Diisopropylethylamine → N-(5-(6,7-dimethoxyquinolin-4-yloxy)pyridin-2-yl)-4-iodo-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxamide

HRID 415925Notes

Reaction equation

HRID 415925 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4](=[O:14])[C:3]=1[C:15](Cl)=[O:16].C(N(C(C)C)CC)(C)C.[CH3:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[N:35]=[CH:34][CH:33]=[C:32]2[O:41][C:42]1[CH:43]=[CH:44][C:45]([NH2:48])=[N:46][CH:47]=1>ClCCl.CO>[CH3:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[N:35]=[CH:34][CH:33]=[C:32]2[O:41][C:42]1[CH:43]=[CH:44][C:45]([NH:48][C:15]([C:3]2[C:4](=[O:14])[N:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:6]=[CH:7][C:2]=2[I:1])=[O:16])=[N:46][CH:47]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 229365375-(6,7-Dimethoxyquinolin-4-yloxy)pyridin-2-amineHCID 866255464-Iodo-2-oxo-1-phenyl-1,2-dihydropyridine-3-carbonyl chloride

Product 1

HCID 59598356N-(5-(6,7-dimethoxyquinolin-4-yloxy)pyridin-2-yl)-4-iodo-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxamideYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-iodo-2-oxo-1-phenyl-1,2-dihydropyridine-3-carbonyl chloride (139 mg, 387 μmol) in dichloromethane (4 mL) at room temperature was added diisopropylethylamine (202 μl, 1160 μmol) followed by 5-(6,7-dimethoxyquinolin-4-yloxy)pyridin-2-amine (115 mg, 387 μmol). The reaction mixture was stirred at room temperature for 2 h. An aliquot was taken and analyzed by LCMS: reaction was done. The reaction mixture was diluted with methanol and directly adsorbed on silica. Purification by MPLC (CH2Cl2/MeOH: 100/0 to 96/4) afforded N-(5-(6,7-dimethoxyquinolin-4-yloxy)pyridin-2-yl)-4-iodo-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxamide (162 mg, 261 μmol, 68% yield for two steps). MS (ESI pos. ion) m/z: 621 (MH+). Calc'd exact mass for C28H20IN4O5: 620.

Workup

  1. customreaction
  2. customPurification by MPLC (CH2Cl2/MeOH: 100/0 to 96/4)

Sources & evidence

ORD record
ord-ad71b1651b0349f3b42870fae271a23b
Source dataset
uspto-grants-2012_01
Patent number
US08088794B2

Reaction notes

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