Hydrogen Bromide → N-(3-Fluoro-4-(7-hydroxy-6-methoxyquinolin-4-yloxy)phenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

HRID 15517Notes

Reaction equation

HRID 15517 reaction equation
FC(F)(F)C(O)=O.C([O:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([O:26][C:27]3[CH:32]=[CH:31][C:30]([NH:33][C:34]([C:36]4[C:37](=[O:49])[N:38]([C:42]5[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=5)[CH:39]=[CH:40][CH:41]=4)=[O:35])=[CH:29][C:28]=3[F:50])=[CH:21][CH:22]=[N:23]2)=[CH:18][C:17]=1[O:51][CH3:52])C1C=CC=CC=1.Br.CCOCC>CC(O)=O>[F:50][C:28]1[CH:29]=[C:30]([NH:33][C:34]([C:36]2[C:37](=[O:49])[N:38]([C:42]3[CH:43]=[CH:44][C:45]([F:48])=[CH:46][CH:47]=3)[CH:39]=[CH:40][CH:41]=2)=[O:35])[CH:31]=[CH:32][C:27]=1[O:26][C:20]1[C:19]2[C:24](=[CH:25][C:16]([OH:15])=[C:17]([O:51][CH3:52])[CH:18]=2)[N:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 68682982n-(4-(7-(Benzyloxy)-6-methoxyquinolin-4-yloxy)-3-fluorophenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide trifluoroacetic acid salt

Product 1

HCID 135446414N-(3-Fluoro-4-(7-hydroxy-6-methoxyquinolin-4-yloxy)phenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamideYield 59%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of N-(4-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-3-fluorophenyl)-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide trifluoroacetic acid salt (40 mg, 0.056 mmol) and HBr in HOAc (3 mL of 33% solution) was allowed to stay at rt for 70 minutes. Ether (25 mL) was added to the reaction mixture, stirred for 20 minutes, and the solid was filtered and dried to obtain the product (17 mg, 59%) as a light brown solid. 1H NMR (DMF-d7) δ 12.35 (s, 1H), 8.94 (d, 1H, J=6.6 Hz), 8.70 (d, 1H, J=7.7 Hz), 8.23-7.50 (m, 12H), 7.12 (d, 1H, J=6.6 Hz), 6.84 (m, 1H), 4.17 (s, 3H); MS(ESI+) m/z 516.2 (M+H)+.

Workup

  1. filtrationthe solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-6182f8bd3a9a4655953cde6fdf5b91f2
Source dataset
uspto-grants-2010_06
Patent number
US07732613B2

Reaction notes

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