Hydroxylamine → 4-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-1,2,5-oxadiazol-3-amine

HRID 1394170Notes

Reaction equation

HRID 1394170 reaction equation
[CH2:1]([N:3]1[C:11]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[N:5]=[C:4]1[CH2:12][C:13]#[N:14])[CH3:2].[N:15]([O-:17])=O.[Na+].[OH-].[Na+].[NH2:21]O>CO.Cl.O>[CH2:1]([N:3]1[C:11]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[N:5]=[C:4]1[C:12]1[C:13]([NH2:21])=[N:14][O:17][N:15]=1)[CH3:2]

Participants

8

Reactant 4

HCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 468352622-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)acetonitrile

Product 1

HCID 236465784-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-1,2,5-oxadiazol-3-amineYield 43%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The product from Step 3 (200 mg, 1.1 mmol) in methanol (4 ml) and 2N hydrochloric acid (4 ml) was treated portionwise with sodium nitrite (150 mg, 2.2 mmol) and stirred at room temperature for 2 hours. The pH of the mixture was adjusted to 12 by addition of 50% sodium hydroxide solution and a 50% solution of hydroxylamine in water (3 ml) was added. The mixture was heated at 90° C. for 2.5 hours and the reaction allowed to cool to room temperature. The resulting precipitate was filtered and dried in vacuo to afford the title compound (110 mg, 43%); MS (ES+) m/e 231 [M+H]+.

Workup

  1. temperatureThe mixture was heated at 90° C. for 2.5 hours
  2. temperatureto cool to room temperature
  3. filtrationThe resulting precipitate was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-2248208f4d494ca193d046809c04896f
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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