Triethylamine → 3-hydroxy-4-fluoro-N-cyclopropylbenzamide

HRID 1985754

Reaktionsgleichung

Reaktionsgleichung von HRID 1985754
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=O.[CH:12]1([NH2:15])[CH2:14][CH2:13]1.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.O>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([NH:15][CH:12]1[CH2:14][CH2:13]1)=[O:7]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 5936354-Fluoro-3-hydroxybenzoic acid

Produkt 1

HCID 220191063-hydroxy-4-fluoro-N-cyclopropylbenzamideAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 3-hydroxy-4-fluorobenzoic acid (1.56 g, 10 mmol), cyclopropylamine (0.6 g, 10.5 mmol), triethylamine (1.02 g, 10 mmol) and HOBt (0.3 g, 2 mol) in DMF (10 mL) was added EDCI (2.0 g, 10.5 mmol) at RT. The mixture was stirred at RT overnight. The mixture was diluted with water and extracted with ethyl acetate (3×20 mL). The extract was washed with water and concentrated to afford 3-hydroxy-4-fluoro-N-cyclopropylbenzamide as a solid (1.2 g, 61.5%).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe extract was washed with water
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d18369ac9f1342f2975f0ae666a0b447
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547711B2

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