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

HRID 449225Notes

Reaction equation

HRID 449225 reaction equation
[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

Participants

3

Reactant 1

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

Product 1

HCID 44425267HCID 44425267, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-[5-methyl-7-(3-nitro-phenyl)-benzo[1,2,4]triazin-3-ylamino]-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 the reaction 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).

Workup

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

Sources & evidence

ORD record
ord-c694c42999ba4845a0664c8ea788319c
Source dataset
uspto-grants-2013_07
Patent number
US08481536B2

Reaction notes

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