3-Aminobenzamide → 2-(3-Carbamoylphenylamino)-2-(3,4-dimethoxyphenyl)acetic acid

HRID 1515496

Reaktionsgleichung

Reaktionsgleichung von HRID 1515496
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].[CH3:11][O:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20].O.[C:25]([OH:29])(=[O:28])[CH:26]=O>C(#N)C.CN(C=O)C>[C:5]([C:4]1[CH:3]=[C:2]([NH:1][CH:26]([C:15]2[CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:13]([O:12][CH3:11])[CH:14]=2)[C:25]([OH:29])=[O:28])[CH:10]=[CH:9][CH:8]=1)(=[O:6])[NH2:7]

Komponenten

6

Edukt 3

HCID 16453-AminobenzamideHCID 27347023,4-Dimethoxyphenylboronic acidHCID 15620607Glyoxylic acid, monohydrate

Produkt 1

HCID 598380342-(3-Carbamoylphenylamino)-2-(3,4-dimethoxyphenyl)acetic acidAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A mixture of 3-aminobenzamide (204 mg, 1.5 mmol), 3,4-dimethoxyphenylboronic acid (273 mg, 1.5 mmol) and glyoxylic acid monohydrate (138 mg, 1.5 mmol) in acetonitrile (8.0 mL) and DMF (0.8 mL) was heated at 55° C. for 4.0 h and then stirred at rt for 18 h. The precipitate formed was collected by filtration and washed with ethyl acetate to give 1A (390 mg, 78% yield) after drying. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.03-7.19 (m, 5H) 6.91 (d, J=9.0 Hz, 1H) 6.81 (d, J=8.00 Hz, 1H) 5.05 (s, 1H) 3.83 (s, 3H) 3.72 (s, 3H). LC-MS 331 (M+H).

Aufarbeitung

  1. customThe precipitate formed
  2. filtrationwas collected by filtration
  3. washwashed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-cece7e8876514a6f9811a97e82b4b072
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222453B2

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