Citric Acid → HCID 178458531, compound

HRID 1644597Notes

Reaction equation

HRID 1644597 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:31][CH:32]([CH3:34])[CH3:33])=[C:13]([C:15]2[NH:30][C:18]3=[N:19][CH:20]=[C:21]([CH2:23][NH:24][CH2:25][C:26]([O:28]C)=[O:27])[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:31][CH:32]([CH3:34])[CH3:33])=[C:13]([C:15]2[NH:30][C:18]3=[N:19][CH:20]=[C:21]([CH2:23][NH:24][CH2:25][C:26]([OH:28])=[O:27])[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 178501585HCID 178501585, compound

Product 1

HCID 178458531HCID 178458531, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl N-({2-[5-(benzyloxy)-2-isopropoxyphenyl]-3H-imidazo[4,5-b]pyridin-6-yl}methyl)glycinate (15 mg) and 1N aqueous sodium hydroxide solution (0.1 ml) in methanol (2 ml) was stirred at room temperature for 18 hr. The reaction mixture was adjusted with 1N aqueous citric acid solution to pH 4. The precipitated crystals were collected by filtration and washed with diethyl ether to give the title compound (9.7 mg, yield 66%) as colorless crystals. melting point 182-184° C. purity 86%. M+H: 447. 1H NMR (DMSO-d6) δ: 1.48 (6H, d, J=6.0 Hz), 3.46 (2H, s), 3.98 (2H, s), 4.72-4.80 (1H, m), 5.17 (2H, s), 6.99-7.12 (2H, m), 7.29-7.51 (5H, m), 8.05 (1H, s), 8.19 (1H, s), 8.34 (1H, s).

Workup

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

Sources & evidence

ORD record
ord-00b21e84d34846aeb9a08fc37a127684
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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