1-(2-Hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazole-4-carboxylic Acid → 1-(2-Hydroxy-2-methyl-propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid [3-fluoro-4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-amide

HRID 1029174Notes

Reaction equation

HRID 1029174 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:16]=[CH:15][N:14]=[C:13]3[C:8]=2[C:9]2[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=2[C:11](=[O:17])[NH:12]3)=[C:4]([F:24])[CH:3]=1.[OH:25][C:26]([CH3:45])([CH3:44])[CH2:27][N:28]1[C:32]([CH3:33])=[C:31]([C:34](O)=[O:35])[C:30](=[O:37])[N:29]1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[F:24][C:4]1[CH:3]=[C:2]([NH:1][C:34]([C:31]2[C:30](=[O:37])[N:29]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:28]([CH2:27][C:26]([OH:25])([CH3:45])[CH3:44])[C:32]=2[CH3:33])=[O:35])[CH:23]=[CH:22][C:5]=1[O:6][C:7]1[CH:16]=[CH:15][N:14]=[C:13]2[C:8]=1[C:9]1[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=1[C:11](=[O:17])[NH:12]2

Participants

3

Reactant 2

HCID 533934301-(2-Hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazole-4-carboxylic AcidHCID 581683451-(4-Amino-2-fluoro-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-one

Product 1

HCID 581683531-(2-Hydroxy-2-methyl-propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid [3-fluoro-4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-amideYield 33.7%

Procedure

The title compound was synthesized according to the procedure described for the preparation of Example 209 using Compound 182 (55 mg, 0.17 mmol) and 1-(2-hydroxy-2-methyl-propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (60 mg, 0.21 mmol) to provide 210 (34 mg, 33% yield) as a white solid. LC-MS (M+H=594, obsd.=594).

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-36fbb6de4a5e442999b86818ce3501eb
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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