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

HRID 489799Notes

Reaction equation

HRID 489799 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[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>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[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 222625966-amino-5-chloro-2-(methyloxy)-N-(4-piperidinylmethyl)-3-pyridinecarboxamideYield 85.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1,1-dimethylethyl 4-[({[6-amino-5-chloro-2-(methyloxy)-3-pyridinyl]carbonyl}amino)methyl]-1-piperidinecarboxylate (step 1 in example 1, 6.20 g, 15.5 mmol) in 10% methanolic hydrochloric acid (130 ml) was stirred at room temperature for 7 h. The mixture was concentrated to ca. 30 ml. The residue was basified with 2 N aqueous sodium hydroxide (pH=10) and the aqueous layer was extracted with dichloromethane (80 ml×3). The combined organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a column of aminopropyl silica gel eluting with methanol/dichloromethane (1:15) to give 3.94 g (85%) of the title compound as a white solid.

Workup

  1. concentrationThe mixture was concentrated to ca. 30 ml
  2. extractionthe aqueous layer was extracted with dichloromethane (80 ml×3)
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on a column of aminopropyl silica gel eluting with methanol/dichloromethane (1:15)

Sources & evidence

ORD record
ord-76e49326769347969e43401d50073238
Source dataset
uspto-grants-2005_12
Patent number
US06979690B2

Reaction notes

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