HCID 88293119, Verbindung → HCID 18929586, Verbindung

HRID 1599076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1599076
[O:1]=[C:2]1[N:8]([CH2:9][C:10]([N:12]([CH:21]([CH3:23])[CH3:22])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:11])[C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=2[N:5]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[C:4](=[O:34])[C:3]1=[N:35]NC1C=CC=CC=1>[Zn].C(O)(=O)C>[NH2:35][CH:3]1[C:2](=[O:1])[N:8]([CH2:9][C:10]([N:12]([CH:21]([CH3:23])[CH3:22])[C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[O:11])[C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=2[N:5]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[C:4]1=[O:34]

Komponenten

4

Edukt 1

HCID 88293119HCID 88293119, Verbindung

Produkt 1

HCID 18929586HCID 18929586, VerbindungAusbeute 69,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 2-[2,4-Dioxo-3(phenyl-hydrazono)-5-pyrdin-2-yl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (460 mg), zinc dust (430 mg) and acetic acid (5.6 ml) was stirred at rt for 3 h. The solids were removed by filtration through celite, the filtrate was concentrated in vacuo and the residue azeotroped with hexane. The residue was dissolved in ethyl acetate (50 ml) and washed with 2N aqueous sodium bicarbonate (2×30 ml), water, (30 ml), brine (30 ml), dried (MgSO4) and concentrated in vacuo to afford the crude product (270 mg) which was used without further purification. 1H NMR (300 MHz, CDCl3); 1.03 (d, J=7 Hz, 6H), 3.79 (s, 3H), 4.02 (d J=10 Hz, 1H), 4.40 (s, 1H), 4.42 (d, J=10 Hz, 1H), 5.0 (sept, J=7.1 Hz, 1H), 6.8-7.3 (m, 10H), 7.44 (d, J=8.0 Hz 1H), 7.68 (d, J=8.0 Hz, 1H), 7.80 (m, 1H), 8.42 (d, J=3.9 Hz, 1H). Tlc (10% MeOH, CH2Cl2) Rf=0.23.

Aufarbeitung

  1. customThe solids were removed by filtration through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe residue azeotroped with hexane
  4. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  5. washwashed with 2N aqueous sodium bicarbonate (2×30 ml), water, (30 ml), brine (30 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0dcdcc4a02e441ecb18e7064fffc7cfc
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05739129

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