Ammonia → (2S)-2-{2-[4-(3-pyridyl)phthalazin-1(2H)-on-2-yl]isonicotinoylamino}-3-(3,4-dimethoxyphenyl)-1-propanol

HRID 1739433ノート

反応式

HRID 1739433 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][N:24]=1)[C:5]([NH:7][C@@H:8]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)[CH2:9][OH:10])=[O:6].C(=O)([O-])[O-].[K+].[K+].[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40](=[O:47])[NH:39][N:38]=2)[CH:32]=1.N>CN(C)C=O.[Cu]I>[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40](=[O:47])[N:39]([C:2]3[CH:3]=[C:4]([CH:22]=[CH:23][N:24]=3)[C:5]([NH:7][C@@H:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)[CH2:9][OH:10])=[O:6])[N:38]=2)[CH:32]=1

参加物

7

反応物 4

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 100138394-(3-pyridyl)phthalazin-1(2H)-oneHCID 57095136(2S)-2-(2-bromoisonicotinoylamino)-3-(3,4-dimethoxyphenyl)-1-propanol

生成物 1

HCID 18393034(2S)-2-{2-[4-(3-pyridyl)phthalazin-1(2H)-on-2-yl]isonicotinoylamino}-3-(3,4-dimethoxyphenyl)-1-propanol収率 20.2%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To a solution of (2S)-2-(2-bromoisonicotinoylamino)-3-(3,4-dimethoxyphenyl)-1-propanol (1.2 g) in dimethylformamide (40 ml) are added potassium carbonate (0.88 g) and copper (I) iodide (0.61 g) at room temperature under nitrogen atmosphere. The mixture is heated with stirring at 120° C. for 30 minutes. To the reaction mixture is added 4-(3-pyridyl)phthalazin-1(2H)-one (1.42 g), and the mixture is heated with stirring at 130° C. for two hours. The reaction mixture is cooled to room temperature, and thereto is added aqueous ammonia. The mixture is extracted with chloroform, and the extract is washed, dried and concentrated. The residue is purified by silica gel chromatography (solvent; chloroform:acetone=1:1) to give (2S)-2-{2-[4-(3-pyridyl)phthalazin-1(2H)-on-2-yl]isonicotinoylamino}-3-(3,4-dimethoxyphenyl)-1-propanol (330 mg).

後処理

  1. temperatureThe mixture is heated
  2. temperaturethe mixture is heated
  3. stirringwith stirring at 130° C. for two hours
  4. temperatureThe reaction mixture is cooled to room temperature
  5. extractionThe mixture is extracted with chloroform
  6. washthe extract is washed
  7. customdried
  8. concentrationconcentrated
  9. customThe residue is purified by silica gel chromatography (solvent; chloroform:acetone=1:1)

出典と根拠

ORDレコード
ord-803573f5a19c4a8b9c667cbdf9d553b1
出典データセット
uspto-grants-1999_10
特許番号
US05965730

反応ノート

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