Propionyl chloride → HCID 57717542, Verbindung

HRID 1360538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360538
[NH2:1][C:2]([CH3:22])([CH3:21])[CH2:3][C:4]1[N:5]([CH2:18][CH2:19][CH3:20])[N:6]=[C:7]2[C:16]=1[C:15]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:9]=[C:8]2[NH2:17].[C:23](Cl)(=[O:26])[CH2:24][CH3:25]>>[NH2:17][C:8]1[C:7]2=[N:6][N:5]([CH2:18][CH2:19][CH3:20])[C:4]([CH2:3][C:2]([NH:1][C:23](=[O:26])[CH2:24][CH3:25])([CH3:21])[CH3:22])=[C:16]2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Komponenten

3

Edukt 2

HCID 62324Propionyl chlorideHCID 57717565HCID 57717565, Verbindung

Produkt 1

HCID 57717542HCID 57717542, VerbindungAusbeute 77,1 %

Versuchsvorschrift

Using the method of Example 68, 1-(2-amino-2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine (prepared as described in Example 64, 595 mg, 2.00 mmol) was reacted with propionyl chloride (463 mg, 5.00 mmol). The crude product was purified by IFC (silica gel eluting with a gradient of 15 to 25% CMA in chloroform) followed by recrystallization from ethyl acetate/hexanes to provide 545 mg of N-[2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)-1,1-dimethylethyl]propionamide as a white solid, mp 158-159° C. MS (APCI) m/z 354 (M+H)+; Anal. Calcd for C20H27N5O: C, 67.96; H, 7.70; N, 19.81. Found: C, 67.80; H, 8.08; N, 19.77

Aufarbeitung

  1. customThe crude product was purified by IFC (silica gel eluting with a gradient of 15 to 25% CMA in chloroform)
  2. customfollowed by recrystallization from ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-dea1e9031c2b406e9bddabf7a98f6345
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879849B2

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