(3-Carbamoylphenyl)boronic acid → 3-{4-(5-Chlorothiophen-2-yl)-2-[2-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)ethylamino]pyrimidin-5-yl}benzamide

HRID 507587Notes

Reaction equation

HRID 507587 reaction equation
Br[C:2]1[C:3]([C:20]2[S:21][C:22]([Cl:25])=[CH:23][CH:24]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[NH:13][C:12]2=[O:19])=[N:6][CH:7]=1.[C:26]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)(=[O:28])[NH2:27]>>[Cl:25][C:22]1[S:21][C:20]([C:3]2[C:2]([C:33]3[CH:34]=[C:29]([CH:30]=[CH:31][CH:32]=3)[C:26]([NH2:27])=[O:28])=[CH:7][N:6]=[C:5]([NH:8][CH2:9][CH2:10][N:11]3[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[NH:13][C:12]3=[O:19])[N:4]=2)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 2737814(3-Carbamoylphenyl)boronic acidHCID 602044701-{2-[5-Bromo-4-(5-chlorothiophen-2-yl)pyrimidin-2-ylamino]ethyl}-5,5-dimethylimidazolidine-2,4-dione

Product 1

HCID 602044873-{4-(5-Chlorothiophen-2-yl)-2-[2-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)ethylamino]pyrimidin-5-yl}benzamide

Procedure

The title compound was prepared from 1-{2-[5-bromo-4-(5-chlorothiophen-2-yl)pyrimidin-2-ylamino]ethyl}-5,5-dimethylimidazolidine-2,4-dione and 3-carbamoylphenylboronic acid in a manner analogous to Example 269. MS (M+H)+ 485.

Sources & evidence

ORD record
ord-e851477119474b9dac03458522e99a53
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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