Carbon Dioxide → 2,6-Dihydro-2-methyl-4-(2-methylpropyl)-6-phenylmethyl-1h-pyrrolo[3,4-d]pyridazin-1-one-5-carboxylic acid

HRID 1835155ノート

反応式

HRID 1835155 の反応式
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][N:14]1[C:19](=[O:20])[C:18]2=[CH:21][N:22]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:23]=[C:17]2[C:16]([CH2:31][CH:32]([CH3:34])[CH3:33])=[N:15]1.[C:35](=[O:37])=[O:36]>O1CCCC1>[CH3:13][N:14]1[C:19](=[O:20])[C:18]2=[CH:21][N:22]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:23]([C:35]([OH:37])=[O:36])=[C:17]2[C:16]([CH2:31][CH:32]([CH3:34])[CH3:33])=[N:15]1

参加物

6

反応物 4

HCID 280Carbon DioxideHCID 7912DiisopropylamineHCID 235032512,6-Dihydro-2-methyl-4-(2-methylpropyl)-6-phenylmethyl-1h-pyrrolo[3,4-d]pyridazin-1-oneHCID 178418339Butyllithium

生成物 1

HCID 235032362,6-Dihydro-2-methyl-4-(2-methylpropyl)-6-phenylmethyl-1h-pyrrolo[3,4-d]pyridazin-1-one-5-carboxylic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Butyl lithium (2.5M in hexanes, 2.35 m) was added dropwise to a stirred solution of diisopropylamine (0.85 ml) in dry tetrahydrofuran (10 ml) at 0° C., under nitrogen. The reaction was stirred at 0° C. for 30 minutes, then cooled to −78° C. To this was added a solution of 2,6-dihydro-2-methyl-4-(2-methylpropyl)-6-(1-phenylmethyl)-1H-pyrrolo[3,4-d]pyridazin-1-one (1.5 g, prepared as in Example 14 step b) in dry tetrahydrofuran (10 ml), and stirring was continued for 30 minutes. This anion was then added to an excess of solid carbon dioxide. The reaction was allowed to warm to room temperature overnight, and was then quenched by the addition of water. The mixture was extracted into ethyl acetate, washed with brine, dried and evaporated to give a yellow oil, which was chromatographed, eluting with ethyl acetate:isohexane(3:7), to give the sub-title compound as a yellow solid (0.91 g).

後処理

  1. temperaturecooled to −78° C
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. temperatureto warm to room temperature overnight
  5. customwas then quenched by the addition of water
  6. extractionThe mixture was extracted into ethyl acetate
  7. washwashed with brine
  8. customdried
  9. customevaporated
  10. customto give a yellow oil, which
  11. customwas chromatographed
  12. washeluting with ethyl acetate:isohexane(3:7)

出典と根拠

ORDレコード
ord-01b903f348eb4822805d48b55299dab0
出典データセット
uspto-grants-2004_08
特許番号
US06770646B2

反応ノート

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