Trifluoroacetic acid → (3S)-6-Chloro-3-methyl-4-(3-methyl-2-butenyl)-3,4-dihydro-1,4,5-triazanaphthalen-2(1H)-one

HRID 21531

Reaktionsgleichung

Reaktionsgleichung von HRID 21531
[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C@H:6]([CH3:13])[NH:5]2.[CH3:14][C:15]([CH3:19])=[CH:16][CH:17]=O.FC(F)(F)C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C@H:6]([CH3:13])[N:5]2[CH2:17][CH:16]=[C:15]([CH3:19])[CH3:14]

Komponenten

7

Edukt 5

HCID 6422Trifluoroacetic acidHCID 610203-Methyl-2-butenalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 57066600(3S)-6-Chloro-3-methyl-3,4-dihydro-1,4,5-triazanaphthalen-2(1H)-one

Produkt 1

HCID 57151233(3S)-6-Chloro-3-methyl-4-(3-methyl-2-butenyl)-3,4-dihydro-1,4,5-triazanaphthalen-2(1H)-oneAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

The compound of Example 2 (988 mg, 5.0 mmol) was suspended in 40 ml of anhydrous 1,2-dichloroethane. While stirring, 840 mg (10 mmol) of 3,3-dimethylacrolein and subsequently 1.9 ml (25 mmol) of trifluoroacetic acid were added. The mixture was cooled in an ice bath, 2.1 g (10 mmol) of sodium triacetoxyborohydride were introduced in portions, and the mixture was stirred at 0° C. for 1 h and at room temperature for a further 3 h. The reaction mixture was then added to about 150 ml of saturated aqueous sodium bicarbonate solution, the phases were separated, the aqueous was back-extracted three times with dichloromethane, and the combined organic extracts were dried (sodium sulfate) and concentrated. Chromatography on silica gel (ethyl acetate/heptane=1:2) provided 650 mg (49%) of the desired compound as a crystalline solid of melting point 136°-137° C.

Aufarbeitung

  1. temperatureThe mixture was cooled in an ice bath
  2. stirringthe mixture was stirred at 0° C. for 1 h and at room temperature for a further 3 h
  3. customthe phases were separated
  4. extractionthe aqueous was back-extracted three times with dichloromethane
  5. dry with materialthe combined organic extracts were dried (sodium sulfate)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-eb7be199d04a4f4faf4631cc6766a0dd
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424311

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