4-(3-chloro-phenyl)-6-[(6-chloro-pyridin-3-yl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1H-quinolin-2-one → 4-(3-Ethoxy-phenyl)-6-(hydroxy-di-pyridin-3-yl-methyl)-1-methyl-1H-quinolin-2-one

HRID 1384366Notes

Reaction equation

HRID 1384366 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([OH:33])([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)[C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[CH:18]=3)[NH:13][C:12](=[O:34])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2].Cl[C:36]1C=C(C2C3C(=CC=C(C(C4C=NC(Cl)=CC=4)(O)C4N(C)C=NC=4)C=3)NC(=O)C=2)C=CC=1>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([OH:33])([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)[CH:18]=3)[N:13]([CH3:36])[C:12](=[O:34])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

3

Reactant 2

HCID 155378354-(3-chloro-phenyl)-6-[(6-chloro-pyridin-3-yl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1H-quinolin-2-oneHCID 224654144-(3-ethoxy-phenyl)-6-(hydroxy-di-pyridin-3-yl-methyl)-1H-quinolin-2-one

Product 1

HCID 224654124-(3-Ethoxy-phenyl)-6-(hydroxy-di-pyridin-3-yl-methyl)-1-methyl-1H-quinolin-2-oneYield 13%

Procedure

The same procedure was used as that in example 2, except that 4-(3-ethoxy-phenyl)-6-(hydroxy-di-pyridin-3-yl-methyl)-1H-quinolin-2-one (91 mg, 0.202 mmol) was used in the place 4-(3-chloro-phenyl)-6-[(6-chloro-pyridin-3-yl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1H-quinolin-2-one to give the title compound of example 37C as a white solid (12 mg, 13% yield).

Sources & evidence

ORD record
ord-ab5d55e27d7b402daa18b52d00b37260
Source dataset
uspto-grants-2001_07
Patent number
US06258824B1

Reaction notes

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