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

Reaction equation

HRID 8791 reaction equation
[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

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 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

Product 1

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

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-465b85b846ba480ab12263322a36681a
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Linked notes

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