Bromomethylcyclopropane → 6-[(6-Chloro-Pyridin-3-yl)-Hydroxy-(3-Methyl-3H-Imidazol-4-yl)-Methyl]-1-Cyclopropylmethyl-4-(3-Ethoxy-Phenyl)-1H-Quinolin-2-One

HRID 50169Notes

Reaction equation

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

Participants

Reactant 2

HCID 81503Bromomethylcyclopropane

HCID 224653976-[(6-Chloro-Pyridin-3-yl)-Hydroxy-(3-Methyl-3H-Imidazol-4-yl)-Methyl]-4-(3-Ethoxy-Phenyl)-1H-Quinolin-2-One

Product 1

HCID 224654136-[(6-Chloro-Pyridin-3-yl)-Hydroxy-(3-Methyl-3H-Imidazol-4-yl)-Methyl]-1-Cyclopropylmethyl-4-(3-Ethoxy-Phenyl)-1H-Quinolin-2-OneYield 7.2%

Procedure

The same procedure described in example 8, 6-[(6-chloro-pyridin-3-yl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-4-(3-ethoxy-phenyl)-1H-quinolin-2-one (50 mg, 0.103 mmol) and (bromomethyl)cyclopropane (0.020 ml, 0.206 mmol) generated the title compound as a white solid (4 mg, 7% yield).

Sources & evidence

ORD record: ord-509f88a7079343d3b2e053c1355d64d3
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06710209B2

Reaction notes

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