Chloride → Methyl 7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylate

HRID 1971072ノート

反応式

HRID 1971072 の反応式
[Cl-].Cl.[CH2:3]([N:10]([CH2:14][C:15]1[N:16]=[CH:17][NH:18][C:19]=1[C:20]([O:22][CH3:23])=[O:21])[CH2:11][CH2:12]Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(#N)C>[CH2:3]([N:10]1[CH2:11][CH2:12][N:16]2[CH:17]=[N:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:15]2[CH2:14]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

4

反応物 2

HCID 312ChlorideHCID 178499150HCID 178499150、化合物

生成物 1

HCID 57635262Methyl 7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-1-carboxylate収率 67.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

The chloride, Intermediate 1E (0.97 g, 3.15 mmol) was dissolved in acetonitrile (30 mL) and TEA (1.77 mL, 12.62 mmol) was added drop wise. The resulting mixture was stirred at 80° C. under nitrogen overnight. The mixture was allowed to cool, was filtered and the filtrate was concentrated. The residue was partitioned between DCM and saturated NaHCO3 solution and the phases were separated. The aqueous phase was further extracted with DCM and combined organic extracts were dried over anhydrous MgSO4, filtered and concentrated. The crude residue was purified using normal phase chromatography, eluting with a 0-40% methanol/DCM gradient to provide product Intermediate 1F (0.58 g, 66%) as a brown solid.

後処理

  1. temperatureto cool
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was partitioned between DCM and saturated NaHCO3 solution
  5. customthe phases were separated
  6. extractionThe aqueous phase was further extracted with DCM
  7. dry with materialwere dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude residue was purified
  11. washeluting with a 0-40% methanol/DCM gradient

出典と根拠

ORDレコード
ord-21083b836e0f41aeab8dadaa8345ed85
出典データセット
uspto-grants-2013_04
特許番号
US08431565B2

反応ノート

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