6-[(4-Chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1-cyclopropylmethyl-4-(3-ethynyl-phenyl)-1H-quinolin-2-one → 3-methyl-3H-imidazol 4-cyclopropylmethyl-4-(3-ethynyl-phenyl)-1H-quinolin-2-one

HRID 1369985Notes

Reaction equation

HRID 1369985 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5](C(O)([C:32]2[N:33]([CH3:37])[CH:34]=[N:35][CH:36]=2)C2C=C3C(=CC=2)N(CC2CC2)C(=O)C=C3C2C=CC=C(C#C)C=2)=[CH:4][CH:3]=1.ClC1C=CC(C2C=C3[C:49]([C:50]([C:59]4[CH:64]=[CH:63][CH:62]=[C:61]([C:65]#[CH:66])[CH:60]=4)=[C:51](C)[C:52](=[O:57])[N:53]3C)=[C:48]([C:67]3N(C)C=NC=3)[C:47]=2O)=CC=1>>[CH3:37][N:33]1[CH:32]=[CH:36][N:35]=[CH:34]1.[CH:48]1([CH2:49][C:50]2([C:59]3[CH:64]=[CH:63][CH:62]=[C:61]([C:65]#[CH:66])[CH:60]=3)[C:7]3[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:53][C:52](=[O:57])[CH2:51]2)[CH2:47][CH2:67]1

Participants

3

Reactant 2

HCID 185164536-[(4-Chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1-cyclopropylmethyl-4-(3-ethynyl-phenyl)-1H-quinolin-2-oneHCID 86585829(4-Chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl-4-(3-ethynyl-phenyl)-1-methyl-1H-quinolin-2-one

Product 1

HCID 865858273-methyl-3H-imidazol 4-cyclopropylmethyl-4-(3-ethynyl-phenyl)-1H-quinolin-2-oneYield 62%

Procedure

The same procedure that was used in example 3 was followed except 6-[(4-Chloro-phenyl) -hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1-cyclopropylmethyl-4-(3-ethynyl-phenyl)-1H-quinolin-2-one (1.80 g, 3.5 mmol) was used in place of 6-[(4-Chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl-4-(3-ethynyl-phenyl)-1-methyl-1H-quinolin-2-one to give 6-[Amino(4chloro-phenyl)-(3-methyl-3H-imidazol-4-cyclopropylmethyl-4-(3-ethynyl-phenyl)-1H-quinolin-2-one (1.12 g, 62%) as a yellow foam.

Sources & evidence

ORD record
ord-2dd30537093d4cec8290fc649336c744
Source dataset
uspto-grants-2003_06
Patent number
US06579887B2

Reaction notes

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