Hydrochloric Acid → 2-(2-Aminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide monohydrochloride

HRID 1984714Notes

Reaction equation

HRID 1984714 reaction equation
[ClH:1].C(OC([NH:9][C:10]1[CH:15]=[C:14]([CH2:16][S:17][C:18]2[C:23]([C:24]([NH:26][C:27]3[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[CH:28]=3)=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:13]=[CH:12][N:11]=1)=O)(C)(C)C.C(O)C>O1CCOCC1>[ClH:1].[NH2:9][C:10]1[CH:15]=[C:14]([CH2:16][S:17][C:18]2[C:23]([C:24]([NH:26][C:27]3[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[CH:28]=3)=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:13]=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 112482792-(2-tert-Butoxycarbonylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

Product 1

HCID 231510662-(2-Aminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide monohydrochlorideYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4 N hydrochloric acid in 1,4-dioxane (5.0 mL) was added to a solution of 2-(2-tert-butoxycarbonylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide (Compound No. 2-1, 420 mg, 0.90 mmol) in 1,4-dioxane (5.0 mL) at room temperature, and the mixture was stirred for 12 hours. Ethanol (6.0 mL) was added to the reaction mixture, and the precipitated solid was filtered off. The solid was dried under reduced pressure at 60° C. to give 320 mg of the target compound as a colorless crystal. (Yield 88%)

Workup

  1. filtrationthe precipitated solid was filtered off
  2. customThe solid was dried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-09b739c3cb624641a56c4e1dcf2776b5
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

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