Benzylamine → 4-(8-benzyl-7-oxo-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepin-5-yl)-benzonitrile

HRID 15419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 15419
[CH:1]([C:3]1[N:7]([CH:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[CH2:9][C:10]([O:12]C)=O)[CH:6]=[N:5][CH:4]=1)=O.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:22]([N:29]1[C:10](=[O:12])[CH2:9][CH:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[N:7]2[CH:6]=[N:5][CH:4]=[C:3]2[CH2:1]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 17975636Methyl 3-[5-formyl-imidazol-1-yl]-3-(4-cyano-phenyl)-propionate

Produkt 1

HCID 99974924-(8-benzyl-7-oxo-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepin-5-yl)-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of the title C compound, methyl 3-[5-formyl-imidazol-1-yl]-3-(4-cyano-phenyl)-propionate (0.22 g, 0.78 mmol) in DCE (5 mL) is added benzylamine (0.100 mL, 0.92 mmol) followed by sodium triacetoxyborohydride (0.49 g, 2.3 mmol). The reaction mixture is stirred at RT for 16 h, then partitioned between EtOAc and saturated aqueous sodium bicarbonate, and the organic solution is washed with brine, dried (anhydrous sodium sulfate) and concentrated. The residue is subjected to flash chromatography (silica) eluting with EtOAc:MeOH:NH4OH (90:10:1) to give 4-(8-benzyl-7-oxo-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepin-5-yl)-benzonitrile: m.p. 65° C.; e/z (ES) 343 (M+1, 100%).

Aufarbeitung

  1. custompartitioned between EtOAc and saturated aqueous sodium bicarbonate
  2. washthe organic solution is washed with brine
  3. dry with materialdried (anhydrous sodium sulfate)
  4. concentrationconcentrated
  5. washeluting with EtOAc:MeOH:NH4OH (90:10:1)

Quellen und Nachweise

ORD-Eintrag
ord-44960f5c65a6459b8a36e6bd3cfa7881
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732603B2

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