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

HRID 1984719Notes

Reaction equation

HRID 1984719 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][S:9][C:10]2[C:15]([C:16]([N:18]([CH2:27][C:28]([O:30]C(C)(C)C)=[O:29])[C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[CH:20]=3)=[O:17])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:4][N:3]=1.[ClH:35]>C(OCC)(=O)C>[ClH:35].[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][S:9][C:10]2[C:15]([C:16]([N:18]([CH2:27][C:28]([OH:30])=[O:29])[C:19]3[CH:20]=[C:21]([CH3:26])[CH:22]=[C:23]([CH3:25])[CH:24]=3)=[O:17])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 231508722-(2-Aminopyridin-4-ylmethylthio)-N-(tert-butoxycarbonylmethyl)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

Product 1

HCID 231510472-(2-Aminopyridin-4-ylmethylthio)-N-carboxymethyl-N-(3,5-dimethylphenyl)pyridine-3-carboxamide monohydrochlorideYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2-(2-Aminopyridin-4-ylmethylthio)-N-(tert-butoxycarbonylmethyl)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide (Compound No. 7-1, 40 mg, 0.084 mmol) was dissolved in ethyl acetate (1.0 mL), and 4 N hydrochloric acid in ethyl acetate (1.0 mL) was added thereto, and then the mixture was stirred for 18 hours at room temperature. The precipitated solid was filtered off with diethyl ether and dried under reduced pressure to give 30 mg of the target compound as a colorless solid. (Yield 86%)

Workup

  1. filtrationThe precipitated solid was filtered off with diethyl ether
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-9dd5ca8102bd45118f901efb272bbe02
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

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