N,N'-Dimethylethylenediamine → 2-(4-Chloro-phenyl)-6-[4-(1-methyl-pyrrolidine-3-carbonyl)-phenyl]-6h-thieno[2,3-c]pyridin-7-one, hydrochloride

HRID 2384943노트

반응식

HRID 2384943 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:17][C:11]3[C:12](=[O:16])[NH:13][CH:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.Br[C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH:27]2[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28]2)=[O:26])=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].CNCCNC.Cl.CCOCC>C(Cl)Cl.[Cu]I.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:17][C:11]3[C:12](=[O:16])[N:13]([C:19]4[CH:24]=[CH:23][C:22]([C:25]([CH:27]5[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28]5)=[O:26])=[CH:21][CH:20]=4)[CH:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

참가 물질

9

반응물 5

HCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 10953452Ether hydrochlorideHCID 576495192-(4-Chlorophenyl)-6H,7H-thieno[2,3-c]pyridin-7-oneHCID 68951075HCID 68951075, 화합물

생성물 1

HCID 248037462-(4-Chloro-phenyl)-6-[4-(1-methyl-pyrrolidine-3-carbonyl)-phenyl]-6h-thieno[2,3-c]pyridin-7-one, hydrochloride수율 151.8%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6344Dichloromethane용매2회HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

Combine 2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one (0.15 g, 0.57 mmol), (4-bromo-phenyl)-(1-methyl-pyrrolidin-3-yl)-methanone (0.16 g, 0.60 mmol), Cs2CO3 (0.37 g, 1.15 mmol), 1,4-dioxane (6 mL), and CuI (0.044 g, 0.23 mmol). Purge the mixture with nitrogen for 10 min. Add sym-dimethylethylene diamine (0.040 g, 0.46 mmol). Heat the mixture at 100° C. overnight. Cool the mixture to RT, dilute with CH2Cl2 (200 mL), and wash with a solution of 5% NH4OH/H2O (2×30 mL). Dry the organic layer over Na2SO4, filter, and concentrate. Filter the crude with H2O (200 mL) and Et2O (100 mL). Prepare the HCl salt by dissolving the solid in CH2Cl2 and adding 1 eq 1M HCl/ether. Allow the solution to stir for 15 min and concentrate to give 0.21 g (77%) of the title compound. LC-MS/ES m/z (35Cl) 449.0 [M+H]+.

후처리

  1. customPurge the mixture with nitrogen for 10 min
  2. temperatureCool the mixture to RT
  3. washwash with a solution of 5% NH4OH/H2O (2×30 mL)
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. filtrationFilter the crude with H2O (200 mL) and Et2O (100 mL)
  8. customPrepare the HCl salt
  9. concentrationconcentrate

출처 및 근거

ORD 기록
ord-3ec9ae2f2d854c2fb27b702b4996fa66
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263772B2

반응 노트

불러오는 중…