Thiophene-3-carboxylic acid → HCID 16722644, Verbindung

HRID 2421113Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2421113
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.Cl.CN(C)CCCN=C=NCC.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([NH2:46])[CH:26]=[CH:27][C:28]=1[C:29]1[O:30][C:31]([C:34]2[C:35]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[N:36][O:37][C:38]=2[CH3:39])=[N:32][N:33]=1>ClCCl>[CH3:21][O:22][C:23]1[CH:24]=[C:25]([NH:46][C:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)=[O:8])[CH:26]=[CH:27][C:28]=1[C:29]1[O:30][C:31]([C:34]2[C:35]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[N:36][O:37][C:38]=2[CH3:39])=[N:32][N:33]=1

Komponenten

5

Edukt 3

HCID 6918Thiophene-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 167225873-Methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenylamine

Produkt 1

HCID 16722644HCID 16722644, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-thiophenecarboxylic acid (162 mg, 1.26 mmol) in dichloromethane (4 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (242 mg, 1.26 mmol). After stirring for 2 min 3-methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenylamine (400 mg, 1.15 mmol) was added and stirring was continued for 3 d at ambient temperature. The reaction mixture was extracted with aqueous HCl (1 M, 15 mL) and ethyl acetate (20 mL) and the aqueous layer was extracted with ethyl acetate (20 mL. Drying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=60:20:20 to 0:80:20) afforded the title compound (268 mg, 51%) as a white solid. MS: m/e=459.2 [M+H]+.

Aufarbeitung

  1. additionwas added
  2. extractionThe reaction mixture was extracted with aqueous HCl (1 M, 15 mL) and ethyl acetate (20 mL)
  3. extractionthe aqueous layer was extracted with ethyl acetate (20 mL
  4. dry with materialDrying over sodium sulfate, concentration and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=60:20:20 to 0:80:20)

Quellen und Nachweise

ORD-Eintrag
ord-a4178ee597a344da95bdb076e896002d
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07956074B2

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