Tetrahydrofuran → 3-Methoxy-4-methyl-N-{4-(4-methyl-1-piperazinyl)-2-[(phenylsulfonyl)-amino]phenyl}benzenesulfonamide hydrochloride

HRID 2237656Notes

Reaction equation

HRID 2237656 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([N+:24]([O-])=O)=[C:12]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:13]=2)[CH2:4][CH2:3]1.O.NN.CO[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[CH:34][C:33]=1[S:39]([Cl:42])(=[O:41])=[O:40].C1C[O:46][CH2:45]C1>[Ni]>[ClH:42].[CH3:45][O:46][C:35]1[CH:34]=[C:33]([S:39]([NH:24][C:11]2[CH:10]=[CH:9][C:8]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:13][C:12]=2[NH:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])(=[O:40])=[O:41])[CH:32]=[CH:37][C:36]=1[CH3:38]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 11164762N-[5-(4-methyl-1-piperazinyl)-2-nitrophenyl]benzenesulfonamideHCID 113450482-Methoxy-4-methylbenzene-1-sulfonyl chloride

Product 1

HCID 222724583-Methoxy-4-methyl-N-{4-(4-methyl-1-piperazinyl)-2-[(phenylsulfonyl)-amino]phenyl}benzenesulfonamide hydrochlorideYield 28%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

N-[5-(4-Methyl-1-piperazinyl)-2-nitrophenyl]benzenesulfonamide (0.600 g, 1.59 mmol) was dissolved in THF (20 mL) followed by the addition of Raney-Ni (0.322 g, in ethanol) and hydrazine hydrate (0.100 g, 2.0 mmol). The reaction mixture was stirred for 1 h, filtered through Celite and concentrated. The residue was dissolved in pyridine (12 mL) and divided in 12 equal parts. To one part was added 2-methoxy-4-methyl-benzenesulfonylchloride (44 mg, 0.20 mmol). The reaction mixture was stirred overnight, poured into petroleum ether to form a precipitate that was collected by centrifugation. The precipitate was purified by purified by column chromatography (SiO2, CH2Cl2/MeOH 95:5 to 9:1). The pure product was dissolved in MeOH and treated with HCl/diethyl ether to give 21 mg, (28% yield). MS (posES-FIA) m/z=found: 530.1635; Calcd: 530.1658.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in pyridine (12 mL)
  4. stirringThe reaction mixture was stirred overnight
  5. customto form a precipitate that
  6. customwas collected by centrifugation
  7. customThe precipitate was purified
  8. customby purified by column chromatography (SiO2, CH2Cl2/MeOH 95:5 to 9:1)
  9. dissolutionThe pure product was dissolved in MeOH
  10. additiontreated with HCl/diethyl ether
  11. customto give 21 mg, (28% yield)

Sources & evidence

ORD record
ord-1dea1e1a75e441a396569c20d92fbc49
Source dataset
uspto-grants-2010_05
Patent number
US07718650B2

Reaction notes

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