Hydrogen Bromide → 5-Chloroimidazo[1,2-A]pyrazine

HRID 80249

反応式

HRID 80249 の反応式
C([O-])(O)=O.[Na+].Br[CH2:7][CH:8](OC)OC.Br.[Cl:14][C:15]1[N:20]=[C:19]([NH2:21])[CH:18]=[N:17][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>O.CCCCCC.C(OC(=O)C)C.CC(O)C>[Cl:14][C:15]1[N:20]2[CH:7]=[CH:8][N:21]=[C:19]2[CH:18]=[N:17][CH:16]=1

参加物

10

反応物 5

HCID 260Hydrogen BromideHCID 10340Sodium CarbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 1184582-Amino-6-ChloropyrazineHCID 516892Sodium Bicarbonate

生成物 1

HCID 128415885-Chloroimidazo[1,2-A]pyrazine収率 25.31%

試薬・触媒・溶媒 4

HCID 962Water触媒HCID 3776Isopropanol溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

NaHCO3 (4.215 g, 50.1736 mmol) and IPA (40 mL) were added to a mixture of 2-bromo-1,1-dimethoxy-ethane (6.37 mL, 10.8066 mmol), 40% HBr (475 mL, 2.3157 mmol) and 2 drops of water previously refluxed for 1 hr. The reaction mixture was stirred for 5 mins and filtered. To the filtrate was added 6-chloro-pyrazin-2-ylamine (1 g, 7.7190 mmol) and the resulting mixture was refluxed for overnight. The reaction was monitored by TLC (50% ethylacetate in hexane). The reaction mixture was neutralized with Na2CO3 and partitioned between ethylacetate and water. The organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (1-2% MeOH in CHCl3) afforded 300 mg of the product (25.31% yield).

後処理

  1. temperaturepreviously refluxed for 1 hr
  2. filtrationfiltered
  3. temperaturethe resulting mixture was refluxed for overnight
  4. custompartitioned between ethylacetate and water
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customPurification by column chromatography on silica gel (1-2% MeOH in CHCl3)

出典と根拠

ORDレコード
ord-fe65c3a1d8c0408b94f2bf59208ad84f
出典データセット
uspto-grants-2014_09
特許番号
USRE045173E1

関連ノート

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