Piperidine → 7-Amino-5-(2-chloro-phenyl)-pyrazolo[1,5-a]pyridine-4,6-dicarbonitrile

HRID 644936Notes

Reaction equation

HRID 644936 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]#[N:8])=[N:2]1.[Cl:9][C:10]1[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=1[CH:12]=[C:13]([C:16]#[N:17])[C:14]#[N:15].N1CCCCC1>CCO>[NH2:17][C:16]1[N:2]2[N:1]=[CH:5][CH:4]=[C:3]2[C:6]([C:7]#[N:8])=[C:12]([C:11]2[CH:18]=[CH:19][CH:20]=[CH:21][C:10]=2[Cl:9])[C:13]=1[C:14]#[N:15]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 176042-ChlorobenzylidenemalononitrileHCID 1785108482-(1H-Pyrazol-3-yl)acetonitrile

Product 1

HCID 166603877-Amino-5-(2-chloro-phenyl)-pyrazolo[1,5-a]pyridine-4,6-dicarbonitrileYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of (1H-Pyrazol-3-yl)-acetonitrile (1.56 g, 14.5 mM) from Preparative Example 3 Step C in absolute EtOH (73 mL) at 25° C. was added o-chlorobenzylidene malononitrile (2.74 g, 14.5 mM) and piperidine (0.14 mL, 1.45 mM). The mixture then refluxed for 1.75 hr. The solvent evaporated. Chromatography on silica gel (30×5 cm) with CH2Cl2 afforded 7-Amino-5-(2-chloro-phenyl)-pyrazolo[1,5-a]pyridine-4,6-dicarbonitrile (0.62 g, 15%). HRMS: m/z 293.0472 (M+), Calcd. C15H8N5Cl1: m/z 293.0468; δC (CDCl3) CH: 99.3, 127.6, 129.6, 130.8, 131.6, 145.5; C: 75.7, 86.9, 114.8, 115.1, 131.5, 133.8, 138.4, 145.6, 149.2.

Workup

  1. temperatureThe mixture then refluxed for 1.75 hr
  2. customThe solvent evaporated

Sources & evidence

ORD record
ord-35052661fee945b0bb5927d18e875efb
Source dataset
uspto-grants-2010_04
Patent number
US07700773B2

Reaction notes

Loading…