Sodium Hydroxide → HCID 178525786, compound

HRID 931265Notes

Reaction equation

HRID 931265 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[NH:28][C:13]4=[N:14][C:15]([N:18]5[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([O:26]C)=[O:25])[CH2:19]5)=[CH:16][CH:17]=[C:12]4[N:11]=3)[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[NH:28][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][N:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501301HCID 178501301, compound

Product 1

HCID 178525786HCID 178525786, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (R)-methyl 1-(2-(2-cyclopropylpyrimidin-4-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylate (250 mg, 0.66 mmol) in ethanol (10 mL), was added an aqueous solution of sodium hydroxide (1N, 5 mL). The reaction mixture was stirred at room temperature for 2 h. The solvent was distilled off and the residue was partitioned between water and ethyl acetate. The aqueous layer was acidified with aqueous hydrochloric acid (10%) to pH˜2. The resulting precipitate was collected by filtration and dried under vacuum to afford (R)-1-(2-(2-cyclopropylpyrimidin-4-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylic acid (200 mg). MS (ES+APCI) (M+H) 365.2

Workup

  1. distillationThe solvent was distilled off
  2. customthe residue was partitioned between water and ethyl acetate
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-0d2086e35c5f46af80477352893fa30f
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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