Piperidine → 2-Methyl-4-(3-methyl-1H-indazol-5-yl)-5-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitrile

HRID 408553

反応式

HRID 408553 の反応式
[C:1]1(=[O:7])[CH2:5][CH2:4][C:3](=O)[CH2:2]1.[CH3:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]=O)[CH:16]=2)[NH:11][N:10]=1.N1CCCCC1.[NH2:26][C:27]([CH3:31])=[CH:28][C:29]#[N:30]>C(O)C>[CH3:31][C:27]1[NH:26][C:3]2[CH2:4][CH2:5][C:1](=[O:7])[C:2]=2[CH:18]([C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[NH:11][N:10]=[C:9]3[CH3:8])[C:28]=1[C:29]#[N:30]

参加物

6

反応物 4

HCID 8082PiperidineHCID 706993-Amino-2-butenenitrileHCID 774661,3-CyclopentanedioneHCID 178434286HCID 178434286、化合物

生成物 1

HCID 1784284082-Methyl-4-(3-methyl-1H-indazol-5-yl)-5-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitrile

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

91 mg (0.936 mmol) cyclopentane-1,3-dione, 150 mg (0.936 mmol) 3-methyl-1H-indazole-5-carbaldehyde (Example 1A) and piperidine (0.1 ml) in ethanol (8 ml) were heated to reflux for 1.5 h and then left standing without stirring at room temperature overnight. The mixture was then evaporated to dryness, the remaining solid was dissolved in acetic acid (8 ml), and 77 mg (0.936 mmol) 3-aminobut-2-enenitrile were added. The solution was heated to reflux for 2 h. After cooling, the mixture was evaporated to dryness again, and the remaining solid was purified by preparative RP-HPLC (acetonitrile/water gradient) to yield 34 mg (12% of th.) of the title compound.

後処理

  1. temperatureto reflux for 1.5 h
  2. waitleft standing
  3. customThe mixture was then evaporated to dryness
  4. dissolutionthe remaining solid was dissolved in acetic acid (8 ml)
  5. temperatureThe solution was heated
  6. temperatureto reflux for 2 h
  7. temperatureAfter cooling
  8. customthe mixture was evaporated to dryness again
  9. customthe remaining solid was purified by preparative RP-HPLC (acetonitrile/water gradient)

出典と根拠

ORDレコード
ord-b93d4ba8a0d4431393c9f3b4ca172a6b
出典データセット
uspto-grants-2014_06
特許番号
US08759341B2

関連ノート

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