Dimethylformamide → 4-[(5-Chloro-2-pyridinyl)methoxy]-1-(4-{2-[isopropyl(methyl)amino]ethoxy}-phenyl)-1H-pyridin-2-one

HRID 15079

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-[4-(2-bromoethoxy)phenyl]-4-[(5-chloro-2-pyridinyl)methoxy]-1H-pyridin-2-one (1.1 g, 2.6 mmols, Step (1) of Example 109), isopropyl(methyl)amine (0.811 mL, 7.8 mmols) and DMF (2.6 mL) was stirred at 60° C. for 2 days. Water was added to the reaction liquid and filtered. So obtained crude title compound was purified on silica gel column chromatography (KP-Sil FLASH 25+M, chloroform:methanol=1:0→5:1) to provide the title compound (1.1 g, 99%).

Workup

filtrationfiltered
customSo obtained crude title compound
customwas purified on silica gel column chromatography (KP-Sil FLASH 25+M, chloroform:methanol=1:0→5:1)

Sources & evidence

ORD record: ord-931df4c3aadd420e897071d9b62616a7
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732456B2

Linked notes

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