy)-pyrazine-2-carboxylic acid (2-cyclopropyl-2-hydroxy-propyl)-amide収率 5.3%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

To a solution of 0.030 g (0.0009 mol) of 6-(2,4-dichloro-phenyl)-5-(2-methoxy-ethoxy)-pyrazine-2-carboxylic acid in 2.0 ml dimethylformamide was added at room temperature 0.029 g (0.0018 mol) of 1,1′-carbonyldiimidazole and the mixture was stirred at room temperature for 1 hour. To the resulting brown solution was added 0.020 g (0.0018 mol) 1-amino-2-cyclopropyl-propan-2-ol and the mixture was stirred for 3 hours. The reaction mixture was then partitioned between 10% aqueous citric acid and ethyl acetate. The phases were separated and the organic layer washed with 10% aqueous sodium bicarbonate and brine dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel using a gradient of heptane to ethyl acetate to yield 0.021 g of the title compound as colorless oil. MS (ISP) (M+H+)=440.4.

後処理

  1. stirringthe mixture was stirred for 3 hours
  2. customThe reaction mixture was then partitioned between 10% aqueous citric acid and ethyl acetate
  3. customThe phases were separated
  4. washthe organic layer washed with 10% aqueous sodium bicarbonate and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel using a gradient of heptane to ethyl acetate

出典と根拠

ORDレコード
ord-67ec9feb8255448386c03359604435de
出典データセット
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07629346B2

反応ノート

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