Hydrochloric Acid → (R)-1-(2-(6-cyclopropylpyridin-2-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylic acid

HRID 931246Notes

Reaction equation

HRID 931246 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[NH:29][C:13]4=[N:14][C:15]([N:18]5[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([O:26]CC)=[O:25])[CH2:19]5)=[CH:16][CH:17]=[C:12]4[N:11]=3)[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C>[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[NH:29][C:13]4=[N:14][C:15]([N:18]5[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([OH:26])=[O:25])[CH2:19]5)=[CH:16][CH:17]=[C:12]4[N:11]=3)[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178472505HCID 178472505, compound

Product 1

HCID 178525785(R)-1-(2-(6-cyclopropylpyridin-2-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylic acidYield 107.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (R)-ethyl 1-(2-(6-cyclopropylpyridin-2-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylate (150 mg, 0.383 mmol) in ethanol (15 mL) was added a 2N sodium hydroxide solution (5 mL) at 0° C. The mixture was stirred at room temperature for 2 h, then was neutralized with a 2M hydrochloric acid solution and was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford (R)-1-(2-(6-cyclopropylpyridin-2-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylic acid (150 mg). MS (ES+APCI) (M+H) 364.2; LCMS retention time 2.974 min (Method J).

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cfd91106b9d0478bbe7d4996a965d799
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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