2-Bromo-N-(5-chloro-2-pyridinyl)acetamide → HCID 67011891, Verbindung

HRID 18553

Reaktionsgleichung

Reaktionsgleichung von HRID 18553
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]([C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([S:22]([CH2:25][CH2:26][OH:27])(=[O:24])=[O:23])=[CH:21][C:15]=3[N:14]=2)=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].Br[CH2:29][C:30]([NH:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][N:34]=1)=[O:31].CC#N.O>C(O)=O>[CH:1]([N:4]1[CH2:5][CH2:6][CH:7]([NH:10][C:11]([C:13]2[N:17]([CH2:29][C:30](=[O:31])[NH:32][C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][N:34]=3)[C:16]3[CH:18]=[CH:19][C:20]([S:22]([CH2:25][CH2:26][OH:27])(=[O:23])=[O:24])=[CH:21][C:15]=3[N:14]=2)=[O:12])[CH2:8][CH2:9]1)([CH3:3])[CH3:2].[CH:1]([N:4]1[CH2:5][CH2:6][CH:7]([NH:10][C:11]([C:13]2[N:14]([CH2:29][C:30](=[O:31])[NH:32][C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][N:34]=3)[C:15]3[CH:21]=[C:20]([S:22]([CH2:25][CH2:26][OH:27])(=[O:23])=[O:24])[CH:19]=[CH:18][C:16]=3[N:17]=2)=[O:12])[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 34211102-Bromo-N-(5-chloro-2-pyridinyl)acetamideHCID 18373917Acetonitrile--water (1/1)HCID 178456285HCID 178456285, Verbindung

Produkt 2

HCID 67011891HCID 67011891, VerbindungHCID 670133221-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-6-(2-hydroxy-ethanesulfonyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-5-(2-hydroxy-ethanesulfonyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide and 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-6-(2-hydroxy-ethanesulfonyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide were prepared by a procedure according to example 29 starting from 1 g (2.5 mmol) crude 5-(2-hydroxy-ethanesulfonyl)-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide and 758.9 mg (3.04 mmol) 2-bromo-N-(5-chloro-pyridin-2-yl)-acetamide. Preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid) gave a 1:1 mixture of both isomers described in the title. These isomers could be separated by NP-HPLC using a chiral stationary phase and a mixture of heptane, ethanol, methanol and diethyl amine as solvent. Structural assignment of both isomers was achieved by NOE-spectroscopy.

Aufarbeitung

  1. additiona 1:1 mixture of both isomers
  2. customThese isomers could be separated by NP-HPLC
  3. additiona mixture of heptane, ethanol, methanol and diethyl amine as solvent

Quellen und Nachweise

ORD-Eintrag
ord-e3c9e4155de642c1a2392901f60027ef
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741341B2

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