Triethylamine → 3-Bromo-4-fluoro-5-methanesulfonyl-N-methyl-N-propyl-benzamide

HRID 732511

Reaktionsgleichung

Reaktionsgleichung von HRID 732511
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:12]([CH3:15])(=[O:14])=[O:13])[C:10]=1[F:11])[C:5]([OH:7])=O.Cl.[CH3:17][N:18](C)[CH2:19][CH2:20][CH2:21]N=C=NCC.ON1C2C=CC=CC=2N=N1.CNCCC.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:12]([CH3:15])(=[O:14])=[O:13])[C:10]=1[F:11])[C:5]([N:18]([CH3:17])[CH2:19][CH2:20][CH3:21])=[O:7]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 12315N-MethylpropylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 688147113-Bromo-4-fluoro-5-methanesulfonylbenzoic acid

Produkt 1

HCID 688173883-Bromo-4-fluoro-5-methanesulfonyl-N-methyl-N-propyl-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Mix 3-bromo-4-fluoro-5-methanesulfonylbenzoic acid (1.6 g, 5.04 mmol), 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride (968 mg, 5.04 mmol) and 1-hydroxybenzotriazole (680 mg, 5.04 mmol) in DMF (20 mL) at room temperature for 20 min. Add methyl-propylamine (368 mg, 5.04 mmol) and triethylamine (520 mg, 15.1 mmol) and stir at room temperature for 1 h. Dilute with ethyl acetate, wash with 10% aqueous potassium carbonate, 0.1 N citric acid, 1 N lithium chloride and saturated aqueous sodium chloride, concentrate and purify (silica gel chromatography, eluting with 10:90 to 50:50 ethyl acetate:hexanes) to give the title compound as an oil.

Aufarbeitung

  1. washwash with 10% aqueous potassium carbonate, 0.1 N citric acid, 1 N lithium chloride and saturated aqueous sodium chloride
  2. concentrationconcentrate
  3. custompurify
  4. wash(silica gel chromatography, eluting with 10:90 to 50:50 ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-dfd1952a42df48efad81fb2895a0dd69
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585885B2

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