Stannous chloride dihydrate → [2-Amino-4-(benzyloxy)-5-methoxyphenyl][4-(4-quinazolinyl)piperazino]methanone

HRID 1876824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876824
[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=[CH:27][N:26]=3)[CH2:21][CH2:20]2)=[O:18])=[C:11]([N+:35]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.Cl[Sn]Cl>CO>[NH2:35][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]([O:15][CH3:16])=[CH:13][C:12]=1[C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]=[CH:27][N:26]=2)[CH2:21][CH2:20]1)=[O:18]

Komponenten

4

Edukt 2

HCID 61436Stannous chloride dihydrateHCID 66882459[4-(Benzyloxy)-5-methoxy-2-nitrophenyl][4-(4-quinazolinyl)piperazino]methanone

Produkt 1

HCID 24936159[2-Amino-4-(benzyloxy)-5-methoxyphenyl][4-(4-quinazolinyl)piperazino]methanoneAusbeute 119,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

[4-(Benzyloxy)-5-methoxy-2-nitrophenyl][4-(4-quinazolinyl)piperazino]methanone (600 mg, 1.2 mmol) was dissolved in methanol (10 mL), SnCl2.2H2O (810 mg, 3.6 mmol) was added and refluxed until the TLC indicated the completion of the reaction. The methanol was evaporated by vacuum and the aqueous layer was then adjusted to pH 8 with 10% NaHCO3 solution and extracted with ethyl acetate (2×30 mL). The combined organic phase was dried over Na2SO4 and evaporated under vacuum to afford the crude (450 mg, 95% yield). This was further purified by column chromatography using ethyl acetate:hexane (6:4) as a solvent system to obtain the pure product (8d) (672 mg, 80% yield). 1H NMR (CDCl3) δ 3.20-3.30 (m, 4H), 3.65-3.75 (m, 4H), 3.95 (s, 3H), 5.20 (s, 2H), 6.20 (s, broad NH2), 6.45-6.55, (t, 1H) 6.70 (s, 1H), 7.30-7.50 (m, 5H), 7.55-7.65 (t, 1H), 7.65 (s, 1H), 7.70-7.90, (m, 2H), 7.85-7.95, (m, 2H); FABMS: 470 (M+H)+.

Aufarbeitung

  1. temperaturerefluxed until the TLC
  2. customthe completion of the reaction
  3. customThe methanol was evaporated by vacuum
  4. extractionextracted with ethyl acetate (2×30 mL)
  5. dry with materialThe combined organic phase was dried over Na2SO4
  6. customevaporated under vacuum
  7. customto afford the crude (450 mg, 95% yield)
  8. customThis was further purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4d18c5f72d6a49058147e059b7b2f772
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309726B2

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