Water → 5-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyrazine-2-carboxylic acid isopropylamide

HRID 600483ノート

反応式

HRID 600483 の反応式
[CH:1]([NH2:4])([CH3:3])[CH3:2].C[Al](C)C.C[O:10][C:11]([C:13]1[CH:18]=[N:17][C:16]([NH:19][CH2:20][C:21]2[C:22]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:23][O:24][C:25]=2[CH3:26])=[CH:15][N:14]=1)=O.O>O1CCOCC1>[CH:1]([NH:4][C:11]([C:13]1[CH:18]=[N:17][C:16]([NH:19][CH2:20][C:21]2[C:22]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:23][O:24][C:25]=2[CH3:26])=[CH:15][N:14]=1)=[O:10])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 684456305-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyrazine-2-carboxylic acid methyl ester

生成物 1

HCID 426358785-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyrazine-2-carboxylic acid isopropylamide収率 85.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

To a solution of isopropylamine (0.69 mL, 8 mmol) in dioxane (5 mL) was added dropwise trimethylaluminum solution (2M solution in hexane, 4 mL, 8 mmol). After stirring for 1 h at room temperature a suspension of 5-[(5-methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyrazine-2-carboxylic acid methyl ester (650 mg, 2 mmol) in dioxane (5 mL) was added. The reaction mixture was stirred at 90° C. for 90 min, cooled to room temperature and poured into water. Extraction with ethyl acetate and washing with saturated aqueous Seignette salt solution was followed by drying of the organic phase over sodium sulfate and evaporation which afforded an oil. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 20:80) afforded the title compound (600 mg, 85%) as a white solid MS: m/e=352.3 [M+H]+.

後処理

  1. additionwas added
  2. stirringThe reaction mixture was stirred at 90° C. for 90 min
  3. temperaturecooled to room temperature
  4. extractionExtraction with ethyl acetate
  5. washwashing with saturated aqueous Seignette salt solution
  6. dry with materialby drying of the organic phase over sodium sulfate and evaporation which
  7. customafforded an oil
  8. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 20:80)

出典と根拠

ORDレコード
ord-e3699bbf3d88467abc4a0835a2550311
出典データセット
uspto-grants-2011_03
特許番号
US07902201B2

反応ノート

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