Potassium hydroxy sulfite → 7-({3-[(Dimethylamino)carbonyl]phenyl}sulfinyl)-6-iodo-4-{[3-(methyloxy)phenyl]amino}-3-quinolinecarboxamide

HRID 230857Notes

Reaction equation

HRID 230857 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:18]2[CH:27]=[C:26]3[C:21]([C:22]([NH:31][C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=4)=[C:23]([C:28]([NH2:30])=[O:29])[CH:24]=[N:25]3)=[CH:20][C:19]=2[I:40])[CH:14]=[CH:15][CH:16]=1)=[O:10]>CN(C)C=O>[CH3:41][N:8]([CH3:7])[C:9]([C:11]1[CH:12]=[C:13]([S:17]([C:18]2[CH:27]=[C:26]3[C:21]([C:22]([NH:31][C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=4)=[C:23]([C:28]([NH2:30])=[O:29])[CH:24]=[N:25]3)=[CH:20][C:19]=2[I:40])=[O:1])[CH:14]=[CH:15][CH:16]=1)=[O:10]

Participants

4

Reactant 2

HCID 23707502Potassium hydroxy sulfite2×HCID 577632867-({3-[(Dimethylamino)carbonyl]phenyl}thio)-6-iodo-4-{[3-(methyloxy)phenyl]amino}-3-quinolinecarboxamide

Product 1

HCID 577631957-({3-[(Dimethylamino)carbonyl]phenyl}sulfinyl)-6-iodo-4-{[3-(methyloxy)phenyl]amino}-3-quinolinecarboxamideYield 121.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Oxone (0.5 g) was added portionwise to a stirred solution of Intermediate 64 (0.12 g) in N,N-dimethylformamide (5 ml). The solution was stirred at room temperature under nitrogen for 21 h. More oxone (0.5 g) was added and the mixture was stirred for a further 3 h, quenched with a solution of sodium sulphite (1.5 g) in water (15 ml), diluted with water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined organic extracts were dried over magnesium sulphate and concentrated in vacuo to give the title compound as a yellow solid (0.15 g).

Workup

  1. stirringthe mixture was stirred for a further 3 h
  2. customquenched with a solution of sodium sulphite (1.5 g) in water (15 ml)
  3. additiondiluted with water (50 ml)
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. dry with materialThe combined organic extracts were dried over magnesium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09cedba2b132435eb0c7caee26c2840f
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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