Sodium bis(trimethylsilyl)amide → HCID 10604585, Verbindung

HRID 343124Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 343124
[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][CH:29]=2)[C:4](=[O:34])[CH2:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:46][C:47]1[C:55]2[CH2:54][CH2:53][CH2:52][CH2:51][C:50]=2[N:49]([CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[N:48]=1>CN(C=O)C.C1COCC1>[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:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:4](=[O:34])[CH:3]1[CH2:46][C:47]1[C:55]2[CH2:54][CH2:53][CH2:52][CH2:51][C:50]=2[N:49]([CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[N:48]=1

Komponenten

6

Edukt 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 10614502HCID 10614502, VerbindungHCID 107900232-(2,4-Dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl) acetamide

Produkt 1

HCID 10604585HCID 10604585, VerbindungAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirring solution of 164 mg (0.36 mmol) of 2-(2,4-Dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl) acetamide in 5 mL of DMF at 0° C. is added 0.430 mL (0.78 mmol, 1.2 equiv) of a 1.0M solution of NaN(TMS)2 in THF. The resulting solution is stirred 5 min, and a solution of 120 mg (0.39 mmol, 1.1 equiv.) of 3-Bromomethyl-4,5,6,7-tetrahydro-1-benzyl-1H-indazole in 2 mL of DMF is added. The resulting solution is stirred for 3 h at RT then quenched with 5 mL of H2O. The reaction mixture is poured into 50 mL of EtOAc and extracted with H2O (2×50 mL). The organic layer is separated, dried (MgSO4), and the solvents removed in vacuo. Purification by silica gel flash column chromatography using hexane/EtOAc 1/1 as eluent afforded 175 mg of the title compound as a white solid: mp 173°-176° C.; 1H NMR (CDCl3, 400 MHz) δ7.37-6.84 (m, 18H), 5.02 (s, 2H), 4.99 (m, 1H), 4.22 (s, br, 2H), 4.10 (dd, 1H, J=5.3, 8.7), 3.823 (s, 3H), 3.36 (dd, 1H, J=8.6, 15.6), 3.09 (dd, 1H, J=5.3, 15.6), 2.54-2.38 (m, 4H), 1.67 (m, 4H), 1.04 (d, 6H, J=6.6); low resolution MS (FAB)m/e 682 (MH+).

Aufarbeitung

  1. stirringThe resulting solution is stirred for 3 h at RT
  2. customthen quenched with 5 mL of H2O
  3. additionThe reaction mixture is poured into 50 mL of EtOAc
  4. extractionextracted with H2O (2×50 mL)
  5. customThe organic layer is separated
  6. dry with materialdried (MgSO4)
  7. customthe solvents removed in vacuo
  8. customPurification by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-07d1463e96884cb4973c055f6e1e8900
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859007

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