Piperidine → 7-Amino-5-phenyl-pyrazolo[1,5-a]pyridine-4,6-dicarbonitrile

HRID 644937

反応式

HRID 644937 の反応式
[NH:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]#[N:8])=[N:2]1.[CH:9](=[C:16]([C:19]#[N:20])[C:17]#[N:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1CCCCC1>CCO>[NH2:20][C:19]1[N:2]2[N:1]=[CH:5][CH:4]=[C:3]2[C:6]([C:7]#[N:8])=[C:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:16]=1[C:17]#[N:18]

参加物

5

反応物 3

HCID 8082PiperidineHCID 17608Malononitrile, benzylidene-HCID 1785108482-(1H-Pyrazol-3-yl)acetonitrile

生成物 1

HCID 592637927-Amino-5-phenyl-pyrazolo[1,5-a]pyridine-4,6-dicarbonitrile収率 14.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a stirred solution of (1H-Pyrazol-3-yl)-acetonitrile (100 mg, 0.93 mM) in absolute EtOH (4.7 mL) at 25° C. was added benzylidene malononitrile (144 mg, 0.93 mM) and piperidine (0.009 mL, 0.09 mM). The mixture then refluxed for 1.0 hr. The solvent evaporated. Chromatography done on silica gel (60×2.5 cm) with CH2Cl2 afforded 7-Amino-5-phenyl-pyrazolo[1,5-a]pyridine-4,6-dicarbonitrile (34.6 mg, 14%) LCMS: MH+=260; HRMS: m/z 260.0938 (MH+), Calcd. C15H9N5: m/z 260.0936; δC (DMSO) CH: 99.0, 128.5, 128.5, 128.8, 128.8, 129.8, 145.4; C: 75.4, 86.9, 115.5, 116.0, 134.8, 138.9, 148.1, 149.4.

後処理

  1. temperatureThe mixture then refluxed for 1.0 hr
  2. customThe solvent evaporated

出典と根拠

ORDレコード
ord-ef21a8f690a14c03a4fe82d6f8aec559
出典データセット
uspto-grants-2010_04
特許番号
US07700773B2

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