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

반응식

HRID 1670696 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-a2c226f23be34d9798213832d6da0b31
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994187B2

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