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Dimethylformamide → 2,2-dimethyl-N-[5-[6-(4-methyl-1-piperidyl)imidazo[2,1-f]pyridazin-2-yl]-2-(trifluoromethyl)phenyl]propanamide

HRID 539751
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HRID 539751 반응식
CN(C=O)C.[CH3:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:20]1[CH:25]=[CH:24][C:23]2=[N:26][C:27]([C:29]3[CH:30]=[CH:31][C:32]([C:42]([F:45])([F:44])[F:43])=[C:33]([NH:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])[CH:34]=3)=[CH:28][N:22]2[N:21]=1>O>[CH3:38][C:37]([CH3:40])([CH3:39])[C:36]([NH:35][C:33]1[CH:34]=[C:29]([C:27]2[N:26]=[C:23]3[N:22]([CH:28]=2)[N:21]=[C:20]([N:10]2[CH2:11][CH2:12][CH:7]([CH3:6])[CH2:8][CH2:9]2)[CH:25]=[CH:24]3)[CH:30]=[CH:31][C:32]=1[C:42]([F:44])([F:43])[F:45])=[O:41]
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6

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HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 693814-MethylpiperidineHCID 86667850N-(5-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-(trifluoromethyl)phenyl)pivalamide

생성물 1

HCID 679828202,2-dimethyl-N-[5-[6-(4-methyl-1-piperidyl)imidazo[2,1-f]pyridazin-2-yl]-2-(trifluoromethyl)phenyl]propanamide수율 43.5%

시약·촉매·용매

1
HCID 962Water용매

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온도
120 °C

실험 절차

An 8 mL vial is charged with DMF (1 mL), 4-methylpiperidine (0.030 g), Cs2CO3 (0.130 g), and N-[5-(6-chloroimidazo[2,1-f]pyridazin-2-yl)-2-(trifluoromethyl)phenyl]-2,2-dimethyl-propanamide (0.0396 g, 0.1 mmol). The mixture is stirred at 120° C. for 16 hr, then diluted with H2O (5 mL) and extracted with Et2O (3 mL×2). Organics are dried and concentrated onto celite, purified by silica gel chromatography (0-100% EtOAc in Hexanes) to give the title compound (0.020 g, 43% yield). LCMS m/z=460.6 [M+H]+, tR=3.14 min. (compound same as Example 233)

후처리

  1. extractionextracted with Et2O (3 mL×2)
  2. customOrganics are dried
  3. concentrationconcentrated onto celite
  4. custompurified by silica gel chromatography (0-100% EtOAc in Hexanes)

출처 및 근거

ORD 기록
ord-fbce0e91417a49079c8c1f745a35a0b2
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08871767B2

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