Methyl chloroformate → 3,3a,4,5-tetrahydro-3a-methoxycarbonyl-N-[4'-(trifluoromethyl)phenyl]-2H-benz[g]indazole-2-carboxamide

HRID 232721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 232721
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]([F:38])([F:37])[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([N:24]2[CH2:32][CH:31]3[C:26]([C:27]4[CH:36]=[CH:35][CH:34]=[CH:33][C:28]=4[CH2:29][CH2:30]3)=[N:25]2)=[O:23])=[CH:17][CH:16]=1.Cl[C:40]([O:42][CH3:43])=[O:41]>C1COCC1.CCCCCC>[CH3:43][O:42][C:40]([C:31]12[CH2:30][CH2:29][C:28]3[CH:33]=[CH:34][CH:35]=[CH:36][C:27]=3[C:26]1=[N:25][N:24]([C:22]([NH:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]([F:13])([F:37])[F:38])=[CH:20][CH:19]=1)=[O:23])[CH2:32]2)=[O:41]

Komponenten

7

Edukt 4

HCID 6586Methyl chloroformateHCID 7912DiisopropylamineHCID 233594673,3a,4,5-Tetrahydro-N-[4-(trifluoromethyl)phenyl]-2H-benz[g]indazole-2-carboxamideHCID 178418339Butyllithium

Produkt 1

HCID 189883493,3a,4,5-tetrahydro-3a-methoxycarbonyl-N-[4'-(trifluoromethyl)phenyl]-2H-benz[g]indazole-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 0.9 ml of diisopropylamine in 10 ml of THF, at -78° C., was added 2.3 ml of 2.5M n-butyl lithium in hexane and the mixture was stirred for 5 mins. To this solution was added a solution of 1.0 g of the title compound of Step A in 5 ml of THF. The reaction was warmed to 0° C., recooled to -78° C. and then 0.75 ml of methyl chloroformate was added. The reaction mixture was then stirred for 24 h, with gradual warming to room temperature, quenched with 0.5 ml of glacial acetic acid, and poured into a 5% solution of aqueous NaHCO3. The mixture was extracted with chloroform, dried over magnesium sulfate and concentrated. Chromatography on silica gel with 30% ethyl acetate hexane afforded 0.25 g of the title compound, m.p. 177° to 180° C.

Aufarbeitung

  1. customrecooled to -78° C.
  2. stirringThe reaction mixture was then stirred for 24 h
  3. temperaturewith gradual warming to room temperature
  4. customquenched with 0.5 ml of glacial acetic acid
  5. additionpoured into a 5% solution of aqueous NaHCO3
  6. extractionThe mixture was extracted with chloroform
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e5ea415d48054ca5aae5b4caae1d1dd0
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591764

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