Potassium hydroxy sulfite → 7-({3-[(Dimethylamino)carbonyl]phenyl}sulfonyl)-4-{[3-(methyloxy)phenyl]amino}-3-quinolinecarboxamide

HRID 230867Notes

Reaction equation

HRID 230867 reaction equation
[OH:1]OS([O-])=O.[K+].[CH3:7][N:8]([CH3:41])[C:9]([C:11]1[CH:12]=[C:13]([S:17]([C:19]2[CH:28]=[C:27]3[C:22]([C:23]([NH:32][C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=4)=[C:24]([C:29]([NH2:31])=[O:30])[CH:25]=[N:26]3)=[CH:21][CH:20]=2)=[O:18])[CH:14]=[CH:15][CH:16]=1)=[O:10]>CN(C)C=O>[CH3:7][N:8]([CH3:41])[C:9]([C:11]1[CH:12]=[C:13]([S:17]([C:19]2[CH:28]=[C:27]3[C:22]([C:23]([NH:32][C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=4)=[C:24]([C:29]([NH2:31])=[O:30])[CH:25]=[N:26]3)=[CH:21][CH:20]=2)(=[O:1])=[O:18])[CH:14]=[CH:15][CH:16]=1)=[O:10]

Participants

4

Reactant 2

HCID 23707502Potassium hydroxy sulfite2×HCID 577631927-({3-[(Dimethylamino)carbonyl]phenyl}sulfinyl)-4-{[3-(methyloxy)phenyl]amino}-3-quinolinecarboxamide

Product 1

HCID 577632017-({3-[(Dimethylamino)carbonyl]phenyl}sulfonyl)-4-{[3-(methyloxy)phenyl]amino}-3-quinolinecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Oxone (0.22 g) was added portionwise to a stirred solution of Example 575 (0.035 g) in N,N-dimethylformamide (4 ml). The mixture was stirred at room temperature under nitrogen for 24 h, a further portion of oxone (0.17 g) was added, and the mixture stirred for a further 5 h. The reaction was quenched with a solution of sodium sulphite (1.2 g) in water (15 ml), diluted with water (10 ml) and extracted with ethyl acetate (3×30 ml). The combined organic extracts were dried over magnesium sulphate and concentrated in vacuo to give the title compound as a buff solid (0.035 g).

Workup

  1. stirringthe mixture stirred for a further 5 h
  2. customThe reaction was quenched with a solution of sodium sulphite (1.2 g) in water (15 ml)
  3. additiondiluted with water (10 ml)
  4. extractionextracted with ethyl acetate (3×30 ml)
  5. dry with materialThe combined organic extracts were dried over magnesium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-169244b44fb0426888e5347f6e7a77e8
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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