Pyridine → HCID 131726131, compound

HRID 856919Notes

Reaction equation

HRID 856919 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH2:18])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.N1C=CC=CC=1.[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([Cl:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1>C(Cl)Cl>[ClH:35].[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:18][C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:9][CH:10]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 21864829HCID 21864829, compound

Product 1

HCID 131726131HCID 131726131, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(4-methyl-1-piperazinyl)-1-naphthylamine (prepared according to methods A and B) (0.099 g, 0.409 mmol) and pyridine (231 μL, 2.86 mmol) in CH2Cl2 (3.0 mL) was added 4-methylbenzenesulfonyl chloride (0.078 g, 0.409 mmol) in CH2Cl2 (1.0 mL). The solution was stirred at room temperature for 16 hours and then washed with saturated aqueous NaHCO3, dried with Na2SO4, filtered and concentrated. The crude product was purified via column chromatography (SiO2, CHCl3→CHCl3/MeOH/NH3 9:1:0.4%) to give the pure base which was converted to its HCl-salt: yield 110 mg (62%); 1H NMR (DMSO-d6) δ 10.86 (br s, 1H), 10.02 (s, 1H), 8.11–8.03 (m, 2H), 7.60–7.56 (m, 2H), 7.55–7.44 (m, 2H), 7.33–7.30 (m, 2H), 7.09–7.06 (m, 1H), 7.04–7.01 (m, 1H), 3.55–3.32 (m, 6H), 3.19–3.10 (m, 2H), 2.86 (s, 3H), 2.34 (s, 3H); MS (posES-FIA) m/z=395.1665 (M+H)(calc 395.1667).

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified via column chromatography (SiO2, CHCl3→CHCl3/MeOH/NH3 9:1:0.4%)
  6. customto give the pure base which

Sources & evidence

ORD record
ord-7fb0b9d5391d4bbb97f3dacefb20f653
Source dataset
uspto-grants-2006_12
Patent number
US07144883B2

Reaction notes

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