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4-Methylmorpholine → N-[5-(6-cyanoimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide

HRID 539753
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HRID 539753 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:24]([F:27])([F:26])[F:25])=[C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=3)=[CH:10][N:4]2[N:3]=1.[Cu](C#N)[C:29]#[N:30].CN1CCOCC1>CCOCC.C([O-])(O)=O.[Na+]>[C:29]([C:2]1[CH:7]=[CH:6][C:5]2=[N:8][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:24]([F:27])([F:26])[F:25])=[C:15]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=3)=[CH:10][N:4]2[N:3]=1)#[N:30]
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6

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HCID 79724-MethylmorpholineHCID 86667850N-(5-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-(trifluoromethyl)phenyl)pivalamideHCID 178418260HCID 178418260, 화합물

생성물 1

HCID 67983247N-[5-(6-cyanoimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide수율 26%

시약·촉매·용매 2

HCID 3283Diethyl Ether
용매
HCID 516892Sodium Bicarbonate용매

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온도
215 °C

실험 절차

An 8 mL vial is charged with N-[5-(6-chloroimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide (0.059 g, 0.15 mmol), copper cyanide (0.035 g, 0.3 mmol), and 4-methylmorpholine (0.43 mL). The mixture is stirred at 215° C. for 4 hr in the microwave, then cooled, diluted with Et2O, sat. aqueous NaHCO3 and the biphasic mixture is filtered. Organics are collected and aqueous layer is extracted twice more with Et2O. Organics are combined, dried, concentrated, and purified by prep plate TLC (1:1 Hex:EtOAc) to give the title compound (15 mg, 26% yield). LCMS m/z=388.5 [M+H]+, tR=2.56 min. (compound same as Example 173)

후처리

  1. temperaturecooled
  2. filtrationthe biphasic mixture is filtered
  3. customOrganics are collected
  4. extractionaqueous layer is extracted twice more with Et2O
  5. customdried
  6. concentrationconcentrated
  7. custompurified by prep plate TLC (1:1 Hex:EtOAc)

출처 및 근거

ORD 기록
ord-012bf39a62ff45a6969a4a1757144da0
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08871767B2

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