Dimethylformamide → HCID 19592903, compound

HRID 613541Notes

Reaction equation

HRID 613541 reaction equation
S(Cl)(Cl)=O.[CH3:5]N(C)C=O.[Cl:10][C:11]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:12]=1[C:13]([NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[CH:23][C:22]([CH2:26][OH:27])=[C:21]2[N:28]1[CH:32]=[CH:31][N:30]=[CH:29]1)=[O:14].[Na]>CO>[Cl:10][C:11]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:12]=1[C:13]([NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[CH:23][C:22]([CH2:26][O:27][CH3:5])=[C:21]2[N:28]1[CH:32]=[CH:31][N:30]=[CH:29]1)=[O:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 5360545SodiumHCID 19592507HCID 19592507, compound

Product 1

HCID 19592903HCID 19592903, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thionyl chloride (52.8 mg) was dropwise added to dimethylformamide at ambient temperature, and the mixture was stirred for 10 minutes at the same temperature. To the mixture was added 8-(2,6-dichlorobenzoylamino)-3-hydroxymethyl-4-(imidazol-1-yl)quinoline (141 mg), and the mixture was stirred for 20 minutes at ambient temperature. The mixture was partitioned between saturated sodium bicarbonate solution and ethyl acetate, and the organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The obtained residue was dissolved in dichloromethane-methanol, and the solution was added to a solution of sodium methoxide, which was prepared by adding sodium (17.3 mg) to dry methanol (1.5 ml) and then stirring for 15 minutes at ambient temperature. The mixture was stirred for 3 hours at 40° C. The mixture was partitioned between saturated ammonium chloride solution and ethyl acetate, and the organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography to give 8-(2,6-dichlorobenzoylamino)-4-(imidazol-1-yl)-3-(methoxymethyl)quinoline (55 mg).

Workup

  1. stirringthe mixture was stirred for 20 minutes at ambient temperature
  2. customThe mixture was partitioned between saturated sodium bicarbonate solution and ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. dissolutionThe obtained residue was dissolved in dichloromethane-methanol
  7. additionthe solution was added to a solution of sodium methoxide, which
  8. customwas prepared
  9. stirringstirring for 15 minutes at ambient temperature
  10. stirringThe mixture was stirred for 3 hours at 40° C
  11. customThe mixture was partitioned between saturated ammonium chloride solution and ethyl acetate
  12. washthe organic layer was washed with brine
  13. dry with materialdried over magnesium sulfate
  14. customevaporated in vacuo
  15. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-a1f4b7d2db314996bdb1309a59c9f63b
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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