Diisopropylethylamine → Methyl 4-[3-(4-cyanobenzoyl)ureido]phenoxyacetate

HRID 1900873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900873
Cl.[NH2:2][C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[C:24]([C:26]1[CH:36]=[CH:35][C:29]([C:30]([N:32]=[C:33]=[O:34])=[O:31])=[CH:28][CH:27]=1)#[N:25]>C(#N)C>[C:24]([C:26]1[CH:27]=[CH:28][C:29]([C:30]([NH:32][C:33](=[O:34])[NH:2][C:3]2[CH:4]=[CH:5][C:6]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:13][CH:14]=2)=[O:31])=[CH:35][CH:36]=1)#[N:25]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 149137394-Cyanobenzoyl isocyanateHCID 18918265Methyl (4-aminophenoxy)acetate hydrochloride

Produkt 1

HCID 23370013Methyl 4-[3-(4-cyanobenzoyl)ureido]phenoxyacetateAusbeute 52,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

Methyl 4-aminophenoxyacetate, hydrochloride salt (1.09 g), was dissolved, with warming, in acetonitrile (50 ml) containing diisopropylethylamine (0.86 ml). To this solution at ambient temperature was added gradually with stirring a solution of 4-cyanobenzoyl isocyanate (1 g, preparation described in Weikert, R. J. et al (1991), J. Med. Chem. 34, 1630) in acetonitrile (5 ml). The precipitated solid was crystallised from boiling acetonitrile to give methyl 4-[3-(4-cyanobenzoyl)ureido]phenoxyacetate (930 mg) as an off-white solid: m.p. 214°-217° C.; NMR Spectrum (DMSO-d6) 3.70 (3H, s), 4.77 (2H, s), 6.94 (2H, d), 7.48 (2H, d), 8.02 (2H, d), 8.12 (2H, d), 10.49 (1H, s), 11.19 (1H, s); Mass Spectrum m/Z 354 (M+H)+.

Aufarbeitung

  1. additionTo this solution at ambient temperature was added gradually
  2. customThe precipitated solid was crystallised

Quellen und Nachweise

ORD-Eintrag
ord-8135e09261b04ed7a509324ad1fabe8c
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576334

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