Triethylamine → benzoic acid N'-[3-(3-bromo-phenyl)-propionyl]-N'-isopropyl-hydrazide

HRID 1724163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1724163
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][CH:7]=1.[CH:13]([NH:16][NH:17][C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:15])[CH3:14].C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([N:16]([CH:13]([CH3:15])[CH3:14])[NH:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:12])[CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 188691-Benzoyl-2-isopropylhydrazineHCID 757711-HydroxybenzotriazoleHCID 20638623-(3-bromophenyl)propanoic Acid

Produkt 1

HCID 57560133benzoic acid N'-[3-(3-bromo-phenyl)-propionyl]-N'-isopropyl-hydrazideAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (3-(3-bromophenyl)propionic acid (257 mg, 1.12 mmoles) and benzoic acid N′-isopropyl-hydrazide (200 mg, 1.12 mmoles) in DMF (6 mL) was treated with triethylamine (0.47 mL, 3.36 mmoles), HOBT (182 mg, 1.34 mmoles) and EDCI (2.58 mg, 1.34 mmoles) at room temperature for 18 h. The reaction mixture was partitioned between water and dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 20-40% ethyl acetate/hexanes gradient to afford the product as a solid (293 mg, 67%).

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with a 20-40% ethyl acetate/hexanes gradient

Quellen und Nachweise

ORD-Eintrag
ord-c5ce0e9a4c4b4820b85654d5e825840b
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485752B2

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