1-Hydroxybenzotriazole → N-[2-(4-Methoxy-phenyl)-2-oxo-ethyl]-isophthalamic Acid Methylester

HRID 349435

Reaktionsgleichung

Reaktionsgleichung von HRID 349435
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=O)[CH:5]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:37][CH2:38][C:39]([C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1)=[O:40].C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([NH:37][CH2:38][C:39]([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=2)=[O:40])=[O:9])[CH:5]=1

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 124871882-Amino-4'-methoxyacetophenone hydrochloride

Produkt 1

HCID 58804856N-[2-(4-Methoxy-phenyl)-2-oxo-ethyl]-isophthalamic Acid MethylesterAusbeute 194,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.8 g (5.5 mmol) of isophthalic acid monomethyl ester from Preparation 1, 3.5 g (18.5 mmol) of EDAC.HCl, 2.5 g (18.5 mmol) of HOBt, and 3.1 g (15.4 mmol) of 2-amino-1-(4-methoxy-phenyl)-ethanone hydrochloride were dissolved in 20 mL of dimethylformamide. 1.9 g (15.4 mmol) of di-isopropyl ethylamine was then added. Stirring was continued overnight at room temperature. Water (60 ml) was added, and the product was filtered, washed with water. The resulting solid was triturated in hot methanol, filtered and dried in a vacuum oven overnight at 70° C. to provide 3.5 g (69%) desired product. MS: m/z (APCI, AP+) 328 [M−]+ NMR: DMSO 1H δ (ppm) 3.84 (3H, s); 3.88 (3H, s); 4.73 (2H, d, J=5.6 Hz); 7.04–7.08 (2H m); 7.63–7.66 (1H, t, J=7.8 Hz); 7.99–8.027 (2H, m); 8.097–8.16 (2H, m); 8.47–8.48 (1H, m); 9.00–9.03 (1H, t, J=5.8 Hz).

Aufarbeitung

  1. filtrationthe product was filtered
  2. washwashed with water
  3. customThe resulting solid was triturated in hot methanol
  4. filtrationfiltered
  5. customdried in a vacuum oven overnight at 70° C.

Quellen und Nachweise

ORD-Eintrag
ord-2f27bebcb9c2437aa7b69dd765c0cc0e
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179822B2

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