O-Methylhydroxylamine hydrochloride → 1-ethyl-3-[7-[(E)-N-methoxy-C-methylcarbonimidoyl]-5-phenylmethoxy-1,3-benzothiazol-2-yl]urea

HRID 712288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 712288
Cl.[CH3:2][O:3][NH2:4].[C:5]([C:8]1[C:16]2[S:15][C:14]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:13][C:12]=2[CH:11]=[C:10]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:9]=1)(=O)[CH3:6]>CN(C=O)C>[CH2:24]([O:23][C:10]1[CH:9]=[C:8](/[C:5](/[CH3:6])=[N:4]/[O:3][CH3:2])[C:16]2[S:15][C:14]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:13][C:12]=2[CH:11]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Komponenten

4

Edukt 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 866640001-(7-Acetyl-5-benzyloxy-1,3-benzothiazol-2-yl)-3-ethyl-urea

Produkt 1

HCID 872225491-ethyl-3-[7-[(E)-N-methoxy-C-methylcarbonimidoyl]-5-phenylmethoxy-1,3-benzothiazol-2-yl]ureaAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

O-Methyl hydroxylamine hydrochloride (289 mg, 3.46 mmol) was added to 1-(7-acetyl-5-benzyloxy-1,3-benzothiazol-2-yl)-3-ethyl-urea (650 mg, 1.73 mmol) in DMF (7 mL). The reaction mixture was heated to 60° C. for 2 h after which time LCMS indicated clean conversion to the desired product. The reaction was diluted with EtOAc, washed with water then brine and the organic layer dried (MgSO4), filtered and the solvent removed in vacuo to give the desired compound an off white solid, 550 mg, 78% yield.

Quellen und Nachweise

ORD-Eintrag
ord-67d78661df944640bd8ecb4789f31215
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181234B2

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