Hydrochloric Acid → 2-Methylimidazo[1,2-a]pyrazine-3-carboxylic acid

HRID 1172962ノート

反応式

HRID 1172962 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 134169402-Methylimidazo[1,2-a]pyrazine-3-carboxylic acid収率 6.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-13d49af7e08d42dea311cb27b0149243
出典データセット
uspto-grants-2010_11
特許番号
US07834039B2

反応ノート

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