Dimethylformamide → 5-(4-Chlorophenyl)-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)furan-2-carboxamide

HRID 1951252

Reaktionsgleichung

Reaktionsgleichung von HRID 1951252
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:17][C:18]1[CH:19]=[C:20]([CH:27]=[CH:28][C:29]=1[CH3:30])[C:21]([NH:23][CH:24]1[CH2:26][CH2:25]1)=[O:22].CN(C=O)C>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([C:13]([NH:17][C:18]3[CH:19]=[C:20]([C:21](=[O:22])[NH:23][CH:24]4[CH2:26][CH2:25]4)[CH:27]=[CH:28][C:29]=3[CH3:30])=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 7266935-(4-Chlorophenyl)-2-furoic acidHCID 442031943-Amino-N-cyclopropyl-4-methylbenzamide hydrochloride

Produkt 1

HCID 597613905-(4-Chlorophenyl)-N-(5-(cyclopropylcarbamoyl)-2-methylphenyl)furan-2-carboxamideAusbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 5-(4-chlorophenyl)furan-2-carboxylic acid (45 mg, 0.20 mmol) and 3-amino-N-cyclopropyl-4-methylbenzamide hydrochloride (prepared as described in WO 04/071440) (50 mg, 0.22 mmol) in DMF (0.5 mL) DIPEA (0.105 mL, 0.6 mmol) and the resulting mixture was stirred at rt for 1 h then at 80° C. for 1 h. The reaction was cooled to rt and water (3 mL) was added and the crude product was collected by vacuum filtration and dried under vacuum to afford 78 mg of a tan solid. The crude product was recrystallized from CH2Cl2 to afford 48 mg of a light tan solid as the title compound (Example 127). HPLC Ret. Time=3.52 min, LCMS [M+H]+ 395.23.

Aufarbeitung

  1. filtrationthe crude product was collected by vacuum filtration
  2. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-40f064ff8fea4e9cbb3a914b6939ab0e
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404689B2

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