Triethylamine → 7-({3-[(Dimethylamino)carbonyl]phenyl}sulfinyl)-4-{[3-(methyloxy)phenyl]amino}-3-quinolinecarboxamide

HRID 230866Notes

Reaction equation

HRID 230866 reaction equation
[CH3:1][N:2]([CH3:36])[C:3]([C:5]1[CH:6]=[C:7]([S:11]([C:13]2[CH:22]=[C:21]3[C:16]([C:17]([NH:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=4)=[C:18]([C:23]([NH2:25])=[O:24])[CH:19]=[N:20]3)=[CH:15][C:14]=2I)=[O:12])[CH:8]=[CH:9][CH:10]=1)=[O:4].C(N(CC)CC)C>[Pd].C(O)C.CN(C)C=O>[CH3:1][N:2]([CH3:36])[C:3]([C:5]1[CH:6]=[C:7]([S:11]([C:13]2[CH:22]=[C:21]3[C:16]([C:17]([NH:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=4)=[C:18]([C:23]([NH2:25])=[O:24])[CH:19]=[N:20]3)=[CH:15][CH:14]=2)=[O:12])[CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 577631957-({3-[(Dimethylamino)carbonyl]phenyl}sulfinyl)-6-iodo-4-{[3-(methyloxy)phenyl]amino}-3-quinolinecarboxamide

Product 1

HCID 577631927-({3-[(Dimethylamino)carbonyl]phenyl}sulfinyl)-4-{[3-(methyloxy)phenyl]amino}-3-quinolinecarboxamideYield 29.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture containing Intermediate 65 (0.15 g), 10% palladium on activated carbon (0.04 g) and triethylamine (5 ml) in ethanol (25 ml) and N,N-dimethylformamide (10 ml) was hydrogenated at room temperature for 4 h. The suspension was filtered through celite, the residue washed with ethanol/N,N-dimethylformamide (3:1, 50 ml), and the filtrate concentrated in vacuo. The residue was purified by mass directed preparative HPLC (Method A) to give the title compound as a yellow solid (0.035 g).

Workup

  1. filtrationThe suspension was filtered through celite
  2. washthe residue washed with ethanol/N,N-dimethylformamide (3:1, 50 ml)
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was purified by mass

Sources & evidence

ORD record
ord-02b7aeeb05e546a884b75a2f432891db
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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