Cesium carbonate → 4-[7-(3-Methoxycarbonyl-propoxy)-6-methyl-quinolin-8-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 2063574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2063574
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[C:16]([OH:26])=[C:17]([CH3:25])[CH:18]=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[C:16]([O:26][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[C:17]([CH3:25])[CH:18]=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 107604Methyl 4-bromobutyrateHCID 1359972734-(7-Hydroxy-6-methylquinolin-8-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 593661754-[7-(3-Methoxycarbonyl-propoxy)-6-methyl-quinolin-8-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-(7-Hydroxy-6-methyl-quinolin-8-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (1.3 g, 3.8 mmol) and methyl 4-bromobutyrate (680 mg, 3.8 mmol) were dissolved in DMF (7.5 mL). To this solution was added Cs2CO3 (3.7 g, 11.3 mmol) and reaction was stirred at room temperature for 18 h. The reaction was diluted with CH2Cl2 and washed with H2O (4×50 mL), then brine. The organic was then dried over MgSO4, filtered, and concentrated to give the crude product.

Aufarbeitung

  1. additionTo this solution was added
  2. washwashed with H2O (4×50 mL)
  3. dry with materialThe organic was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-aa57fb01928f49baad3193b2c5c00536
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288373B2

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