Tetrahydrofuran → N'-[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(pyridin-3-ylcarbonyl)furo[2,3-b]pyridin-3-yl]-N,N-dimethylurea

HRID 8791

반응식

HRID 8791 반응식
[H-].[Na+].[NH2:3][C:4]1[C:12]2[C:7](=[N:8][C:9]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[CH:11]=2)[O:6][C:5]=1[C:28]([C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)=[O:29].[CH3:36][N:37]([CH3:42])S(Cl)(=O)=O.C1[CH2:47][O:46]CC1>>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[CH:11]=[C:12]3[C:4]([NH:3][C:47](=[O:46])[N:37]([CH3:42])[CH3:36])=[C:5]([C:28]([C:30]4[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=4)=[O:29])[O:6][C:7]3=[N:8][C:9]=2[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[Cl:27])=[CH:18][CH:17]=1

참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran2회HCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 9983227[3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl](pyridin-3-yl)methanone

생성물 1

HCID 10437904N'-[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(pyridin-3-ylcarbonyl)furo[2,3-b]pyridin-3-yl]-N,N-dimethylurea

반응 조건

온도
0 °C

실험 절차

To a suspension of sodium hydride (0.004 g; 60% dispersion; 0.111 mmol) in THF (0.5 mL) at 0° C. was added a solution of 0.050 g 0.101 mmol) of the product from Example 26 (in THF (0.5 mL) and the reaction mixture was stirred at 0° C. for 30 minutes. Dimethylsulfamoyl chloride (9 μL; 0.101 mmol) was added dropwise and the reaction was then stirred at room temperature for an additional 5 hours. The reaction was quenched with saturated NaHCO3 solution. The reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was washed twice with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by MPLC (silica gel; 0% to 50% ethyl acetate:hexane gradient) gave the title compound. HPLC/MS: 564.9 (M+1), 566.9 (M+3); Rt=4.33 min.

후처리

  1. stirringthe reaction was then stirred at room temperature for an additional 5 hours
  2. customThe reaction was quenched with saturated NaHCO3 solution
  3. customThe reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution
  4. washThe organic layer was washed twice with saturated NaHCO3 solution, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by MPLC (silica gel; 0% to 50% ethyl acetate:hexane gradient)

출처 및 근거

ORD 기록
ord-465b85b846ba480ab12263322a36681a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091216B2

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