HCID 10179024, compound → 5,6-Diamino-2-pyridinecarbonitrile

HRID 1784791Notes

Reaction equation

HRID 1784791 reaction equation
ClC1C=C(C=CC=1Cl)OC1C=CC(C2[NH:13][C:14]3[C:15]([N:23]=2)=[N:16][C:17]([C:20]([NH2:22])=O)=[CH:18][CH:19]=3)=CC=1.NC1N=C(C#N)C=CC=1[N+]([O-])=O>[Pd].C(O)C>[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:22])=[N:16][C:15]=1[NH2:23]

Participants

5

Reactant 2

HCID 10179024HCID 10179024, compoundHCID 52987934HCID 52987934, compound

Product 1

HCID 450795585,6-Diamino-2-pyridinecarbonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-[4-(3,4-Dichloro-phenoxy)-phenyl]-1H-imidazo[4,5-b]pyridine-5-carboxylic acid amide. A flask containing 6-amino-5-nitro-pyridine-2-carbonitrile (67 mg, 0.40 mmol), 10% palladium on carbon (catalytic) and ethanol (2.0 mL) was put under an atmosphere of H2 using a balloon. The mixture was stirred at room temperature for 3 h, and filtered through a pad of celite. The filtrate was concentrated to provide crude 5,6-diamino-pyridine-2-carbonitrile. A portion of this 5,6-diamino-pyridine-2-carbonitrile (89 mg, 0.66 mmol) was treated with 4-(3,4-dichloro-phenoxy)-benzaldehyde (177 mg, 0.66 mmol), Na2S2O5 (188 mg, 0.99 mmol) and N,N-dimethylacetamide (3.0 mL). The mixture was stirred at 120° C. for 24 h. The reaction mixture was then diluted with water (8 mL), and the resulting precipitate was collected by filtration. The crude filtrate, 2-[4-(3,4-dichloro-phenoxy)-phenyl]-1H-imidazo[4,5-b]pyridine-5-carbonitrile (35 mg, 0.09 mmol), was treated with boron trifluoride/acetic acid complex (461 μL) and water (10 μL), and held at 115° C. for 30 min. The reaction mixture was cooled to room temperature and diluted with 4 N NaOH (10 mL). The resulting precipitate was collected by filtration, washed with water, and dried to provide 34 mg (94%) of the title compound.

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2c6e0c3e1bcd45b8adc124b33ba845ca
Source dataset
uspto-grants-2009_03
Patent number
US07504414B2

Reaction notes

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