4-Chloro-7-methoxycinnoline → HCID 68617576, Verbindung

HRID 1893667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1893667
[C:1]([O:5][C:6]([NH:8][CH:9]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:10]([N:12]1[CH2:16][CH:15]([OH:17])[CH2:14][CH:13]1[C:18]([NH:20][C:21]1([C:26]([OH:28])=[O:27])[CH2:23][CH:22]1[CH2:24][CH3:25])=[O:19])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC([O-])(C)C.[K+].Cl[C:40]1[C:49]2[C:44](=[CH:45][C:46]([O:50][CH3:51])=[CH:47][CH:48]=2)[N:43]=[N:42][CH:41]=1>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][CH:9]([C:29]([CH3:31])([CH3:30])[CH3:32])[C:10]([N:12]1[CH2:16][CH:15]([O:17][C:40]2[C:49]3[C:44](=[CH:45][C:46]([O:50][CH3:51])=[CH:47][CH:48]=3)[N:43]=[N:42][CH:41]=2)[CH2:14][CH:13]1[C:18]([NH:20][C:21]1([C:26]([OH:28])=[O:27])[CH2:23][CH:22]1[CH2:24][CH3:25])=[O:19])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 3

HCID 219910214-Chloro-7-methoxycinnolineHCID 23665647Potassium tert-butoxideHCID 686163761-{[1-(2-tert-Butoxycarbonylamino-3,3-dimethylbutyryl)-4-hydroxypyrrolidine-2-carbonyl]-amino}-2-ethyl-cyclopropanecarboxylic acid

Produkt 1

HCID 68617576HCID 68617576, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 1-{[1-(2-tert-butoxycarbonylamino-3,3-dimethyl-butyryl)-4-hydroxy-pyrrolidine-2-carbonyl]-amino}-2-ethyl-cyclopropanecarboxylic acid (210 mmg, 0.46 mmol) at 0° C. (external temperature, ice bath) was added KOt-Bu (1 m in THF, 2.3 mL, 2.3 mmol, 5 equiv.) and 4-chloro-7-methoxy-cinnoline (95 mg, 0.49 mmol, 1.06 equiv.) in THF (3 mL). The reaction was stirred at 0° C. for 2.5 h and diluted with EtOAc. The solution was washed with aqueous HCl (1M), resulting a precipitation of the crude product. The organic layer was dried over Na2SO4 and combined with the precipitate. The crude product was purified by column chromatography (0→15% MeOH/CH2Cl2) to provide 1-{[1-(2-tert-butoxycarbonylamino-3,3-dimethyl-butyryl)-4-(7-methoxy-cinnolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-ethyl-cyclopropanecarboxylic acid (161 mg, 57%).

Aufarbeitung

  1. washThe solution was washed with aqueous HCl (1M)
  2. customresulting
  3. customa precipitation of the crude product
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customThe crude product was purified by column chromatography (0→15% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-eab50754a6f44ebb9afd4caa9feb927f
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513186B2

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