Isopropyl iodide → HCID 53978012, Verbindung

HRID 442679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 442679
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][C:11](=[O:22])[NH:10][N:9]=2)=[CH:4][CH:3]=1.I[CH:24]([CH3:26])[CH3:25]>CN(C=O)C.CCOC(C)=O>[CH:24]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][C:11](=[O:22])[NH:10][N:9]=2)=[CH:4][CH:3]=1)([CH3:26])[CH3:25]

Komponenten

5

Edukt 2

HCID 6362Isopropyl iodideHCID 9839097HCID 9839097, Verbindung

Produkt 1

HCID 53978012HCID 53978012, VerbindungAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of 1-(4-aminophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (110 mg, 0.373 mmol) in DMF (3 mL) was added 2-iodopropane (290 μL, 2.91 mmol). The mixture was stirred at 65° C. for two days, diluted with EtOAc (45 mL), washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography to afford the title compound as a tan solid (60 mg, 0.18 mmol, 48%), mp: 144°-146° C. 1H NMR (CDCl3) 8.20 (s, 1H), 7.41 (d, J=8.5, 2H), 6.81 (s, 1H), 6.74 (s, 1H), 6.56 (d, J=8.5, 2H), 6.02 (s, 2H), 3.80 (s, 1H), 3.69 (m, 1H), 3.42 (s, 2H), 1.24 (d, J=6.0, 6H).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a956b3b8b16c4cfaa2b2181483597404
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891871

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