Formaldehyde → 8-{3-[(2-cyano-ethyl)-methyl-amino]-prop-1-ynyl}-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1970052ノート

反応式

HRID 1970052 の反応式
C=O.[CH3:3][N:4]([CH2:9][C:10]#[CH:11])[CH2:5][CH2:6][C:7]#[N:8].C([C:14]1[CH:23]=[CH:22][C:21]2[NH:20][C:19](=[O:24])[C:18]3[NH:25][CH:26]=[CH:27][C:17]=3[C:16]=2[CH:15]=1)#C.[CH2:28]([C:30]([O-:32])=[O:31])[CH3:29]>O1CCOCC1.[Cu](I)I>[C:7]([CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][C:10]#[C:11][C:14]1[CH:23]=[CH:22][C:21]2[NH:20][C:19](=[O:24])[C:18]3[NH:25][CH:26]=[CH:27][C:17]=3[C:16]=2[CH:15]=1)#[N:8].[CH2:28]([C:30]([O-:32])=[O:31])[CH3:29]

参加物

6

反応物 3

HCID 712FormaldehydeHCID 160390963-(Methyl-prop-2-ynyl-amino)-propionitrileHCID 866275508-ethynyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

生成物 1

HCID 866275588-{3-[(2-cyano-ethyl)-methyl-amino]-prop-1-ynyl}-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate収率 8%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

31 mg (0.35 mmol) of para-formaldehyde, 35 mg (0.42 mmol) of 3-(methyl-prop-2-ynyl-amino)-propionitrile and 7 mg (0.04 mmol) of copper iodide are added to a suspension of 98 mg (0.35 mmol) of 8-ethynyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 3 ml of anhydrous dioxan, then the mixture is heated at 110° C. for 6 hours. The raw reaction product is then filtered, and the filtrate is evaporated. The residue is triturated with methanol, then the new filtrate is evaporated. The product is recrystallized from methanol to give 10 mg (8%) of 8-{3-[(2-cyano-ethyl)-methyl-amino]-prop-1-ynyl}-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

後処理

  1. customThe raw reaction product
  2. filtrationis then filtered
  3. customthe filtrate is evaporated
  4. customThe residue is triturated with methanol
  5. customthe new filtrate is evaporated
  6. customThe product is recrystallized from methanol

出典と根拠

ORDレコード
ord-8796feb1ce2d4f999ecb6977cd85b6be
出典データセット
uspto-grants-2013_04
特許番号
US08426437B2

反応ノート

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