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 1970052노트

반응식

HRID 1970052 반응식
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]

참가 물질

6

반응물 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

생성물 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 carboxylate수율 8%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8796feb1ce2d4f999ecb6977cd85b6be
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426437B2

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