Pyridine → HCID 131726135, compound

HRID 856922Notes

Reaction equation

HRID 856922 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([NH2:20])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].N1C=CC=CC=1.[CH3:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([Cl:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1>C(Cl)Cl>[ClH:37].[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([NH:20][S:34]([C:31]3[CH:32]=[CH:33][C:28]([CH3:27])=[CH:29][CH:30]=3)(=[O:36])=[O:35])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 21864784HCID 21864784, compound

Product 1

HCID 131726135HCID 131726135, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(4-isopropyl-1-piperazinyl)-1-naphthylamine (0.209 g, 0.776 mmol) (prepared according to Methods A and B) and pyridine (438 μL, 5.43 mmol) in CH2Cl2 (3.0 mL) was added 4-methylbenzenesulfonyl chloride (0.163 g, 0.850 mmol) in CH2Cl2 (1.0 mL). The solution was stirred at room temperature for 16 hours and the solid was collected by filtration as the HCl-salt to yield 0.236 g (66%); 1H NMR (DMSO-d6) δ 10.65 (br s, 1H), 9.95 (br s, 1H), 8.10–8.05 (m, 1H), 8.02–7.94 (m, 1H), 7.56–7.49 (m, 2H), 7.48–7.37 (m, 2H), 7.28–7.22 (m, 2H), 7.02–6.94 (m, 2H), 3.53–3.40 (m, 3H), 3.37–3.15 (m, 8H), 2.28 (s, 3H), 1.32–1.28 (m, 6H); MS (posES-FIA) m/z=423.1972 (M+H)(calc 423.1980).

Workup

  1. filtrationthe solid was collected by filtration as the HCl-salt
  2. customto yield 0.236 g (66%)

Sources & evidence

ORD record
ord-473b788746b34585a7eeed11c1ac83c0
Source dataset
uspto-grants-2006_12
Patent number
US07144883B2

Reaction notes

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