Methyl 2-chloronicotinate → 2-{[2-(3-Methyl-ureido)-pyridin-4-ylmethyl]-amino}-nicotinic acid methyl ester

HRID 602421Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602421
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]([NH:12][CH3:13])=[O:11])[CH:4]=1.[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][C:18]=1Cl>>[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][C:18]=1[NH:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]([NH:12][CH3:13])=[O:11])[CH:4]=1

Komponenten

3

Edukt 2

HCID 819931Methyl 2-chloronicotinateHCID 231188611-(4-Aminomethyl-pyridin-2-yl)-3-methyl-urea

Produkt 1

HCID 586749452-{[2-(3-Methyl-ureido)-pyridin-4-ylmethyl]-amino}-nicotinic acid methyl esterAusbeute 62,8 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 1-(4-aminomethyl-pyridin-2-yl)-3-methyl-urea (3.8 g, 21.1 mmol) and 2-chloro-nicotinic acid methyl ester [Mann et al. J. Chem. Soc.; 1952; 2057, 2060] (1.78 g, 10.4 mmol) was heated for 1 hour at 120° C. The crude product was purified by chromatography on silica gel (Gradient elution: 100% CH2Cl2 to 93% CH2Cl2/7% MeOH) to give 2-{[2-(3-methyl-ureido)-pyridin-4-ylmethyl]-amino}-nicotinic acid methyl ester (2.06 g); Mp. 145-146° C.

Aufarbeitung

  1. customThe crude product was purified by chromatography on silica gel (Gradient elution: 100% CH2Cl2 to 93% CH2Cl2/7% MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-1b831301e89c48e1af27f7b167c5602c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906533B2

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