(6-Bromo-3-nitro-quinolin-4-yl)-(1,3-dimethyl-1H-pyrazol-4-yl)-amine → 6-bromo-4-N-(1,3-dimethylpyrazol-4-yl)quinoline-3,4-diamine

HRID 445538

Reaktionsgleichung

Reaktionsgleichung von HRID 445538
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-])=O)=[C:5]2[NH:15][C:16]1[C:17]([CH3:22])=[N:18][N:19]([CH3:21])[CH:20]=1>CO.C1COCC1.[Ni]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([NH2:12])=[C:5]2[NH:15][C:16]1[C:17]([CH3:22])=[N:18][N:19]([CH3:21])[CH:20]=1

Komponenten

4

Edukt 1

HCID 59619997(6-Bromo-3-nitro-quinolin-4-yl)-(1,3-dimethyl-1H-pyrazol-4-yl)-amine

Produkt 1

HCID 596197086-bromo-4-N-(1,3-dimethylpyrazol-4-yl)quinoline-3,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

(6-Bromo-3-nitro-quinolin-4-yl)-(1,3-dimethyl-1H-pyrazol-4-yl)-amine (Stage A.3, 3.67 g 9.73 mmol) was shacked in MeOH/THF 1:1 (120 ml) under 1.1 bar H2 in presence of Raney nickel (1.50 g) as catalyst for 5 h at rt. The RM was filtered over celite, the catalyst was washed with MeOH/DCM and the solution was evaporated to dryness to give the title compound as a red solid (HPLC tR 2.44 min (Method A); M+H=334; M−H=332 MS-ES)

Aufarbeitung

  1. filtrationThe RM was filtered over celite
  2. washthe catalyst was washed with MeOH/DCM
  3. customthe solution was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f94f41768a844b2a89591e8ca7096f40
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476294B2

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