4-[5-methyl-7-(3-nitro-phenyl)-benzo[1,2,4]triazin-3-yl amino]-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide → HCID 44425267, Verbindung

HRID 273528

Reaktionsgleichung

Reaktionsgleichung von HRID 273528
[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH:22][CH2:23][CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)(=[O:21])=[O:20])=[CH:15][CH:14]=3)[N:10]=[N:11][C:6]=2[CH:5]=[C:4]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([N+:36]([O-])=O)[CH:31]=2)[CH:3]=1>[Pd]>[NH2:36][C:32]1[CH:31]=[C:30]([C:4]2[CH:3]=[C:2]([CH3:1])[C:7]3[N:8]=[C:9]([NH:12][C:13]4[CH:14]=[CH:15][C:16]([S:19]([NH:22][CH2:23][CH2:24][N:25]5[CH2:26][CH2:27][CH2:28][CH2:29]5)(=[O:20])=[O:21])=[CH:17][CH:18]=4)[N:10]=[N:11][C:6]=3[CH:5]=2)[CH:35]=[CH:34][CH:33]=1

Komponenten

3

Edukt 1

HCID 598376844-[5-methyl-7-(3-nitro-phenyl)-benzo[1,2,4]triazin-3-yl amino]-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide

Produkt 1

HCID 44425267HCID 44425267, VerbindungAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

4-[5-methyl-7-(3-nitro-phenyl)-benzo[1,2,4]triazin-3-yl amino]-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide (0.16 g, 0.3 mmol, 1 equiv) was combined with 10% palladium on carbon (0.135 g) and flushed with argon. The reactants were then diluted with methanol (15 mL), and rthe eaction atmosphere was evacuated and replaced with hydrogen. A hydrogen balloon was affixed and the reaction was allowed to stir for 3 hours. Argon was then bubbled through the reaction mixture and the contents were filtered though a pad of Celite. The solvents were evaporated to provide the product as an orange solid (0.15 g, 98% yield). MS (ESI+): m/z=504.6, LC retention time: 1.84 min. 1H NMR (DMSO-d6): δ 1.64 (bs, 4H), 2.72 (s, 3H), 2.87 (bs, 2H), 5.26 (s, 2H), 6.65 (d, J=7.8 Hz, 1H), 7.00 (d, J=8.1 Hz, 1H), 7.05 (m, 1H), 7.18 (t, J=7.8 Hz, 1H), 7.83 (d, J=8.8 Hz, 2H), 8.12 (s, 1H), 8.21 (d, J=8.8 Hz, 2H), 8.27 (d, J=1.7 Hz, 1H), 11.44 (s, 1H).

Aufarbeitung

  1. customflushed with argon
  2. additionThe reactants were then diluted with methanol (15 mL)
  3. customrthe eaction atmosphere was evacuated
  4. customArgon was then bubbled through the reaction mixture
  5. filtrationthe contents were filtered though a pad of Celite
  6. customThe solvents were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-18a5e4757cbd4f35bd1e14e23b7b8760
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456176B2

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