3-Aminopyridine → HCID 69936592, Verbindung

HRID 1623750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1623750
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[C:13]([CH:17]=1)[C:14](O)=[O:15].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[C:13]([CH:17]=1)[C:14]([NH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)=[O:15]

Komponenten

6

Edukt 4

HCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 3251205-Bromo-2-[(4-chlorophenyl)methoxy]benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 69936592HCID 69936592, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Solid pyridin-3-amine (99 mg, 1.05 mmol) was added in one charge to a stirred solution of 5-bromo-2-(4-chlorobenzyloxy)benzoic acid (may be prepared as described in Description 16, 180 mg, 0.53 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (121 mg, 0.63 mmol) and 1-Hydroxybenzotriazole (85 mg, 0.63 mmol) in DMF (15 ml) under nitrogen at 20° C. The reaction mixture was stirred at 20° C. for 16 h. The organic phase was washed with water (25 ml), extracted with ethyl acetate (3×30 ml), dried over sodium sulphate, evaporated in vacuo and purified by column chromatography (petroleum ether:ethyl acetate=1.5:1) to yield the title compound as a white solid. 200 mg.

Aufarbeitung

  1. washThe organic phase was washed with water (25 ml)
  2. extractionextracted with ethyl acetate (3×30 ml)
  3. dry with materialdried over sodium sulphate
  4. customevaporated in vacuo
  5. custompurified by column chromatography (petroleum ether:ethyl acetate=1.5:1)

Quellen und Nachweise

ORD-Eintrag
ord-b202d7b9e66440a194eff6351137604b
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778939B2

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