Sodium Hydroxide → 2-[4-({[(6-Amino-5-chloro-2-methoxypyridin-3-yl)carbonyl]amino}-methyl)piperidine-1-yl]hexanoic acid

HRID 489809Notes

Reaction equation

HRID 489809 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]([CH:20]([CH2:26][CH2:27][CH2:28][CH3:29])[C:21]([O:23]CC)=[O:22])[CH2:16][CH2:15]2)=[O:11])=[CH:4][C:3]=1[Cl:30].[OH-].[Na+]>CO>[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]([CH:20]([CH2:26][CH2:27][CH2:28][CH3:29])[C:21]([OH:23])=[O:22])[CH2:16][CH2:15]2)=[O:11])=[CH:4][C:3]=1[Cl:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22262611Ethyl 2-[4-({[(6-amino-5-chloro-2-methoxypyridin-3-yl)carbonyl]amino}methyl)piperidin-1-yl]hexanoate

Product 1

HCID 222626632-[4-({[(6-Amino-5-chloro-2-methoxypyridin-3-yl)carbonyl]amino}-methyl)piperidine-1-yl]hexanoic acidYield 94.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-[4-({[(6-amino-5-chloro-2-methoxypyridin-3-yl)carbonyl]amino}methyl)piperidin-1-yl]hexanoate (4.3 g, 9.75 mmol) in methanol (50 ml) was added 2N aqueous sodium hydroxide (9.8 ml, 19.5 mmol) and the mixture was refluxed for 12 h. After cooled to room temperature, concentrated in vacuo. The resultant solid was treated with 2N aqueous hydrochloric acid (19.5 ml) to afford white solid, which was collected by filtration, washed with water (50 ml) gave 3.8 g (94%) of the title compound as white powder.

Workup

  1. temperaturethe mixture was refluxed for 12 h
  2. concentrationconcentrated in vacuo
  3. additionThe resultant solid was treated with 2N aqueous hydrochloric acid (19.5 ml)
  4. customto afford white solid, which
  5. filtrationwas collected by filtration
  6. washwashed with water (50 ml)

Sources & evidence

ORD record
ord-1162bcaf758c4476afe44aab01359071
Source dataset
uspto-grants-2005_12
Patent number
US06979690B2

Reaction notes

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