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Triethylamine → N-[2,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-1H-2-indolecarboxamide

HRID 482473
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 482473
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH3:17])=[CH:11][C:10]=2[O:18][CH3:19])[C:6]2[CH:20]=[CH:21][CH:22]=[CH:23][C:5]=2[N:4]([CH3:24])[C:3]1=[O:25].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH:53]1[C:61]2[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH:55]=[C:54]1[C:62](O)=[O:63].C(N(CC)CC)C>CN(C)C=O.O>[CH3:19][O:18][C:10]1[CH:11]=[C:12]([CH3:17])[CH:13]=[C:14]([O:15][CH3:16])[C:9]=1[C:7]1[C:6]2[CH:20]=[CH:21][CH:22]=[CH:23][C:5]=2[N:4]([CH3:24])[C:3](=[O:25])[CH:2]([NH:1][C:62]([C:54]2[NH:53][C:61]3[C:56]([CH:55]=2)=[CH:57][CH:58]=[CH:59][CH:60]=3)=[O:63])[N:8]=1
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Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 72899Indole-2-carboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 153796223-Amino-1,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-1,4-benzodiazepin-2-one

Produkt 1

HCID 9805268
N-[2,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-1H-2-indolecarboxamide
Ausbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 0.38 g of the laevorotatory enantiomer of 3-amino-1,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-1,4-benzodiazepin-2-one in 10 ml of dimethylformamide, cooled to 50° C., are added 0.52 g of BOP and 0.19 g of indole-2-carboxylic acid, followed by 0.23 ml of triethylamine. The reaction mixture is stirred overnight at room temperature and is then poured into water and extracted with ethyl acetate, dried over sodium sulphate and evaporated to dryness. The product is purified by chromatography on a column of silica gel (eluent: dichlormethane/methanol: 95/5). The fractions of pure product are evaporated to dryness and the residue is crystallized from isopropyl ether. White crystals of (-)-N-[2,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-1H-indol-2-carboxamide are obtained, melting at 135° C.; Yield=81%; [α]D20 =-408 (c=0.35 in 1N HCl/CH3OH-50/50).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulphate
  3. customevaporated to dryness
  4. customThe product is purified by chromatography on a column of silica gel (eluent: dichlormethane/methanol: 95/5)
  5. customThe fractions of pure product are evaporated to dryness
  6. customthe residue is crystallized from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-af3784b1032c459ba481c9d81961a642
Quelldatensatz
uspto-grants-1998_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05798353

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