p-Toluenesulfonic acid → 5-Amino-n-[(1-butyl-4-piperidinyl)methyl]-6-chloro-2-propylimidazo[1,2-a]pyridine-8-carboxamide p-toluenesulfonate salt

HRID 1168257Notes

Reaction equation

HRID 1168257 reaction equation
[NH2:1][C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][CH2:12][CH3:13])[N:10]=[C:6]2[C:5]([C:14]([NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:19]2)=[O:15])=[CH:4][C:3]=1[Cl:28].[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35]([OH:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1>CO>[C:29]1([CH3:39])[CH:30]=[CH:31][C:32]([S:35]([OH:38])(=[O:36])=[O:37])=[CH:33][CH:34]=1.[NH2:1][C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][CH2:12][CH3:13])[N:10]=[C:6]2[C:5]([C:14]([NH:16][CH2:17][CH:18]2[CH2:19][CH2:20][N:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23]2)=[O:15])=[CH:4][C:3]=1[Cl:28]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 229922185-Amino-N-[(1-butyl-4-piperidinyl)methyl]-6-chloro-2-propylimidazo[1,2-a]pyridine-8-carboxamide

Product 1

HCID 229922175-Amino-n-[(1-butyl-4-piperidinyl)methyl]-6-chloro-2-propylimidazo[1,2-a]pyridine-8-carboxamide p-toluenesulfonate saltYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Amino-N-[(1-butyl-4-piperidinyl)methyl]-6-chloro-2-propylimidazo[1,2-a]pyridine-8-carboxamide (EXAMPLE 16, Step 3, 185 mg, 0.46 mmol) was treated with p-toluenesulfonic acid (86.6 mg, 0.46 mmol) in methanol, concentrated and washed with diethyl ether and hexane. 200 mg (76%) of the title compound was obtained.

Workup

  1. concentrationconcentrated
  2. washwashed with diethyl ether and hexane

Sources & evidence

ORD record
ord-8963994b41c14e4ebdd791c2e60a189b
Source dataset
uspto-grants-2003_09
Patent number
US06624162B2

Reaction notes

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