Sodium Hydroxide → HCID 22181389, compound

HRID 1796498Notes

Reaction equation

HRID 1796498 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3=[N:10][CH:11]=[C:12]([C:14]([O:16]C)=[O:15])[CH:13]=[C:8]3[N:7]=[C:6]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[CH:21][CH:20]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1.CO>[CH:1]1([CH2:4][N:5]2[C:9]3=[N:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[CH:13]=[C:8]3[N:7]=[C:6]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[CH:21][CH:20]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22181352HCID 22181352, compound

Product 1

HCID 22181389HCID 22181389, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(cyclopropylmethyl)-2-(4-ethoxybenzyl)-3H-imidazo[4,5-b]pyridine-6-carboxylate (260 mg, 0.71 mmol) in THF/MeOH (1:1, 6 ml) was added 1 N NaOH (3 ml, 3 mmol). The reaction mixture was stirred at room temperature for 3 h, and concentrated in vacuo. The residue was dissolved in H2O (10 ml), and acidified by adding 1 N HCl solution to pH5. The solid was collected (230 mg), and the filtrate was extracted with EtOAc (2×50 ml). The extracts were dried over Na2SO4 and concentrated in vacuo to afford an additional crop of product (20 mg). The desired acid was produced in quantitative yield.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in H2O (10 ml)
  3. additionby adding 1 N HCl solution to pH5
  4. customThe solid was collected (230 mg)
  5. extractionthe filtrate was extracted with EtOAc (2×50 ml)
  6. dry with materialThe extracts were dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-736b0627216b4cd8a5f75931269d7519
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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