Acetonitrile → 1,3-Dihydro-3-(RS)-(2-indolecarbonyloxy)-5-phenyl-2H-1,4-benzodiazepin-2-one

HRID 1084532

Reaktionsgleichung

Reaktionsgleichung von HRID 1084532
[OH:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[NH:4][C:3]1=[O:19].[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1[C:29](Cl)=[O:30].CC#N>C(Cl)Cl.CN(C)C1C=CN=CC=1>[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1[C:29]([O:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[NH:4][C:3]1=[O:19])=[O:30]

Komponenten

6

Edukt 3

HCID 6342AcetonitrileHCID 6140013-Hydroxy-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-oneHCID 118162081H-indole-2-carbonyl Chloride2×

Produkt 1

HCID 156147561,3-Dihydro-3-(RS)-(2-indolecarbonyloxy)-5-phenyl-2H-1,4-benzodiazepin-2-oneAusbeute 63,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1,3-Dihydro-3-(RS)-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one (100 mg, 0.398 mmol) was dissolved in CH2Cl2 (10 ml), treated with indole-2-carbonyl chloride (78.6 mg, 0.438 mmol) and 4-dimethylaminopyridine (DMAP, 53.5 mg, 0.438 mmol) and stirred 16 hrs. at 25° C. A second portion of indole-2-carbonylchloride (78.6 mg, 0.438 mmol and DMAP (53.5 mg, 0.438 mmol) was added and the reaction stirred an additional 24 hrs. Chromatography of the reaction mixture on silica gel (1% MeOH in CH2Cl2) gave the title compound (100 mg) as a white solid from MeCN: (m.p. 271°-273°).

Aufarbeitung

  1. customat 25° C
  2. stirringthe reaction stirred an additional 24 hrs

Quellen und Nachweise

ORD-Eintrag
ord-519bdb8277144676b03862c4140388cd
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05004741

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