Sodium Acetate Trihydrate → HCID 178508954, Verbindung

HRID 29793

Reaktionsgleichung

Reaktionsgleichung von HRID 29793
OC(C(F)(F)F)=O.[NH2:8][C:9]1[NH:13][C:12](=[C:14]2[C:27]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24](Br)[CH:25]=4)[NH:20][C:19]=3[C:18](=[O:29])[NH:17][CH2:16][CH2:15]2)[C:11](=[O:30])[N:10]=1.O.O.O.C([O-])(=O)C.[Na+]>CO.[Pd]>[NH2:8][C:9]1[NH:13][C:12](=[C:14]2[C:27]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][C:19]=3[C:18](=[O:29])[NH:17][CH2:16][CH2:15]2)[C:11](=[O:30])[N:10]=1

Komponenten

5

Edukt 2

HCID 23665404Sodium Acetate TrihydrateHCID 178508953HCID 178508953, Verbindung

Produkt 1

HCID 178508954HCID 178508954, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 5-(2-amino-5-oxo-3,5-dihydro-imidazol-4-ylidene)-7-bromo-3,4,5,10-tetrahydro-2H-azepino[3,4-b]indol-1-one TFA salt (13 mg, 0.027 mmol), in MeOH (5 mL) is added sodium acetate trihydrate (24 mg, 0.18 mmol) and 10% Pd/C (4.5 mg). It is stirred at room temperature under a hydrogen atmosphere overnight and then the catalyst is removed by filtration. The solution is concentrated and the residue is purified by HPLC (C18 column, eluted with CH3CN/H2O with 0.05% TFA) to give 5-(2-amino-5-oxo-3.5-dihydro-imidazol-4-ylidene)-3,4,5,10-tetrahydro-2H-azepino[3,4-b]indol-1-one; 1H NMR (DMSO-d6) δ 3.30-3.36 (m, 4H), 7.20 (t, 1H, J=7.6 Hz), 7.33 (t, 1H, J=7.2 Hz), 7.53 (t, 1H, J=7.6 Hz), 7.58 (d, 1H, J=7.2 Hz), 8.36 (t, 1H, J=2.4 Hz), 9.20 (bs, 1H), 10.37 (bs, 1H), 12.45 (s, 1H); m/z [M++1] 296.1.

Aufarbeitung

  1. customthe catalyst is removed by filtration
  2. concentrationThe solution is concentrated
  3. customthe residue is purified by HPLC (C18 column, eluted with CH3CN/H2O with 0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-8218cad762124bff826949bbe53bd0ff
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423031B2

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