Water → 3-[Bis(4-methoxybenzyl)amino]-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbonitrile

HRID 915041노트

반응식

HRID 915041 반응식
[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[N:16]=[C:15]([C:17]#[N:18])[C:14]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[N:13][C:12]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:5]1)([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=1.O>CC(N(C)C)=O>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:19]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[C:14]2[C:15]([C:17]#[N:18])=[N:16][C:11]([C:6]3[CH:7]=[CH:8][C:9](=[O:10])[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=3)=[C:12]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:13]=2)=[CH:26][CH:25]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 693318746-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-[(4-methoxybenzyl)amino]-5-phenyl-2-pyrazinecarbonitrile

생성물 1

HCID 693319503-[Bis(4-methoxybenzyl)amino]-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbonitrile

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
22.5 °C

실험 절차

6-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-3-[(4-methoxybenzyl)amino]-5-phenyl-2-pyrazinecarbonitrile (14.61 g) was added to a suspension of NaH (60% in oil suspension) (1.36 g) in DMA (36.5 ml) and the mixture was stirred at 20-25° C. for an hour. After addition of 1-(chloromethyl)-4-methoxybenzene (4.82 ml), the mixture was stirred at the same temperature for 20 hours. To the reaction mixture was added water (183 ml) and a precipitate was collected by filtration. The precipitate was purified by column chromatography on silica gel (EtOAc only) to give a solid. The solid was crystallized from a mixture of n-hexane and CHCl3 to give 3-[bis(4-methoxybenzyl)amino]-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-5-phenyl-2-pyrazinecarbonitrile (16.58 g).

후처리

  1. stirringthe mixture was stirred at the same temperature for 20 hours
  2. filtrationa precipitate was collected by filtration
  3. customThe precipitate was purified by column chromatography on silica gel (EtOAc only)
  4. customto give a solid
  5. customThe solid was crystallized from a mixture of n-hexane and CHCl3

출처 및 근거

ORD 기록
ord-50d12557b217420f95f60f4dd7f738cf
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265120B2

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