1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 178493459, Verbindung

HRID 2391933

Reaktionsgleichung

Reaktionsgleichung von HRID 2391933
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.[CH3:47][N:48]([CH3:53])[CH2:49][CH2:50][NH:51][CH3:52]>C(Cl)Cl.C(Cl)Cl.O>[CH3:47][N:48]([CH3:53])[CH2:49][CH2:50][N:51]([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)[CH3:52]

Komponenten

6

Edukt 3

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 5049666Sodium triacetoxyborohydrideHCID 178493464HCID 178493464, Verbindung

Produkt 1

HCID 178493459HCID 178493459, VerbindungAusbeute 59,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21908982Water methylene chlorideLösungsmittel

Versuchsvorschrift

Sodium triacetoxyborohydride (168 mg, 0.794 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 (125 mg, 0.265 mmol) (Example 179) and N,N,N′-trimethylethylenediamine (81 mg, 0.792 mmol, 3 equiv) in DCM (4 mL) at rt, under an argon atmosphere. The reaction mixture was stirred for 18 h at rt, diluted in DCM/H2O and extracted with DCM. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1) followed by trituration in Et2O to afford 88 mg of the title compound as a yellow solid: ES-MS: 558 [M+H]+; tR=3.14 min (System 1); TLC: Rf=0.05 (DCM/MeOH/NH3aq, 94:5:1).

Aufarbeitung

  1. extractionextracted with DCM
  2. washThe organic phase was washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1)

Quellen und Nachweise

ORD-Eintrag
ord-d721145b3fe54a07a13a4b3b47e4ea4c
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273882B2

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