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

HRID 415926Notes

Reaction equation

HRID 415926 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[N:14]=[CH:13][CH:12]=[C:11]2[O:20][C:21]1[CH:22]=[CH:23][C:24]([NH:27][C:28]([C:30]2[C:31](=[O:43])[N:32]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:33]=[CH:34][C:35]=2I)=[O:29])=[N:25][CH:26]=1>C(O)(C)C.ClCCl>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[N:14]=[CH:13][CH:12]=[C:11]2[O:20][C:21]1[CH:22]=[CH:23][C:24]([NH:27][C:28]([C:30]2[C:31](=[O:43])[N:32]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:33]=[CH:34][C:35]=2[NH:5][CH2:4][CH2:3][O:2][CH3:1])=[O:29])=[N:25][CH:26]=1

Participants

5

Reactant 2

HCID 80182-MethoxyethylamineHCID 59598356N-(5-(6,7-dimethoxyquinolin-4-yloxy)pyridin-2-yl)-4-iodo-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 45274825N-(5-(6,7-dimethoxyquinolin-4-yloxy)pyridin-2-yl)-4-(2-methoxyethylamino)-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxamideYield 75.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

2-methoxyethylamine (137 μl, 1573 μmol) was added to a suspension of N-(5-(6,7-dimethoxyquinolin-4-yloxy)pyridin-2-yl)-4-iodo-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxamide (122 mg, 197 μmol) in iso-propanol (1 mL). The reaction mixture was heated at 100° C. for 80 min. An aliquot was taken and analyzed by LCMS: The reaction was done. The reaction mixture was diluted with dichloromethane. The crude was adsorbed on silica and purified by MPLC (CH2Cl2/MeOH: 100/0 to 95/5) to afford the title compound N-(5-(6,7-dimethoxyquinolin-4-yloxy)pyridin-2-yl)-4-(2-methoxyethylamino)-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxamide (84 mg, 148 μmol, 75% yield). MS (ESI pos. ion) m/z: 568 (MH+). Calc'd exact mass for C31H29N5O6: 567. 1H NMR (400 MHz, DMSO-d6) 13.28 (s, 1 H), 10.80-10.71 (m, 1 H), 8.49 (d, J=5.2 Hz, 1 H), 8.34 (d, J=9.1 Hz, 1 H), 8.30 (d, J=2.8 Hz, 1 H), 7.79 (dd, J=9.2, 3.1 Hz, 1 H), 7.73 (d, J=7.8 Hz, 1 H), 7.58-7.37 (m, 7 H), 6.53 (d, J=5.2 Hz, 1 H), 6.32 (d, J=8.1 Hz, 1 H), 3.95 (s, 3 H), 3.94 (s, 3 H), 3.64-3.54 (m, 4 H), 3.34 (s, 3 H).

Workup

  1. custompurified by MPLC (CH2Cl2/MeOH: 100/0 to 95/5)

Sources & evidence

ORD record
ord-8a5f4b05f80644b28d717e3a91ccae19
Source dataset
uspto-grants-2012_01
Patent number
US08088794B2

Reaction notes

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