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

HRID 230856
Notes
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Reaction equation

HRID 230856 reaction equation
Cl.Cl[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)=[C:8]([C:13]([NH2:15])=[O:14])[CH:9]=[N:10]2)=[CH:5][C:4]=1[I:25].[SH:26][C:27]1[CH:28]=[C:29]([CH:35]=[CH:36][CH:37]=1)[C:30]([N:32]([CH3:34])[CH3:33])=[O:31].C(=O)([O-])[O-].[K+].[K+]>CN1CCCN(C)C1=O.O>[CH3:33][N:32]([CH3:34])[C:30]([C:29]1[CH:28]=[C:27]([S:26][C:3]2[CH:12]=[C:11]3[C:6]([C:7]([NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=4)=[C:8]([C:13]([NH2:15])=[O:14])[CH:9]=[N:10]3)=[CH:5][C:4]=2[I:25])[CH:37]=[CH:36][CH:35]=1)=[O:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 577632243-Mercapto-N,N-dimethylbenzamide2×HCID 674243377-Chloro-6-iodo-4-{[3-(methyloxy)phenyl]amino}-3-quinolinecarboxamide hydrochloride

Product 1

HCID 577632867-({3-[(Dimethylamino)carbonyl]phenyl}thio)-6-iodo-4-{[3-(methyloxy)phenyl]amino}-3-quinolinecarboxamideYield 24.6%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of Intermediate 63 (0.4 g), Intermediate 28 (0.16 g) and potassium carbonate (0.38 g) in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (10 ml) was heated at 100° C. under nitrogen for 3 h. A further portion of Intermediate 28 (0.07 g) was added and the mixture stirred at 60° C. for 23 h. The cooled mixture was diluted with water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with water (2×70 ml) and brine (70 ml), dried over magnesium sulphate and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with methanol followed by mass directed preparative HPLC (Method A) to give the title compound as a yellow foam (0.12 g).

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. washThe combined organic extracts were washed with water (2×70 ml) and brine (70 ml)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel eluting with methanol

Sources & evidence

ORD record
ord-71e2ed784a8341b3a479f2e57e494948
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07566786B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes