Citric Acid → HCID 178458526, compound

HRID 1644604Notes

Reaction equation

HRID 1644604 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:29][CH:30]([CH3:32])[CH3:31])=[C:13]([C:15]2[NH:28][C:18]3=[N:19][C:20]([CH2:23][C:24]([O:26]C)=[O:25])=[CH:21][CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:29][CH:30]([CH3:32])[CH3:31])=[C:13]([C:15]2[NH:28][C:18]3=[N:19][C:20]([CH2:23][C:24]([OH:26])=[O:25])=[CH:21][CH:22]=[C:17]3[N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 178499398HCID 178499398, compound

Product 1

HCID 178458526HCID 178458526, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl {2-[5-(benzyloxy)-2-isopropoxyphenyl]-3H-imidazo[4,5-b]pyridin-5-yl}acetate (25 mg) and 1N sodium hydroxide (0.5 ml) in methanol (5 ml) was stirred at room temperature for 18 hr. The reaction mixture was adjusted with 1N citric acid to pH 4, and the precipitated crystals were collected by filtration and washed with diethyl ether to give the title compound (14 mg, yield 51%) as colorless crystals. purity 96%. M+H: 418. 1H NMR (CD3OD) δ: 1.45 (6H, d, J=6.0 Hz), 4.06 (2H, s), 4.78-4.83 (1H, m), 5.16 (2H, s), 7.28-7.58 (8H, m), 7.84 (1H, d, J=2.8 Hz), 8.28 (1H, d, J=8.3 Hz).

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-a880174565424a6390ecac842979c354
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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