1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → benzyl N'-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carbonyl]hydrazinecarboxylate

HRID 71181

Reaktionsgleichung

[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([O-:11])=O)[CH:6]=[CH:5][C:4]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1.[Na+].[NH:19]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[NH2:20].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(=O)([O-])O.[Na+]>CN(C=O)C.[Cl-].[Na+].O.O>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([NH:20][NH:19][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])=[O:11])[CH:6]=[CH:5][C:4]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a mixture of sodium 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carboxylate (12.7 g), benzyl hydrazinecarboxylate (9.10 g) and HOBt (7.4 g) in DMF (250 mL) was added WSC (8.50 g) at 0° C., and the mixture was stirred at 0° C. for 1 hr. Saturated aqueous sodium hydrogen carbonate solution (200 mL), water (400 mL) and saturated brine solution (200 mL) were added to the reaction mixture at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous' magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with ethyl acetate and dried to give the title compound (14.6 g).

Aufarbeitung

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous' magnesium sulfate
customthe solvent was evaporated under reduced pressure
washThe residue was washed with ethyl acetate
customdried

Quellen und Nachweise

ORD-Eintrag: ord-eee2011ed9584e55be3b67295bb12adf
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08822699B2

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