1-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid → HCID 66779257, compound

HRID 1470363Notes

Reaction equation

HRID 1470363 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([OH:16])=O)[C:9]2=[O:17])=[CH:4][CH:3]=1.[F:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[O:26][C:27]1[CH:32]=[CH:31][N:30]=[C:29]2[CH:33]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:35][C:28]=12)[NH2:22]>>[F:18][C:19]1[CH:20]=[C:21]([NH:22][C:14]([C:10]2[C:9](=[O:17])[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH:13]=[CH:12][CH:11]=2)=[O:16])[CH:23]=[CH:24][C:25]=1[O:26][C:27]1[CH:32]=[CH:31][N:30]=[C:29]2[CH:33]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:35][C:28]=12

Participants

3

Reactant 2

HCID 210815271-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acidHCID 66779743HCID 66779743, compound

Product 1

HCID 66779257HCID 66779257, compound

Procedure

The title compound was prepared by procedure G using 1-(4-fluoro-phenyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid (26.21 mg; 0.11 mmol; 1.20 eq.) instead of 1-(2-hydroxy-2-methyl-propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid and using 3-fluoro-4-[(2-phenylfuro[3,2-b]pyridin-7-yl)oxy]aniline (30.00 mg; 0.09 mmol; 1.00 eq.) instead of 4-[(2-phenylfuro[3,2-b]pyridin-7-yl)oxy]aniline, and was obtained as a beige solid (36 mg, 72%). (HPLC (method F): 89%, RT: 4.63 min); MS (m/z) 536 [M+H]+, RT: 4.2 min.

Sources & evidence

ORD record
ord-59930e628759453cbe184aece9edb094
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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