Sodium Hydroxide → 3-Methyl-2-[2-(4-amidinophenyl)ethyl]imidazo[4,5-b]pyridine-6-carboxylic acid-N-phenyl-N-(2-hydroxycarbonylethyl)amide

HRID 50193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 50193
[C:1]1([N:7]([CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])[C:8]([C:10]2[CH:11]=[C:12]3[N:18]=[C:17]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][C:24]([C:27](=[NH:29])[NH2:28])=[CH:23][CH:22]=4)[N:16]([CH3:30])[C:13]3=[N:14][CH:15]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C.O>[C:1]1([N:7]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])[C:8]([C:10]2[CH:11]=[C:12]3[N:18]=[C:17]([CH2:19][CH2:20][C:21]4[CH:22]=[CH:23][C:24]([C:27](=[NH:28])[NH2:29])=[CH:25][CH:26]=4)[N:16]([CH3:30])[C:13]3=[N:14][CH:15]=2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 158702323-Methyl-2-[2-(4-amidinophenyl)ethyl]-imidazo[4,5-b]-pyridine-6-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)-amide

Produkt 1

HCID 158702333-Methyl-2-[2-(4-amidinophenyl)ethyl]imidazo[4,5-b]pyridine-6-carboxylic acid-N-phenyl-N-(2-hydroxycarbonylethyl)amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 535 mg (1.0 mmol) of 3-methyl-2-[2-(4-amidinophenyl)ethyl]imidazo[4,5-b]pyridine-6-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide in 10 mL ethanol was mixed with 5 mL of 2N sodium hydroxide solution and stirred for 2 hours at room temperature. Then the mixture was diluted with 10 mL water, the alcohol was distilled off, the aqueous phase was washed with 20 mL ethyl acetate and acidified with concentrated hydrochloric acid, whereupon the desired compound was precipitated in the form of white crystals. Yield: 375 mg (74% of theory), C26H26N6O3 (470.54); Rf value: 0.23 (silica gel; ethyl acetate/ethanol/ammonia=90:5:5); mass spectrum: (M+H)+=471.

Aufarbeitung

  1. distillationthe alcohol was distilled off
  2. washthe aqueous phase was washed with 20 mL ethyl acetate
  3. customwas precipitated in the form of white crystals

Quellen und Nachweise

ORD-Eintrag
ord-2fcd82643328441b90d2b76c0fea57f0
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710055B2

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