Pyridine → HCID 69186030, compound

HRID 2373236Notes

Reaction equation

HRID 2373236 reaction equation
[C:1]([CH2:9][C:10]#[N:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:12]1[CH2:17][CH2:16][CH:15]([CH:18]=O)[CH2:14][CH2:13]1.[NH2:20][C:21]1[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=1.N1C=CC=C[CH:28]=1>>[CH2:26]([N:25]1[C:21]2=[N:20][C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:9]([C:10]#[N:11])[C:18]([CH:15]3[CH2:16][CH2:17][O:12][CH2:13][CH2:14]3)=[C:22]2[CH:23]=[N:24]1)[CH3:28]

Participants

5

Reactant 4

HCID 1049PyridineHCID 64799BenzoylacetonitrileHCID 1369272-Methyl-2H-pyrazol-3-ylamineHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehyde

Product 1

HCID 69186030HCID 69186030, compound

Conditions

Temperature
110 °C

Procedure

A mixture of benzoylacetonitrile (365 mg), tetrahydropyran-4-carbaldehyde (287 mg), 5-amino-1-methylpyrazole (289 mg) in pyridine (7.3 ml) was stirred for 2 days at 110° C. The solvent was removed under reduced pressure. The residue was purified with silica gel column chromatography to give pure 1-ethyl-6-phenyl-4-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (359 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-264c8cd5123f4ec0a05a9b408c9dc4ab
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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