2-(5-Chloro-7-aminoindolin-1-yl)benzamide → 4-Chloro-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepin-7-one

HRID 4050

Reaktionsgleichung

Reaktionsgleichung von HRID 4050
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9](N)[CH:10]=1)[N:7]([C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([NH2:16])=[O:15])[CH2:6][CH2:5]2>CO.ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]2[NH:16][C:14](=[O:15])[C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[N:7]3[CH2:6][CH2:5][C:4]([CH:3]=1)=[C:8]23

Komponenten

3

Edukt 1

HCID 138232702-(5-Chloro-7-aminoindolin-1-yl)benzamide

Produkt 1

HCID 138232714-Chloro-1,2-dihydrobenzo[c]pyrrolo[1,2,3-ef][1,5]benzodiazepin-7-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

2-(5-chloro-7-aminoindolin-1-yl)benzamide of Example 1c (28.7 g, 0.10 mole) was dissolved in methanol/dichloromethane (DCM) solution (1:9 v/v) at 35° C. Silica gel (510 gm) was added to absorb the starting material, then the solvent was removed as much as possible under vacuum (50° C., 25 mmHg pressure for 1 hr.) The reaction mixture was then heated at 145°-155° C. and mechanically stirred for 11/2 hours. The heating was stopped when the mixture started to turn brown. The combined material was placed onto a flash chromatography column (1 kg, silica gel 60, slurry packed with DCM), eluted with DCM (16 l) and 2% CH3OH in DCM (10 l). The fractions containing the desired product were pooled and concentrated to yield a solid, 16 gm, (59%), m.p. 252°-255° C.

Aufarbeitung

  1. additionSilica gel (510 gm) was added
  2. customto absorb the starting material
  3. customthe solvent was removed as much as possible under vacuum (50° C., 25 mmHg pressure for 1 hr.) The reaction mixture
  4. temperaturewas then heated at 145°-155° C.
  5. washeluted with DCM (16 l) and 2% CH3OH in DCM (10 l)
  6. additionThe fractions containing the desired product
  7. concentrationconcentrated
  8. customto yield a solid, 16 gm, (59%), m.p. 252°-255° C.

Quellen und Nachweise

ORD-Eintrag
ord-f89196dda9834a2ab9a49b6b2bc34888
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04723003

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