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

반응식

HRID 408553 반응식
[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]

참가 물질

6

반응물 4

HCID 8082PiperidineHCID 706993-Amino-2-butenenitrileHCID 774661,3-CyclopentanedioneHCID 178434286HCID 178434286, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b93d4ba8a0d4431393c9f3b4ca172a6b
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759341B2

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