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

HRID 408554

反応式

HRID 408554 の反応式
[C:1]1(=[O:7])[CH2:5][CH2:4][C:3](=O)[CH2:2]1.[NH:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]=O)=[CH:14][CH:15]=2)[CH:10]=[N:9]1.N1CCCCC1.[NH2:25][C:26]([CH3:30])=[CH:27][C:28]#[N:29]>C(O)C>[NH:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17]3[C:27]([C:28]#[N:29])=[C:26]([CH3:30])[NH:25][C:3]4[CH2:4][CH2:5][C:1](=[O:7])[C:2]3=4)=[CH:14][CH:15]=2)[CH:10]=[N:9]1

参加物

6

反応物 4

HCID 8082PiperidineHCID 706993-Amino-2-butenenitrileHCID 774661,3-CyclopentanedioneHCID 212506441H-Indazole-5-carboxaldehyde

生成物 1

HCID 469113194-(1H-Indazol-5-yl)-2-methyl-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

100 mg (1.026 mmol) cyclopentane-1,3-dione, 150 mg (1.026 mmol) 1H-indazole-5-carbaldehyde and piperidine (0.1 ml) in ethanol (8 ml) were heated to reflux for 4 h. The mixture was then evaporated to dryness, the remaining solid was dissolved in acetic acid (8 ml), and 84 mg (1.026 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 40 mg (13% of th.) of the title compound.

後処理

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

出典と根拠

ORDレコード
ord-85102133bed04a03b8ccf8bcb8679c11
出典データセット
uspto-grants-2014_06
特許番号
US08759341B2

関連ノート

読み込み中…