1,1-Dimethylethyl 4-[({[6-amino-5-chloro-2-(methyloxy)-3-pyridinyl]carbonyl}amino)methyl]-1-piperidinecarboxylate → 6-amino-5-chloro-2-oxo-N-(4-piperidinylmethyl)-1,2-dihydro-3-pyridinecarboxamide dihydrochloride

HRID 489783Notes

Reaction equation

HRID 489783 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8]C)[C:5]([C:10]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]2)=[O:11])=[CH:4][C:3]=1[Cl:27]>Cl>[ClH:27].[ClH:27].[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:10]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[O:11])=[CH:4][C:3]=1[Cl:27]

Participants

3

Reactant 1

HCID 222626051,1-Dimethylethyl 4-[({[6-amino-5-chloro-2-(methyloxy)-3-pyridinyl]carbonyl}amino)methyl]-1-piperidinecarboxylate

Product 1

HCID 222626096-amino-5-chloro-2-oxo-N-(4-piperidinylmethyl)-1,2-dihydro-3-pyridinecarboxamide dihydrochlorideYield 262.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 1,1-dimethylethyl 4-[({[6-amino-5-chloro-2-(methyloxy)-3-pyridinyl]carbonyl}amino)methyl]-1-piperidinecarboxylate (step 1, 350 mg, 0.88 mmol) in aqueous 2 N hydrochloric acid (20 ml) was refluxed with stirring for 12 h. After cooling to room temperature, the solvent was removed in vacuo. The residue was crystallized from methanol/diisopropyl ether to give 275 mg (88%) of the title compound as a gray powder.

Workup

  1. temperaturewas refluxed
  2. customthe solvent was removed in vacuo
  3. customThe residue was crystallized from methanol/diisopropyl ether

Sources & evidence

ORD record
ord-c8275117e39c4880a80794ee4ecccd6d
Source dataset
uspto-grants-2005_12
Patent number
US06979690B2

Reaction notes

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