Citric Acid → HCID 178458725, compound

HRID 1644591Notes

Reaction equation

HRID 1644591 reaction equation
C(O[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:12]([CH3:14])[CH3:13])=[CH:7][C:6]=1[C:15]1[NH:28][C:18]2=[N:19][CH:20]=[C:21]([C:23]([O:25]CC)=[O:24])[CH:22]=[C:17]2[N:16]=1)(C)C.[OH-].[Na+].[C:31](O)(=O)[CH2:32][C:33]([CH2:38][C:39](O)=O)(C(O)=O)O.[CH2:44]([OH:46])[CH3:45]>>[CH2:44]([O:46][C:10]1[CH:5]=[C:6]([C:15]2[NH:28][C:18]3=[N:19][CH:20]=[C:21]([C:23]([OH:25])=[O:24])[CH:22]=[C:17]3[N:16]=2)[CH:7]=[C:8]([O:11][CH:12]([CH3:14])[CH3:13])[CH:9]=1)[C:45]1[CH:39]=[CH:38][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 4

HCID 311Citric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 178469701HCID 178469701, compound

Product 1

HCID 178458725HCID 178458725, compound

Procedure

A solution of ethyl 2-(2,5-diisopropoxyphenyl)-3H-imidazo[4,5-b]pyridine-6-carboxylate (40 mg) and 1N aqueous sodium hydroxide solution (1 ml) in ethanol (2 ml) was stirred at room temperature for 48 hr. The reaction mixture was adjusted with 1N citric acid to pH 4, and the precipitated crystals were collected by filtration and washed with water and ethanol to give the title compound (27 mg) as colorless crystals. purity 94%. M+H: 404. 1H NMR (DMSO-d6) δ: 1.32 (6H, d, J=6.0 Hz), 4.70-4.78 (1H,m), 5.21 (2H, s), 6.75 (1H, s), 7.32-7.53 (8H, m), 8.44 (1H, s), 8.92 (1H, s).

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washwashed with water and ethanol

Sources & evidence

ORD record
ord-69a33bc36afd498aba116c6ddee3363b
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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