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

HRID 1835155노트

반응식

HRID 1835155 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-01b903f348eb4822805d48b55299dab0
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06770646B2

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