1,2-Dichloroethane → Methyl (+/-)-7-[[bis[2-(4-pyridinyl)ethyl]amino]carbonyl]-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate

HRID 613354

Reaktionsgleichung

Reaktionsgleichung von HRID 613354
C(N(C(C)C)CC)(C)C.[N:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[CH:12][CH:11]=1.[C:27]([C:30]1[CH:31]=[CH:32][C:33]2[NH:39][CH:38]([CH2:40][C:41]([O:43][CH3:44])=[O:42])[C:37](=[O:45])[N:36]([CH3:46])[CH2:35][C:34]=2[CH:47]=1)(O)=[O:28].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.O.C([O-])(O)=O.[Na+]>CN(C=O)C>[N:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N:18]([CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)[C:27]([C:30]2[CH:31]=[CH:32][C:33]3[NH:39][CH:38]([CH2:40][C:41]([O:43][CH3:44])=[O:42])[C:37](=[O:45])[N:36]([CH3:46])[CH2:35][C:34]=3[CH:47]=2)=[O:28])=[CH:12][CH:11]=1

Komponenten

9

Edukt 7

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 416637Bis[2-(4-pyridyl)ethyl]amineHCID 516892Sodium BicarbonateHCID 23505570HCID 23505570, Verbindung

Produkt 1

HCID 53801004Methyl (+/-)-7-[[bis[2-(4-pyridinyl)ethyl]amino]carbonyl]-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Diisopropylethylamine (0.35 g, 2.7 mmole) was added in one portion to a stirred mixture of bis [2-(4-pyridyl)ethyl]amine (0.37 g, 1.65 mmole), methyl (±)-7-carboxy-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (0.44 g, 1.50 mmole), EDC (0.34 g, 1.8 mmole), and HOBT . H2O (0.24 g, 1.8 mmole) in DMF (8 mL) at 0° C. under argon, and the reaction was allowed to warm to RT. After 19.5 h, the reaction was poured into a mixture of ice water (100 g) and 5% NaHCO3 (10 mL) and extracted with CH2Cl2 (2×100 mL). The combined organic layers were washed with 5% NaHCO3 (50 mL), dried (MgSO4), and concentrated. Chromatography on silica gel (7% MeOH/CH2Cl2) gave the title compound (0.7 g, 88%). MS (ES) m/e 502.4 (M+H)+. c) (±)-7-[[Bis[2-(4-pyridinyl)ethyl]amino]carbonyl]-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetic acid

Aufarbeitung

  1. customat 0° C.
  2. extractionextracted with CH2Cl2 (2×100 mL)
  3. washThe combined organic layers were washed with 5% NaHCO3 (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-92fd1c0b6d984f06bc03d6daca9b551b
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06008214

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