Pyridine → HCID 131726138, compound

HRID 2100332Notes

Reaction equation

HRID 2100332 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, 1H9, 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-75e5320492f846d8998c6721322a0683
Source dataset
uspto-grants-2009_08
Patent number
US07572787B2

Reaction notes

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