Triethylamine → HCID 178448747, Verbindung

HRID 1931135Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1931135
[C:1]([C:5]1[S:9][C:8](=[NH:10])[N:7]([CH2:11][CH2:12][CH2:13][CH3:14])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O.N1(O)C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:38][C:39]1[CH:40]=[CH:41][C:42]([F:48])=[C:43]([CH:47]=1)[C:44](O)=[O:45].C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:44](=[O:45])[C:43]2[CH:47]=[C:39]([Cl:38])[CH:40]=[CH:41][C:42]=2[F:48])/[N:7]([CH2:11][CH2:12][CH2:13][CH3:14])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

9

Edukt 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27365375-Chloro-2-fluorobenzoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 666433495-Tert-butyl-3-butyl-1,3,4-thiadiazol-2(3h)-imine

Produkt 1

HCID 178448747HCID 178448747, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a mixture of Example 162C (250 mg, 1.17 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (179 mg, 1.17 mmol), N1-((ethylimino)methylene)-N3, N3-dimethylpropane-1,3-diamine hydrochloride (225 mg, 1.17 mmol), 5-chloro-2-fluorobenzoic acid (205 mg, 1.17 mmol) in 8 mL of THF was added triethylamine (163 μL, 1.17 mmol). The mixture was heated at 70° C. for 12 hours then cooled to ambient temperature and diluted with ethyl acetate and aqueous NaHCO3. The organic extract was concentrated and the residue was purified by chromatography on SiO2 using an Analogix® Intelliflash280™ (Hex-EtOAc, 0 to 30% gradient) to give the title compound. LC/MS m/z 369 (M+H)+.

Aufarbeitung

  1. temperaturethen cooled to ambient temperature
  2. extractionThe organic extract
  3. concentrationwas concentrated
  4. customthe residue was purified by chromatography on SiO2 using an Analogix® Intelliflash280™ (Hex-EtOAc, 0 to 30% gradient)

Quellen und Nachweise

ORD-Eintrag
ord-1130e649ff3043118421c29995fee5a3
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188135B2

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