3,4-Dimethoxyphenylboronic acid → 2-(3-Carbamoyl-4-fluorophenylamino)-2-(3,4-dimethoxyphenyl)acetic acid

HRID 1515510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515510
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([F:11])=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].O.[C:26]([OH:30])(=[O:29])[CH:27]=O>C(#N)C.CN(C=O)C>[C:5]([C:4]1[CH:3]=[C:2]([NH:1][CH:27]([C:16]2[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:14]([O:13][CH3:12])[CH:15]=2)[C:26]([OH:30])=[O:29])[CH:10]=[CH:9][C:8]=1[F:11])(=[O:6])[NH2:7]

Komponenten

6

Edukt 3

HCID 27347023,4-Dimethoxyphenylboronic acidHCID 27788995-Amino-2-fluorobenzamideHCID 15620607Glyoxylic acid, monohydrate

Produkt 1

HCID 594793922-(3-Carbamoyl-4-fluorophenylamino)-2-(3,4-dimethoxyphenyl)acetic acidAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3-amino-6-fluorobenzamide (85 mg, 0.5 mmol), 3,4-dimethoxyphenylboronic acid (91 mg, 0.5 mmol) and glyoxylic acid monohydrate (46 mg, 0.5 mmol) in acetonitrile (2.0 mL) and DMF (0.2 mL) was heated at 100° C. for 20 min. in a microwave reactor. After removal of solvent, the crude was triturated with methylene chloride. The precipitate formed was collected by filtration and washed with methylene chloride to give 13A after drying, yield: 46%. 1H NMR (400 MHz, Methanol-d4) δ ppm 3.81 (s, 3H) 3.82 (s, 3H) 4.92 (s, 1H) 6.83-6.89 (m, 1 H) 6.93 (d, J=8.35 Hz, 1H) 6.96-7.02 (m, 1H) 7.03-7.07 (m, 1H) 7.10 (d, J=1.76 Hz, 1H) 7.15 (dd, J=5.93, 2.86 Hz, 1H), LCMS: 349 (M+1).

Aufarbeitung

  1. customAfter removal of solvent
  2. customthe crude was triturated with methylene chloride
  3. customThe precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-d0ff8e8dff6a4a3ca256a73b78a79894
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222453B2

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