1-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid → 1-{4-[1-(4-Fluoro-phenyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-3,4-dihydro-2H-benzo[1,4]oxazin-7-yloxy}-5H-benzo[c][1,8]naphthyridin-6-one

HRID 1029191Notes

Reaction equation

HRID 1029191 reaction equation
[O:1]1[C:6]2[CH:7]=[C:8]([O:11][C:12]3[CH:21]=[CH:20][N:19]=[C:18]4[C:13]=3[C:14]3[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=3[C:16](=[O:22])[NH:17]4)[CH:9]=[CH:10][C:5]=2[NH:4][CH2:3][CH2:2]1.[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40](O)=[O:41])[C:35]2=[O:43])=[CH:30][CH:29]=1>>[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([N:4]3[C:5]4[CH:10]=[CH:9][C:8]([O:11][C:12]5[CH:21]=[CH:20][N:19]=[C:18]6[C:13]=5[C:14]5[CH:26]=[CH:25][CH:24]=[CH:23][C:15]=5[C:16](=[O:22])[NH:17]6)=[CH:7][C:6]=4[O:1][CH2:2][CH2:3]3)=[O:41])[C:35]2=[O:43])=[CH:30][CH:29]=1

Participants

3

Reactant 2

HCID 210815271-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acidHCID 698108831-(3,4-Dihydro-2H-benzo[1,4]oxazin-7-yloxy)-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 581679481-{4-[1-(4-Fluoro-phenyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-3,4-dihydro-2H-benzo[1,4]oxazin-7-yloxy}-5H-benzo[c][1,8]naphthyridin-6-oneYield 83%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 181 using 218 (40 mg, 0.12 mmol) and 1-(4-fluoro-phenyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid (41 mg, 0.17 mmol) to provide 228 (54 mg, 83% yield) as a tan solid. LC-MS (M+H=561, obsd.=561).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-28f0465256a847eb9eaf9bce3f79166c
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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