Reaktion #689603

ord-1b831301e89c48e1af27f7b167c5602c

Reaktionsgleichung

CNC(=O)Nc1cc(CN)ccn1
1-(4-aminomethyl-pyridin-2-yl)-3-methyl-urea
COC(=O)c1cccnc1Cl
2-chloro-nicotinic acid methyl ester
CNC(=O)Nc1cc(CNc2ncccc2C(=O)OC)ccn1
2-{[2-(3-methyl-ureido)-pyridin-4-ylmethyl]-amino}-nicotinic acid methyl ester
Ausbeute 62.8%

Reaktionsbedingungen

Temperatur
120°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07906533B2uspto-grants-2011_03