Hydrochloric Acid → HCID 178458529, compound

HRID 1644600Notes

Reaction equation

HRID 1644600 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:28][CH:29]([CH3:31])[CH3:30])=[C:13]([C:15]2[NH:27][C:18]3=[N:19][C:20]([C:23]([O:25]C)=[O:24])=[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+].Cl>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:28][CH:29]([CH3:31])[CH3:30])=[C:13]([C:15]2[NH:27][C:18]3=[N:19][C:20]([C:23]([OH:25])=[O:24])=[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 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178497319HCID 178497319, compound

Product 1

HCID 178458529HCID 178458529, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution (2 ml) of methyl 2-[5-(benzyloxy)-2-isopropoxyphenyl]-3H-imidazo[4,5-b]pyridine-5-carboxylate (35 mg) and 1N aqueous sodium hydroxide solution (0.2 ml) in methanol was stirred at room temperature for 18 hr. The reaction mixture was adjusted with 1N hydrochloric acid to pH 3, and the precipitated crystals were collected by filtration and washed with acetonitrile to give the title compound (22 mg, yield 64%) as colorless crystals. purity 98%. M+H: 404. 1H NMR (DMSO-d6) δ: 1.37 (6H, d, J=5.0 Hz), 4.67-4.72 (1H, m), 5.17 (2H, s), 7.16-7.52 (7H, m), 7.73-8.13 (3H, m).

Workup

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

Sources & evidence

ORD record
ord-24cbd4ef3dee454ea4d3d5303548a190
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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