Dimethylacetamide → HCID 10179024, compound

HRID 916746Notes

Reaction equation

HRID 916746 reaction equation
NC1C=CC(C#N)=NC=1N.ClC1C=C(C=CC=1Cl)[O:15]C1C=CC(C=O)=CC=1.CN(C)C(=O)C.[Cl:34][C:35]1[CH:36]=[C:37]([CH:56]=[CH:57][C:58]=1[Cl:59])[O:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[NH:46][C:47]3[C:48]([N:55]=2)=[N:49][C:50]([C:53]#[N:54])=[CH:51][CH:52]=3)=[CH:41][CH:40]=1>O.[OH-].[Na+]>[Cl:34][C:35]1[CH:36]=[C:37]([CH:56]=[CH:57][C:58]=1[Cl:59])[O:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[NH:46][C:47]3[C:48]([N:55]=2)=[N:49][C:50]([C:53]([NH2:54])=[O:15])=[CH:51][CH:52]=3)=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 31374DimethylacetamideHCID 107069044-(3,4-dichlorophenoxy)benzaldehydeHCID 450795585,6-Diamino-2-pyridinecarbonitrileHCID 68842287HCID 68842287, compound

Product 1

HCID 10179024HCID 10179024, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
120 °C

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. filtrationthe resulting precipitate was collected by filtration
  2. waitheld at 115° C. for 30 min
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-45c729242ea64977a5f99a29b186f022
Source dataset
uspto-grants-2007_09
Patent number
US07271261B2

Reaction notes

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