Pyridine → HCID 131726139, compound

HRID 856928Notes

Reaction equation

HRID 856928 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH2:18])=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH2:4][CH2:3]1.N1C=CC=CC=1.[C:25]1([S:31]([Cl:34])(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[ClH:34].[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:18][S:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:33])=[O:32])=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 21864862HCID 21864862, compound

Product 1

HCID 131726139HCID 131726139, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-(4-methyl-1-piperazinyl)-5-nitroquinoline (0.379 g, 1.39 mmol) in THF:EtOH 1:4 solvent system was added Raney-Ni (1.0 mL suspension in EtOH) followed by hydrazine hydrate (0.348 g, 6.95 mmol). The mixture was stirred vigorously at room temperature for 16 hours and then filtered through celite pretreated with water. The filtrate was concentrated, and the residue was purified by column chromatography (SiO2, CHCl3/MeOH/NH3 9:1:0.4%) to give 0.337 g of 8-(4-methyl-1-piperazinyl)-5-quinolinylamine. The amine was dissolved in CH2Cl2 (6.0 mL) and pyridine (0.785 mL, 9.73 mmol) and benzenesulfonyl chloride (0.178 mL, 1.39 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours and then washed with saturated aqueous NaHCO3. The organic phase was dried with Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (SiO2, CHCl3/MeOH/NH3 9:1:0.4%) to give 0.130 g of the free base which was converted to its HCl-salt: 1H NMR (DMSO-d6) δ; 11.09 (br s, 1H), 10.32 (s, 1H), 8.94–8.89 (m, 1H), 8.55–8.48 (m, 1H), 7.68–7.65 (m, 2H), 7.64–7.57 (m, 2H), 7.54–7.49 (m, 2H), 7.27–7.22 (m, 1H), 7.12–7.08 (m, 1H), 3.95–3.84 (m, 2H), 3.55–3.49 (m, 2H), 3.45–3.35 (m, 2H), 3.26–3.16 (m, 2H), 2.85–2.82 (m, 3); MS (posESI) m/z 383 (M+H).

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialThe organic phase was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (SiO2, CHCl3/MeOH/NH3 9:1:0.4%)

Sources & evidence

ORD record
ord-41249ce4938d4396a1d0f67445c37ed9
Source dataset
uspto-grants-2006_12
Patent number
US07144883B2

Reaction notes

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