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

HRID 230856Notes

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]

Participants

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

extractionextracted with ethyl acetate (3×100 ml)
washThe combined organic extracts were washed with water (2×70 ml) and brine (70 ml)
dry with materialdried over magnesium sulphate
concentrationconcentrated in vacuo
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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