Sodium hydride → Dimethylethyl 5-[5,6-dihydro-5-oxo-pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-6-yl]-alpha-cyano-2-pyridineacetate

HRID 1670696

反応式

HRID 1670696 の反応式
[H-].[Na+].[C:3]([CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])#[N:4].Br[C:14]1[N:19]=[CH:18][C:17]([N:20]2[C:29]3[N:30]4[CH:36]=[CH:35][CH:34]=[CH:33][C:31]4=[N:32][C:28]=3[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]2=[O:37])=[CH:16][CH:15]=1>N1C=CC=CC=1>[O:37]=[C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]2[N:32]=[C:31]3[CH:33]=[CH:34][CH:35]=[CH:36][N:30]3[C:29]=2[N:20]1[C:17]1[CH:16]=[CH:15][C:14]([CH:5]([C:3]#[N:4])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[N:19][CH:18]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 70693tert-Butyl cyanoacetateHCID 247710936-(6-bromo-pyridin-3-yl)-pyrido-[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-one

生成物 1

HCID 57767017Dimethylethyl 5-[5,6-dihydro-5-oxo-pyrido[2',1':2,3]imidazo[4,5-c]isoquinolin-6-yl]-alpha-cyano-2-pyridineacetate収率 45.1%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Sodium hydride (2.2 equiv., 0.844 mmol, 0.034 g (60%)) was added to a solution of tert-butyl cyanoacetate (1.2 equiv., 0.460 mmol, 0.065 g) in dry pyridine (1 ml) under Ar atmosphere. The catalyst—prepared as described above—was injected, and the mixture was stirred at room temperature for 5 min. Compound 21 (1.0 equiv., 0.383 mmol, 0.150 g) was then added and the reaction mixture was heated at 85° C. for 2 h. After destruction of excess sodium hydride with methanol, the solvent was concentrated under vacuum. The residue was purified by column chromatography (dichloromethane/methanol (7M NH3) 95:5) to give dimethylethyl 5-[5,6-dihydro-5-oxo-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-6-yl]-α-cyano-2-pyridineacetate (I12) (0.078 g, yield=45%).

後処理

  1. customThe catalyst—prepared
  2. temperaturethe reaction mixture was heated at 85° C. for 2 h
  3. customAfter destruction of excess sodium hydride with methanol
  4. concentrationthe solvent was concentrated under vacuum
  5. customThe residue was purified by column chromatography (dichloromethane/methanol (7M NH3) 95:5)

出典と根拠

ORDレコード
ord-a2c226f23be34d9798213832d6da0b31
出典データセット
uspto-grants-2011_08
特許番号
US07994187B2

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