Ethanamine, 2,2,2-trifluoro- → HCID 178493463, Verbindung

HRID 1189906

Reaktionsgleichung

Reaktionsgleichung von HRID 1189906
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:15]([C:17]1[N:18]=[C:19]([NH:22][C:23]([C:25]2[C:26]3[N:27]=[CH:28][CH:29]=[N:30][C:31]=3[C:32]([C:35]3[C:40]([Cl:41])=[C:39]([O:42][CH3:43])[CH:38]=[C:37]([O:44][CH3:45])[C:36]=3[Cl:46])=[CH:33][CH:34]=2)=[O:24])[NH:20][CH:21]=1)=O.[F:47][C:48]([F:52])([F:51])[CH2:49][NH2:50]>C(Cl)Cl>[F:47][C:48]([F:52])([F:51])[CH2:49][NH:50][CH2:15][C:17]1[N:18]=[C:19]([NH:22][C:23]([C:25]2[C:26]3[N:27]=[CH:28][CH:29]=[N:30][C:31]=3[C:32]([C:35]3[C:36]([Cl:46])=[C:37]([O:44][CH3:45])[CH:38]=[C:39]([O:42][CH3:43])[C:40]=3[Cl:41])=[CH:33][CH:34]=2)=[O:24])[NH:20][CH:21]=1

Komponenten

5

Edukt 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 5049666Sodium triacetoxyborohydrideHCID 178493464HCID 178493464, Verbindung

Produkt 1

HCID 178493463HCID 178493463, VerbindungAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Sodium triacetoxyborohydride (101 mg, 0.476 mmol, 3 equiv) was added to a suspension of 8-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid (4-formyl-1H-imidazol-2-yl)-amide (75 mg, 0.159 mmol) and trifluoroethylamine (15 μl, 0.188 mmol), 1.18 equiv) in DCM (3 mL) at rt, under an argon atmosphere. The reaction mixture was stirred for 18 h at rt, quenched by addition of H2O and extracted with DCM. The organic phase was washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 98:1:1) followed by trituration in Et2O to afford 55 mg of the title compound as a yellow solid: ES-MS: 555 [M+H]+; tR=3.78 min (System 1); TLC: Rf=0.55 (DCM/MeOH, 9:1).

Aufarbeitung

  1. customquenched by addition of H2O
  2. extractionextracted with DCM
  3. washThe organic phase was washed with a saturated aqueous solution of NaHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 98:1:1)

Quellen und Nachweise

ORD-Eintrag
ord-ddfb45cb8ad8457c977428d9c9050b0f
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674099B2

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