Sodium hydride → tert-Butyl 4-[2-(6-methoxy-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)propyl]piperazine-1-carboxylate

HRID 1644402Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1644402
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[NH:8][C:7]=2[CH:13]=1.[H-].[Na+].CS(O[CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1)(=O)=O.C(OC(=O)NC1CCN(CCN2C3C(=CC=C(OC)C=3)C=CC2=O)CC1)(C)(C)C>ClCCl.CC(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[N:8]([CH:22]([CH3:21])[CH2:23][N:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]3)[C:7]=2[CH:13]=1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 132049526-methoxy-3,4-dihydro-2H-1,4-benzoxazin-3-one2×HCID 15540662tert-Butyl 4-(3-((methylsulfonyl)oxy)propyl)piperazine-1-carboxylate2×HCID 59371209tert-butyl {1-[2-(7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate

Produkt 1

HCID 86642636tert-Butyl 4-[2-(6-methoxy-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)propyl]piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21966342Isopropanol methylene chlorideLösungsmittel

Versuchsvorschrift

6-Methoxy-2H-1,4-benzoxazin-3(4H)-one (Intermediate 48, 440 mg, 2.5 mmol) was deprotonated with sodium hydride (125 mg, 60% in oil, 3.2 mmol) and alkylated with tert-butyl 4-{3-[(methylsulfonyl)oxy]propyl}piperazine-1-carboxylate (Intermediate 120, 2.5 mmol) as described for Intermediate 2. Chromatography on silica gel with dichloromethane/2-propanol (95:5) gave 1.25 g (quantitative) of the product as a yellow oil.

Quellen und Nachweise

ORD-Eintrag
ord-e14aa7c4b704455b92797eca797cab44
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124602B2

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