Pyridine → HCID 131726138, compound

HRID 856926Notes

Reaction equation

HRID 856926 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)[CH:11]=[C:10]([NH2:18])[N:9]=2)[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[CH2:3][CH2:4][N:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[C:10]([NH:18][S:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:33])=[O:32])[N:9]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 2825624HCID 2825624, compound

Product 1

HCID 131726138HCID 131726138, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(4-methyl-1-piperazinyl)-3-isoquinolinylamine (commercially available; 0.26 g, 1.07 mmol) and pyridine (0.60 mL, 7.51 mmol) in CH2Cl2 (3.0 mL) was added benzenesulfonyl chloride (151 μL, 1.18 mmol) in CH2Cl2 (1 mL). The mixture was stirred at room temperature for 16 hours and left in the refrigerator for 24 hours. The precipitate was collected by filtration to give 0.255 g (57%) of the pure product as the HCl-salt: 1H NMR (DMSO-d6) δ 10.93 (s, 2H), 7.96–7.90 (m, 3H), 7.79–7.75 (m, 1H), 7.64–7.56 (m, 4H), 7.44–7.38 (m, 1H), 7.01 (s, 1 H9, 3.70–3.15 (m, partly obscured by solvent signal, 8H), 2.79 (s, 3H); MS (posEI-DIP) m/z 382 (M+).

Workup

  1. waitleft in the refrigerator for 24 hours
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-db6a91d82db84f129c6bfafcb0e5c9e3
Source dataset
uspto-grants-2006_12
Patent number
US07144883B2

Reaction notes

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