Hydrochloric Acid → HCID 13416940, compound

HRID 1172962Notes

Reaction equation

HRID 1172962 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[N:5]=[C:6]2[CH:11]=[N:10][CH:9]=[CH:8][N:7]2[C:12]=1[C:13]([O:15]CC)=[O:14].Cl>O>[CH3:3][C:4]1[N:5]=[C:6]2[CH:11]=[N:10][CH:9]=[CH:8][N:7]2[C:12]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13416932Ethyl 2-methylimidazo[1,2-a]pyrazine-3-carboxylate

Product 1

HCID 13416940HCID 13416940, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (1.754 g, 43.9 mmol) in water (25 ml) was added to crude ethyl 2-methylimidazo[1,2-a]pyrazine-3-carboxylate (4.5 g, 21.93 mmol). The reaction is exothermic and goes to completion in minutes without additional heating. The mixture was acidified with concentrated HCl to pH 5. The solution was injected onto a preparative C18 column and washed with water and then eluted with 20% CH3CN/water. The product fractions were combined and concentrate to yield 2-Methyl-imidazo[1,2-a]pyrazine-3-carboxylic acid (250 mg, 6%) as a tan solid. LCMS (Table 1, Method a) Rt=0.84 min, m/z 176.18 (M−H)−; 1H NMR (400 MHz, DMSO-d6) δ 9.12 (m, 2H), 8.12 (m, 1H), 2.66 (s, 3H).

Workup

  1. waitgoes to completion in minutes without additional heating
  2. washwashed with water
  3. washeluted with 20% CH3CN/water
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-13d49af7e08d42dea311cb27b0149243
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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