4-[7-(2-chloro-5-nitro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide → 4-(7-(5-amino-2-chlorophenyl)-5-methylbenzo[e][1,2,4]triazin-3-ylamino)-N-(2-(pyrrolidin-1-yl)ethyl)benzenesulfonamide

HRID 273511Notes

Reaction equation

HRID 273511 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[CH:38]=[C:37]([CH3:39])[C:14]2[N:15]=[C:16]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([S:26]([NH:29][CH2:30][CH2:31][N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)(=[O:28])=[O:27])=[CH:22][CH:21]=3)[N:17]=[N:18][C:13]=2[CH:12]=1>CO>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:11]2[CH:38]=[C:37]([CH3:39])[C:14]3[N:15]=[C:16]([NH:19][C:20]4[CH:21]=[CH:22][C:23]([S:26]([NH:29][CH2:30][CH2:31][N:32]5[CH2:36][CH2:35][CH2:34][CH2:33]5)(=[O:27])=[O:28])=[CH:24][CH:25]=4)[N:17]=[N:18][C:13]=3[CH:12]=2)[CH:4]=1

Participants

3

Reactant 1

HCID 598377334-[7-(2-chloro-5-nitro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide

Product 1

HCID 444252664-(7-(5-amino-2-chlorophenyl)-5-methylbenzo[e][1,2,4]triazin-3-ylamino)-N-(2-(pyrrolidin-1-yl)ethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-[7-(2-chloro-5-nitro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide (0.41 mmol, 1.0 equiv) was dissolved in 20 mL of MeOH, and the reaction was evacuated of air by vacuum and placed under a blanket of argon. Pd/C (10% by wt) was added to the reaction, followed by another evacuation of argon, and by blanketing with hydrogen. The reaction was stirred under hydrogen blanket for 4 h, filtered through Celite, and concentrated by reduced pressure to give a crude residue, which was precipitated using EtOAc/hexanes (1:5 v/v) to give 4-[7-(5-amino-2-chloro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamino]-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide, as a dark green solid (89.4 mg, 41% yield). 1H NMR (DMSO-d6): δ 1.61 (m,4H), 2.34 (m, 4H), 2.42 (t, J=6.9 Hz, 2H), 2.71 (s, 3H), 2.85 (t, J=7.1 Hz, 2H), 5.43 (s, 1H), 6.65 (dd, J=8.7 Hz, J=2.8 Hz, 1H), 6.73 (d, J=2.7 Hz,1H), 7.21 (d, J=8.7 Hz, 1H), 7.83 (d, J=8.9 Hz, 2H), 7.89 (s, 1H), 8.15 (s, 1H), 8.21 (d, J=8.8 Hz, 2H). MS (ES+) m/z=538, LC retention time 2.13 min.

Workup

  1. customthe reaction was evacuated of air by vacuum
  2. additionPd/C (10% by wt) was added to the reaction
  3. filtrationfiltered through Celite
  4. concentrationconcentrated by reduced pressure
  5. customto give a crude residue, which
  6. customwas precipitated

Sources & evidence

ORD record
ord-2c44debd8d0449309746fb8516f4cc76
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Reaction notes

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